Chemistry of organic fluorine compounds

Springer | August 26, 2002 | ISBN-10: 3540420649 | 368 pages | PDF | 3.09 MB
This volume, written by a range of international experts, covers a wide range of topics involving organic fluorine compounds. Each chapter is preceded by a summary and includes extensive illustrations and references. The chapters cover atmospheric chemistry, application of 19F NMR, partition, degradation and transformation, naturally occurring organic fluorine compounds, toxicology of perfluoroalkanes and phosphorofluoridates, and application of aromatic compounds to the elucidation of the mechanism of cytochrome P450.


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Aziridines and epoxides in organic synthesis

Review

"... should therefore be included in the library of every chemistry department. Experts in the field of catalysis and organic synthesis in both academia and industry will value the book as a very important "spring-loaded" source of information."
Angewandte Chemie

Product Description

Aziridines and epoxides are among the most widely used intermediates in organic synthesis, acting as precursors to complex molecules due to the strains incorporated in their skeletons. Besides their importance as reactive intermediates, many biologically active compounds also contain these three-membered rings. Filling a gap in the literature, this clearly structured book presents the much needed information in a compact and concise way. The renowned editor has succeeded in gathering together excellent authors to cover synthesis, applications, and the biological aspects in equal depth.
Divided roughly equally between aziridines and epoxides, the twelve chapters discuss:

• Synthesis of aziridines
• Nucleophilic ring-opening of aziridines and epoxides
• Organic synthesis with aziridine building blocks
• Vinyl aziridines in organic synthesis
• Diastereoselective aziridination reagents
• Synthetic aspects of aziridinomitocene chemistry
• Biosynthesis of biologically important aziridines
• Organic catalysis of epoxide and aziridine ring formation
• Metal-mediated synthesis of epoxides
• Asymmetric epoxide ring opening chemistry
• Epoxides in complex molecule synthesis
• Biological activity of epoxide-containing molecules

A high-quality reference manual for academic and industrial chemists alike.

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Product Details

• Hardcover: 516 pages
• Publisher: Wiley-VCH (March 21, 2006)
• Language: English
• ISBN-10: 3527312137
• ISBN-13: 978-3527312139

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Advanced free radical reactions for organic synthesis 2004

Review

The author has succeeded in presenting many facets of this very interesting area of chemistry in a highly engaging manner. As a result, anyone who wishes to familiarize themselves with the field of radical chemistry should take the time to look through "Advanced Free Radical Reactions for Organic Synthesis".

ORGANIC CHEMISTRY, 2005

Book Description

This title is the definitive guide to radical chemistry for all scientists.

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Product Details

• Hardcover: 270 pages
• Publisher: Elsevier Science; 1 edition (January 28, 2004)
• Language: English
• ISBN-10: 0080443745
• ISBN-13: 978-0080443744

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Structure Elucidation by NMR in Organic Chemistry

Structure Elucidation by NMR in Organic Chemistry
Publisher: Wiley | 3 edition (December 3, 2002) | ISBN: 0470850078 | Pages: 270 | PDF | 8.7 MB

This text provides the graduate student with a systematic guide to unravelling structural information from the NMR spectra of unknown synthetic and natural compounds. A brief introduction gives an overview of the basic principles and elementary instrumental methods of NMR. This is followed by instructional strategy and tactical advice on how to translate spectra into meaningful structural information. The book provides the student with 55 sets of spectra of graduated complexity. These are designed to challenge the student's problem-solving abilities by the introduction of new concepts with each group of problems, followed by possible solutions and full explanations. A formula index of solutions is provided at the end of the text. This third edition, following on from the second (a reprint of the first edition with corrections), presents significant new material. Thus, actual methods of two-dimensional NMR such as some inverse techniques of heteronuclear shift correlation, as well as the detection of proton-proton connectivities and nuclear Overhauser effects are included. To demonstrate the applications of these methods, new problems have replaced those of previous editions.

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Organic Experiments Fieser

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Modren Organic Synthesis in The Laboratory

Contents:

Abbreviations and Acronyms xv

1 Fundamental Techniques 3
1.1 Safety! 3
1.2 Useful Preparations 5
1.3 Chromatography 17
1.4 Crystallization 22
1.5 Residual Solvent Peaks in Nuclear Magnetic Resonance 24

2 Functional Group Manipulations 28
2.1 Alcohol Oxidation State 28
2.2 Ketone Oxidation State 39
2.3 Acid Oxidation State 44

3 Oxidation 55
3.1 Alcohol to Ketone Oxidation State 55
3.2 Alcohol to Acid Oxidation State 68
3.3 Olefin to Diol 70
3.4 Aldehyde to Acid Oxidation State 76
3.5 Heteroatom Oxidations 78

4 Reductions 81
4.1 Alcohols to Alkanes 81
4.2 Aldehydes, Amides, and Nitriles to Amines 83
4.3 Carboxylic Acids and Derivatives to Alcohols 85
4.4 Esters and Other Carboxylic Acid Derivatives to Aldehydes 88
4.5 Ketones or Aldehydes to Alcohols 91
4.6 Ketones to Alkanes or Alkenes 98
4.7 Reductive Dehalogenations 104
4.8 Carbon–Carbon Double and Triple Bond Reductions 105
4.9 Heteroatom–Heteroatom Reductions 108

5 Carbon−Carbon Bond Formation 111
5.1 Carbon−Carbon Forming Reactions (Single Bonds) 111
5.2 Carbon−Carbon Double Bonds (Olefin Formation) 150
5.3 Reactions that Form Multiple Carbon−Carbon Bonds 166

6 Protecting Groups 168
6.1 Alcohols and Phenols 168
6.2 Amines and Anilines 176
6.3 Aldehydes and Ketones 185

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Laboratory Experiments for General Organic and Biochemistry 4th edition

Description:
The 48 experiments in this well-conceived manual illustrate important concepts and principles in general, organic, and biochemistry. As in previous editions, three basic goals guided the development of all the experiments: (1) the experiments illustrate the concepts learned in the classroom; (2) the experiments are clearly and concisely written so that students will easily understand the task at hand, will work with minimal supervision because the manual provides enough information on experimental procedures, and will be able to perform the experiments in a 2 1/2-hour laboratory period; and, (3) the experiments are not only simple demonstrations, but also contain a sense of discovery. This edition includes many revised experiments.

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Ion-Radical Organic Chemistry Principles and Applications Second Edition

Product Details

• Pub. Date: October 2008
• Publisher: Taylor & Francis, Inc.
• Format: Hardcover, 672pp

• ISBN-13: 9780849390685
• ISBN: 0849390680
• Edition Number: 2
• Edition Description: REV

Discription:

Much new data concerning the behavior of organic ion-radicals has developed in the past few years. Consolidating knowledge from a number of disciplines, Ion-Radical Organic Chemistry: Principles and Applications, Second Edition presents the recent changes that have occurred in the field since the publication of the first edition in 2003.

This volume examines the formation, transformation, and application of ion-radicals in typical conditions of organic synthesis. Avoiding complex mathematics, the author explains the principles of ion-radical organic chemistry and presents an overview of organic ion-radical reactions. He reviews methods of determining ion-radical mechanisms and controlling ion-radical reactions. Wherever applicable, the text addresses issues relating to ecology and biomedical concerns as well as inorganic participants of the ion-radical organic reactions.

After reviewing the nature of organic ion-radicals and their ground-state electronic structure, the book discusses their formation, the relationship between electronic structure and reactivity, mechanism and regulation of reactions, stereochemical aspects, synthetic opportunities, and practical applications. Additional topics include electronic and opto-electronic devices, organic magnets and conductors, lubricants, other materials, and reactions of industrial or biomedical importance.

The book concludes by providing an outlook on possible future development in this field. Researchers and practitioners engaged in active work on synthetic or mechanistic organic chemistry and its practical applications will find this text to be invaluable in both its scope and its depth.

Contents:

Preface .......................................................................................................................................... xiii
Author .............................................................................................................................................xv
Chapter 1
Nature of Organic Ion-Radicals and Their Ground-State Electronic Structure
1.1 Introduction ...............................................................................................................................1
1.2 Unusual Features .......................................................................................................................2
1.2.1 Substituent Effects .........................................................................................................2
1.2.2 Connections between Ion-Radical Reactivity and Electronic Structure of
Ion-Radical Products .....................................................................................................7
1.2.3 Bridge-Effect Peculiarities .......................................................................................... 10
1.3 Acid–Base Properties of Organic Ion-Radicals ...................................................................... 16
1.3.1 Anion-Radicals ............................................................................................................ 16
1.3.1.1 Anion-Radical Basicity ................................................................................. 16
1.3.1.2 Pathways of Hydrogen Detachment from Anion-Radicals ...........................20
1.3.2 Cation-Radicals ...........................................................................................................22
1.3.2.1 Cation-Radical Acidity .................................................................................22
1.3.2.2 Cation-Radical Basicity ................................................................................29
1.3.2.3 Cation-Radicals as Acceptors or Donors of Hydrogen Atoms .....................30
1.4 Metallocomplex Ion-Radicals .................................................................................................30
1.4.1 Metallocomplex Anion-Radicals .................................................................................30
1.4.2 Metallocomplex Cation-Radicals ................................................................................ 33
1.4.3 Bridge Effect in Metallocomplex Ion-Radicals ...........................................................36
1.4.4 Charge-Transfer Coordination to Metallocomplex Ion-Radicals ................................38
1.5 Organic Ion-Radicals with Several Unpaired Electrons or Charges ......................................39
1.6 Polymeric Ion-Radicals ...........................................................................................................48
1.7 Inorganic Ion-Radicals in Reactions with Organic Substrates ............................................... 53
1.7.1 Superoxide Ion .............................................................................................................54
1.7.1.1 Reactions of Superoxide Ion with Organic H Acids ..................................... 55
1.7.1.2 Reactions of Superoxide Ion with Organic Electrophiles .............................56
1.7.1.3 Reactions of Superoxide Ion with Biological Objects .................................. 57
1.7.1.4 Superoxide Ion–Ozone Anion-Radical Relation .......................................... 57
1.7.2 Atomic Oxygen Anion-Radical ...................................................................................58
1.7.3 Molecular Oxygen Cation-Radical ..............................................................................58
1.7.4 Carbon Dioxide Anion-Radical ...................................................................................59
1.7.5 Carbonate Radical .......................................................................................................60
1.7.6 Sulfur Dioxide Anion-Radical .................................................................................... 61
1.7.7 Sulfi te Radical ............................................................................................................. 61
1.7.8 Sulfate Radical ............................................................................................................ 62
1.7.9 Hydroxide Anion .........................................................................................................65
1.7.10 Nitrosonium and Nitronium Ions ................................................................................66
1.7.11 Tris(aryl)amine and Thianthrene Cation-Radicals......................................................67
1.7.12 Trialkyloxonium Hexachloroantimonates ...................................................................69
1.7.13 Transition Metal Ions ...................................................................................................69
1.8 Conclusion ...............................................................................................................................73
References ....................................................................................................................................... 74
viii Contents

Chapter 2
Formation of Organic Ion-Radicals
2.1 Introduction .............................................................................................................................85
2.2 Chemical Methods of Organic Ion-Radical Preparation ........................................................86
2.2.1 Anion-Radicals ............................................................................................................86
2.2.2 Cation-Radicals ...........................................................................................................89
2.2.3 Carbenoid Ion-Radicals ...............................................................................................92
2.3 Equilibria in Liquid-Phase Electron-Transfer Reactions ........................................................93
2.4 Electrochemical Methods versus Chemical Methods .............................................................95
2.4.1 Charge-Transfer Phenomena .......................................................................................96
2.4.2 Template Effects ........................................................................................................ 100
2.4.3 Adsorption Phenomena ............................................................................................. 103
2.4.4 Stereochemical Phenomena ....................................................................................... 106
2.4.5 Concentration Effects on the Fate of Ion-Radicals at Electrodes
and in Solutions ......................................................................................................... 110
2.4.6 Aggregation of Ion-Radical Salts .............................................................................. 111
2.4.6.1 Direct Infl uence on Electron-Transfer Equilibrium .................................... 112
2.4.6.2 Electron-Transfer Reactions with Participation of Ion-Radical
Aggregates................................................................................................... 113
2.4.6.3 Kinetic and Mechanistic Differences between Electrode and
Chemical (Homogeneous) Ion-Radical Dimerization ................................ 114
2.5 Formation of Organic Ion-Radicals in Living Organisms .................................................... 115
2.6 Isotope-Containing Organic Compounds as Ion-Radical Precursors .................................. 117
2.6.1 Kinetic Isotope Effects in Electron-Transfer Reactions ............................................ 118
2.6.2 Behavior of Isotope Mixtures in Electron-Transfer Reactions ..................................120
2.7 Organic Ion-Radicals in Solid Phases ...................................................................................126
2.7.1 Organic Ion-Radicals in Frozen Solutions ................................................................126
2.7.2 Organic Ion-Radical as Constituents of Solid Salts .................................................. 130
2.8 Formation and Behavior of Ion-Radicals within Confi nes ................................................... 130
2.8.1 Micellar Media .......................................................................................................... 130
2.8.2 Porous Media ............................................................................................................. 131
2.8.3 Capsule Media ........................................................................................................... 133
2.9 Conclusion ............................................................................................................................. 135
References ..................................................................................................................................... 136

Chapter 3
Electronic Structure–Reactivity Relationship in Ion-Radical
Organic Chemistry ................................................................................................... 143
3.1 Introduction ........................................................................................................................... 143
3.2 Principle of “Detained” Electron That Controls Ion-Radical Reactivity ............................. 144
3.2.1 Frontier-Orbital Control ............................................................................................ 144
3.2.2 Steric Control over Spin Delocalization .................................................................... 153
3.2.3 Unpaired Electron Localization in the Field of Two or More Atoms ....................... 155
3.2.4 Spin–Charge Separation (Distonic Stabilization of Ion-Radicals) ........................... 161
3.2.4.1 Distonic Stabilization of Anion-Radicals ................................................... 163
3.2.4.2 Distonic Stabilization of Cation-Radicals................................................... 165
3.2.5 Ion-Pair Formation .................................................................................................... 168
3.2.5.1 Detention of Unpaired Electron in a Framework of One Specifi c
Molecular Fragment .................................................................................... 169
3.2.5.2 Formation of Closed Contour for Unpaired Electron Delocalization ......... 170
Contents ix
3.3 Principle of “Released” Electron That Controls Ion-Radical Reactivity .............................. 178
3.3.1 Effects of Spread Conjugation in Ion-Radicals Derived from Molecules
with Large Contours of Delocalization ..................................................................... 180
3.3.2 Spin Delocalization in Ion-Radicals Derived from Molecules of Increased
Dimensionality .......................................................................................................... 183
3.4 Biomedical Aspects of Ion-Radical Organic Chemistry ...................................................... 186
3.4.1 Cation-Radical Damage in Deoxyribonucleic Acid .................................................. 186
3.4.1.1 Ionization Potentials of Carcinogens .......................................................... 187
3.4.1.2 Localization of Charges and Spins in Cation-Radicals of Carcinogens ..... 187
3.4.2 On Geometrical and Spatial Factors Governing the Behavior of
Ion-Radicals in Biological Systems ........................................................................... 189
3.4.3 Ion-Radical Repair of Damaged Deoxyribonucleic Acid.......................................... 191
3.4.4 Cation-Radical Intermediates in Metabolism of Furan Xenobiotics ........................ 194
3.4.5 Behavior of Anion-Radicals in Living Organisms .................................................... 194
3.5 Conclusion ............................................................................................................................. 196
References ..................................................................................................................................... 197

Chapter 4
Discerning Mechanism of Ion-Radical Organic Reactions
4.1 Introduction ...........................................................................................................................205
4.2 Why Do Reactions Choose Ion-Radical Mechanism? ..........................................................205
4.3 Chemical Approaches to Identifi cation of Ion-Radical Organic Reactions ..........................209
4.3.1 Identifi cation According to Structure of Final Products ...........................................209
4.3.2 Identifi cation According to Correlation within Reaction Series ............................... 213
4.3.3 Identifi cation According to Disturbance of “Leaving-Group Strength”
Correlation ................................................................................................................. 215
4.3.4 Kinetic Approaches to Identifi cation of Ion-Radical Reactions ................................ 216
4.3.4.1 Kinetic Isotope Effect ................................................................................. 216
4.3.4.2 Other Kinetic Approaches .......................................................................... 217
4.3.5 Positional Reactivity and Distribution of Spin Density in
Substrate Ion-Radicals ............................................................................................... 219
4.3.6 Identifi cation by Methods of Chemical Probes .........................................................223
4.3.6.1 Initiation of Polymerization of Vinyl Additives ..........................................223
4.3.6.2 Method of Inhibitors ...................................................................................224
4.3.6.3 Method of Radical and Spin Traps .............................................................227
4.4 Physical Approaches to Identifi cation of Ion-Radical Reactions .......................................... 232
4.4.1 Radiospectroscopy..................................................................................................... 232
4.4.1.1 Electron Spin Resonance Methods ............................................................. 232
4.4.1.2 Nuclear Magnetic Resonance Methods ....................................................... 233
4.4.2 Optical Spectroscopy Methods .................................................................................236
4.4.2.1 Electron Spectroscopy ................................................................................236
4.4.2.2 Vibration Spectroscopy ...............................................................................238
4.4.3 Other Physical Methods ............................................................................................238
4.4.3.1 Magnetic Susceptibility...............................................................................238
4.4.3.2 Mass Spectrometry .....................................................................................238
4.4.3.3 Electrochemical Modeling of Ion-Radical Reactions .................................238
4.4.3.4 X-Ray Diffraction ....................................................................................... 239
4.5 Examples of Complex Approaches to Discernment of Ion-Radical
Mechanism of Organic Reactions .........................................................................................240
4.5.1 Oxidative Polymerization of Anilines .......................................................................240
4.5.2 Reactions of Hydroperoxides with Phosphites and Sulfi des ..................................... 241
x Contents
4.5.3 ter Meer Reaction ......................................................................................................243
4.5.4 Aromatic Nitration ....................................................................................................247
4.5.4.1 System of HNO3 and H2SO4 with Catalytic Amounts of HNO2 ................ 251
4.5.4.2 System of HNO3 and (CH3CO)2O ............................................................... 253
4.5.4.3 System of NaNO2 and CF3SO3H ................................................................. 253
4.5.4.4 Systems of Metal Nitrites with Oxidizers ................................................... 255
4.5.4.5 Systems of Metal Nitrates with Oxidizers ..................................................256
4.5.4.6 Systems with Tetranitromethane as Nitrating Agent .................................. 257
4.5.4.7 Systems with Participation of Nitrogen Dioxide .........................................258
4.5.4.8 Nitration and Hydroxylation by Peroxynitrite .............................................259
4.5.4.9 Gas-Phase Nitration ....................................................................................260
4.5.5 Meerwein and Sandmeyer Reactions ........................................................................262
4.6 Conclusion .............................................................................................................................263
References .....................................................................................................................................264
Chapter 5
Regulating Ion-Radical Organic Reactions
5.1 Introduction ........................................................................................................................... 271
5.2 Physical Effects ..................................................................................................................... 271
5.2.1 Effect of Light ........................................................................................................... 271
5.2.2 Effect of Electric Field .............................................................................................. 274
5.2.3 Effect of Magnetic Field ............................................................................................277
5.2.4 Effect of Microwave Field ......................................................................................... 278
5.2.5 Effect of Acoustic Field ............................................................................................. 279
5.2.6 Effect of Mechanical Action ..................................................................................... 281
5.2.6.1 Mechanochromism ......................................................................................282
5.2.6.2 Mechanopolymerization and Mechanolysis ................................................283
5.3 Effect of Chemical Additives ................................................................................................286
5.4 Solvent Effects ......................................................................................................................295
5.4.1 Static Effects ..............................................................................................................295
5.4.1.1 General Solvation ........................................................................................295
5.4.1.2 Selective Solvation and Solute-Solvent Binding .........................................297
5.4.2 Dynamic Effects ........................................................................................................ 301
5.4.2.1 Solvent Reorganization ............................................................................... 301
5.4.2.2 Solvent Polarity and Polarization ................................................................303
5.4.2.3 Solvent Internal Pressure ............................................................................304
5.4.2.4 Solvent Conformational Transition .............................................................305
5.4.2.5 Solvent Temperature ...................................................................................306
5.4.3 Liquid Crystals and Ionic Liquids as Solvents ..........................................................306
5.5 Salt Effects ............................................................................................................................308
5.5.1 Salt Effect on Spin Density Distribution ...................................................................308
5.5.2 Salt-Cage Effect Interplay ......................................................................................... 310
5.5.3 Salt Effect on Course of Ion-Radical Reactions ........................................................ 312
5.6 Conclusion ............................................................................................................................. 316
References ..................................................................................................................................... 317

Chapter 6
Stereochemical Aspects of Ion-Radical Organic Reactions
6.1 Introduction ........................................................................................................................... 323
6.2 Problem of Steric Restrictions .............................................................................................. 323
6.3 Refl ection of the Ion-Radical Step in Reaction Steric Results .............................................. 328
Contents xi
6.4 Conformational Transition of Ion-Radicals .......................................................................... 331
6.5 Space Structure and Skeletal Isomerization of Ion-Radicals ................................................ 341
6.6 Conclusion .............................................................................................................................344
References .....................................................................................................................................345

Chapter 7
Synthetic Opportunities of Ion-Radical Organic Chemistry
7.1 Introduction ...........................................................................................................................349
7.2 Reductive and Oxidative Reactions ......................................................................................349
7.2.1 Transformation of Ethylenic Ion-Radicals ................................................................349
7.2.1.1 Anion-Radicals ...........................................................................................349
7.2.1.2 Cation-Radicals ........................................................................................... 352
7.2.2 Reduction of Ketones into Alcohols .......................................................................... 352
7.2.3 Preparation of Dihydroaromatics .............................................................................. 354
7.2.4 Synthetic Suitability of (Dialkylamino)benzene Cation-Radicals ............................ 357
7.3 Ion-Radical Polymerization .................................................................................................. 358
7.3.1 Anion-Radical Polymerization .................................................................................. 358
7.3.2 Cation-Radical Polymerization ................................................................................. 359
7.3.2.1 Formation of Linear Main Chains .............................................................. 359
7.3.2.2 Formation of Cyclic and Branched Chains .................................................360
7.4 Ring Closure ......................................................................................................................... 362
7.4.1 Cation-Radical Ring Closure .................................................................................... 362
7.4.2 Anion-Radical Ring Closure .....................................................................................369
7.4.3 Ring Closure Involving Cation- and Anion-Radicals in Linked
Molecular Systems .................................................................................................... 377
7.5 Ring Opening ........................................................................................................................ 378
7.6 Fragmentation ....................................................................................................................... 379
7.6.1 Selective Oxidation .................................................................................................... 379
7.6.1.1 Selective Oxidation of Alkylbenzenes ........................................................ 379
7.6.1.2 Selective Oxidation of Dimethylimidazole ................................................. 381
7.6.2 Cation-Radical Route to Group Deprotection ........................................................... 382
7.6.2.1 Removal of Butoxycarbonyl Protective Group ........................................... 382
7.6.2.2 Removal of Methoxybenzyl Protective Group ............................................ 383
7.6.2.3 Removal of Trimethylsilyl Protective Group ..............................................384
7.6.3 Scission of Carbon–Carbon Bonds ...........................................................................384
7.6.4 Synthon-Infl uential Bond Scission ............................................................................387
7.7 Bond Formation ....................................................................................................................388
7.8 Opportunities Associated with SRN1 Reactions ....................................................................392
7.8.1 Substrate Structure .................................................................................................... 393
7.8.2 Nature of Introducing Groups ...................................................................................394
7.8.3 Reaction Medium ......................................................................................................394
7.8.4 Dark SRN1 Reactions ................................................................................................. 395
7.9 Conclusion ............................................................................................................................. 398
References ..................................................................................................................................... 398

Chapter 8
Ion-Radical Organic Chemistry in Its Practical Applicability
8.1 Introduction ...........................................................................................................................403
8.2 Organic Ion-Radicals in Microelectronics ............................................................................403
8.2.1 Ion-radical Approach to Molecular Switches and Modulators..................................403
8.2.2 Cation-Radicals of Triarylamines in Optical-Recording Media ...............................407
xii Contents
8.2.3 Ladder Polymerization of Fluoranthene-Based Cation-Radicals
as Route to Electrochromic Materials .......................................................................408
8.3 Organic Metals ......................................................................................................................409
8.4 Semiconductors ..................................................................................................................... 418
8.5 Organic Magnets ...................................................................................................................420
8.6 Lubrication in Terms of Ion-Radical Organic Chemistry .....................................................424
8.7 Ion-Radical Organic Chemistry in Its Contributions to Wood Delignifi cation and
Fossil-Fuel Desulfurization................................................................................................... 428
8.7.1 Paper Fabrication ....................................................................................................... 428
8.7.2 Manufacture of Commercial Products from Delignifi cation Wastes ........................ 433
8.7.3 Desulfurization of Fossil Fuels ................................................................................. 434
8.8 Conclusion ............................................................................................................................. 435
References ..................................................................................................................................... 435

Chapter 9
General Outlook

9.1 Importance of Ion-Radical Organic Chemistry .................................................................... 441
9.2 Scientometric Notes .............................................................................................................. 441
9.3 Prospects ...............................................................................................................................442
References .....................................................................................................................................443

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Hand book of Organic Solvent Properties

Contents:

Section I Hydrocarbons
n-Pentane
n-Hexane
n-Heptane
n-Octane
n-Nonane
n-Decane
2,2,4-Trimethyl pentane
Cyclohexane
Benzene
Toluene
Ethyl benzene
Xylene (mixed isomers)
C9 Aromatics
Tetra I i n

Section 2 Alcohols

Methanol
Ethanol
n-Propanol
i- Propanol
n-Butanol
i-Butanol
s-Butanol
n-Amyl alcohol
i-Amyl alcohol
Cyclohexanol
n-Octanol
Ethanediol
Diethylene glycol
1,2-PropanedioI

Section 3 Glycol ethers

Propylene glycol methyl ether
Ethylene glycol methyl ether
Ethylene glycol ethyl ether
Ethylene glycol monobutyl ether

Section 4 Chlorinated solvents

Methylene chloride
Chloroform
Carbon tetrachloride
1,2-DichIoroethane
1, I,1 -Trichloroethane
Trichloroethylene
Perch loroethy lene
Monochlorobenzene

Section 5 Ketones

Acetone
Methyl ethyl ketone
Methyl isobutyl ketone
Cyclohexanone
n-Methyl-2-pyrrolidone
Acetophenone

Section 6 Ethers

Diethyl ether
Diisopropyl ether
Dibutyl ether
Methyl tert butyl ether
1,4-Dioxane
Tetrahydrofuran

Section 7 Esters

Methyl acetate
Ethyl acetate
Isopropyl acetate
n-Butyl acetate
Cellosolve acetate

Section 8 Miscellaneous solvents

Dimethylformamide
Dimethylacetamide
Dimethylsul phoxide
Sulfolane
Carbon disulphide
Acetic acid
Aniline
Nitrobenzene
Morpholine
Pyridine
2-Nitropropane
Acetonitrile
Furfuraldehyde
Phenol
Water

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Aromatic Chemistry

Description:

This book provides an up-to-date and comprehensive account of aromatic chemistry. A series of chapters describes the synthesis and reactions of the major functional derivatives of benzene and the more common polycyclic systems. The concepts of aromaticity and the mechanism of aromatic substitution are discussed, as is the use of metals in the synthesis of aromatic compounds. Throughout, emphasis is placed on mechanisms. Worked problems and questions are provided to aid understanding.

In addition to providing material required by an undergraduate studying chemistry, Aromatic Chemistry is also ideal for industrial chemists seeking to update their knowledge of this important aspect of chemistry.

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Advanced Organic Chemistry : Reaction Mechanisms

Advanced Organic Chemistry : Reaction Mechanisms (Advanced Organic Chemistry Series) By Reinhard Bruckner
* Publisher: Academic Press
* Number Of Pages: 512
* Publication Date: 2001-07
* ISBN / ASIN: 0121381102

Book Description
A best-selling mechanistic organic chemistry text in Germany, this text's translation into English fills a long-existing need for a modern, thorough and accessible treatment of reaction mechanisms for students of organic chemistry at the advanced undergraduate and graduate level. Knowledge of reaction mechanisms is essential to all applied areas of organic chemistry; this text fulfills that need by presenting the right material at the right level.

Contents:
Preface to the English Edition, Pages xvii-xviii
Preface to the German Edition, Pages xix-xxi
Acknowledgments, Page xxiii
1 -Radical Substitution Reactions at the Saturated C Atom

2 -Nucleophilic Substitution Reactions at the Saturated C Atom

3 -Additions to the Olefinic C=C Double Bond

4 -β-Eliminations

5 -Substitution Reactions on Aromatic Compounds

6 -Nucleophilic Substitution Reactions on the Carboxyl Carbon (Except through Enolates)

7 -Additions of Heteroatom Nucleophiles to Heterocumulenes. Additions of Heteroatom Nucleophiles to Carbonyl Compounds and Follow-up Reactions,

8 -Addition of Hydride Donors and Organometallic Compounds to Carbonyl Compounds

9 -Reaction of Ylides with Saturated or α,β-Unsaturated Carbonyl Compounds

10 -Chemistry of the Alkaline Earth Metal Enolates

11-Rearrangements

12 -Thermal Cycloadditions,

13 -Transition Metal-Mediated Alkenylations, Arylations, and Alkynylations

14 -Oxidations and Reductions

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Dean Hand Book Of Organic Chemistry 2nd Ed

Product Details

• Pub. Date: June 2003
• Publisher: McGraw-Hill Companies, The
• Format: Hardcover, 800pp

• ISBN-13: 9780071375931
  
• ISBN: 0071375937
• Edition Number: 2
• Edition Description: REV

this revised edition of Dean's Handbook of Organic Chemistry delivers comprehensive coverage, with practical information, key equations and tables, and a thorough introduction to each topic. Edited by a renowned expert in organic chemistry, this book updates:

* Biopolymers
* Electronegativity
* Nomenclatures for supramolecular compounds
* Properties tables for atoms, radicals, and bonds
* Line-angle structural drawings
* And much, much more! No matter if you're a chemist, a chemical or environmental engineer, or even a student, Dean's Handbook of Organic Chemistry will add precision, insight, and a host of timesaving tips to your efforts. Complete Coverage of:
* Organic compounds
* Inorganic compounds
* Properties of atoms, radicals, and bonds
* Physical properties
* Thermodynamic properties
* Spectroscopy
* Physicochemical relationships
* Electrolytes, electromotive force, and chemical equilibrium
* Laboratory manipulations
* Polymers, rubbers, fats, oils, and waxes
Gokel (Washington Univ., St. Louis) has prepared a new edition (1st ed., 1987) of a useful handbook that students and researchers will find extremely valuable. It is a convenient reference work that provides tables for physical constants of organic and inorganic compounds as well as spectral data and thermodynamic properties; these sections make up the bulk of the manual. There are more than a thousand pages of tabled data, divided into 11 sections: organic compounds; inorganic and organometallic compounds; properties of atoms, radicals, and bonds; physical properties; thermodynamic properties; spectroscopy; physiochemical relationships; electrolytes, electromotive force, and chemical equilibrium; data useful in laboratory manipulations and analysis; polymers, rubbers, fats, oils, and waxes; abbreviations, constants, and conversion factors. Easy-to-use index. Summing Up: Recommended. Graduate students through professionals.



Contents
Preface ............................................................................. iv
About the Author .............................................................v

1. Organic Compounds ................................... 1.1

Nomenclature of Organic Compounds ..................... ... 1.2
Hydrocarbons and Heterocycles ................................... 1.2
Table 1.1 Names of Straight-Chain Alkanes ................ 1.2
Table 1.2 Fused Polycyclic Hydrocarbons .................... 1.8
Table 1.3 Specialist Nomenclature for
Heterocyclic Systems ..................................................... 1.12
Table 1.4 Suffixes for Specialist Nomenclature
of Heterocyclic Systems ................................................. 1.12
Table 1.5 Trivial Names of Heterocyclic
Systems Suitable for Use in Fusion
Names ................................................................................ 1.13
Table 1.6 Trivial Names for Heterocyclic
Systems That Are Not Recommended for
Use in Fusion Names ........................................................ 1.16
Functionalized Compounds .............................................. 1.18
Table 1.7 Characteristic Groups for Substitutive
Nomenclature ..................................................................... 1.19
Table 1.8 Characteristic Groups Cited Only as
Prefixes in Substitutive Nomenclature ............................ 1.21
Table 1.9 Functional Class Names Used in
Radicofunctional Nomenclature ......................................... 1.24
iv Contents
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Specific Functionalized Groups ........................................... 1.25
Table 1.10 Retained Trivial Names of Alcohols
and Phenols with Structures ................................................ 1.26
Table 1.11 Names of Some Carboxylic Acids ...................... 1.33
Table 1.12 Parent Structures of Phosphorus-
Containing Compounds ............................................................ 1.40
Table 1.13 .................................................................................. 1.44
Stereochemistry ........................................................................ 1.47
Chemical Abstracts Indexing System .................................... 1.60
Physical Properties of Pure Substances .................................. 1.61
Table 1.14 Empirical Formula Index for Organic
Compounds ................................................................................... 1.61
Table 1.15 Physical Constants of Organic
Compounds ................................................................................... 1.80

2. Inorganic and Organometallic Compounds .......... 2.1

Table 2.1 Physical Constants of Inorganic
Compounds ....................................................................................... 2.2

3. Properties of Atoms, Radicals, and Bonds .............. 3.1

Nuclides ............................................................................................. 3.2
Table 3.1 Table of Nuclides ............................................................. 3.2
Electronegativity ............................................................................... 3.9
Table 3.2A Electronegativities of the Elements ........................... 3.10
Table 3.2B Electronegativities of the Groups ............................... 3.10
Electron Affinity ................................................................................ 3.11
Table 3.3 Electron Affinities of Elements,
Radicals, and Molecules .................................................................... 3.11
Bond Lengths and Strengths ............................................................ 3.13
Table 3.4A Bond Lengths between Carbon and
Other Elements ................................................................................... 3.14
Contents v
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Table 3.4B Bond Lengths between Elements
Other Than Carbon .............................................................................. 3.17
Table 3.5 Bond Strengths .................................................................... 3.19
Bond and Group Dipole Moments ...................................................... 3.30
Table 3.6 Bond Dipole Moments ................................. 3.30
Table 3.7 Group Dipole Moments ................................ 3.31

4. Physical Properties ................................................. 4.1

Solubilities ............................................................................. 4.2
Table 4.1 Solubility of Gases in Water ......................... 4.2
Vapor Pressures .................................................................... 4.8
Table 4.2 Vapor Pressure of Mercury .......................... 4.8
Table 4.3 Vapor Pressure of Water for
Temperatures from –10 to 120°C .......................... 4.10
Table 4.4 Vapor Pressure of Deuterium Oxide ............ 4.12
Boiling Points ......................................................................... 4.12
Table 4.5A Boiling Points for Common Organic
Solvents ................................................................ 4.12
Table 4.5B Boiling Points for Common Organic
Solvents ................................................................ 4.15
Table 4.5C Boiling Point for Common Organic
Solvents ................................................................ 4.17
Table 4.6 Molecular Elevation of the Boiling
Point ...................................................................... 4.23
Table 4.7 Binary Azeotropic (Constant-Boiling)
Mixtures ................................................................. 4.25
Table 4.8 Ternary Azeotropic Mixtures ........................ 4.46
Freezing Points ..................................................................... 4.52
Tables 4.9A and B Molecular Lowering of the
Melting or Freezing Point ....................................... 4.52
Viscosity, Dielectric Constant, Dipole Moment, Surface
Tension, and Refractive Index ........................................ 4.55
vi Contents
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Table 4.10 Viscosity, Dielectric Constant, Dipole
Moment and Surface Tension of Selected
Organic Substances .............................................. 4.57
Table 4.11 Viscosity, Dielectric Constant, Dipole
Moment, and Surface Tension of Selected
Inorganic Substances ............................................ 4.94
Table 4.12 Refractive Index, Viscosity, Dielectric
Constant, and Surface Tension of Water at
Various Temperatures ........................................... 4.98
Combustible Mixtures ............................................................ 4.99
Table 4.13 Properties of Combustible Mixtures
in Air ...................................................................... 4.99

5. Thermodynamic Properties .................................... 5.1

Enthalpies and Gibbs (Free) Energies of Formation,
Entropies, and Heat Capacities ...................................... 5.2
Table 5.1 Enthalpies and Gibbs (Free) Energies
of Formation, Entropies, and Heat Capacities
of Organic Compounds .......................................... 5.3
Table 5.2 Heats of Melting and Vaporization
(or Sublimation) and Specific Heat at Various
Temperatures of Organic Compounds ................... 5.44
Critical Phenomena ............................................................... 5.75
Table 5.3 Critical Properties ........................................ 5.75
Table 5.4 Group Contributions for the Estimation
of Critical Properties .............................................. 5.88

6. Spectroscopy ........................................................... 6.1

Ultraviolet-Visible Spectroscopy ........................................... 6.3
Table 6.1 Electronic Absorption Bands for
Representative Chromophores .............................. 6.5
Table 6.2 Ultraviolet Cutoffs of Spectrograde
Solvents ................................................................ 6.6
Contents vii
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Table 6.3 Absorption Wavelength of Dienes ................ 6.7
Table 6.4 Absorption Wavelength of Enones and
Dienones ............................................................... 6.7
Table 6.5 Solvent Correction for UV–VIS
Spectroscopy ......................................................... 6.8
Table 6.6 Primary Band of Substituted Benzene
and Heteroaromatics ............................................. 6.9
Table 6.7 Wavelength Calculation of the Principal
Band of Substituted Benzene Derivatives .............. 6.9
Photoluminescence ............................................................... 6.10
Table 6.8 Fluorescence Spectroscopy Data of
Some Organic Compounds .................................... 6.11
Table 6.9 Fluorescence Quantum Yield Values ........... 6.17
Table 6.10 Phosphorescence Spectroscopy of
Some Organic Compounds .................................... 6.17
Infrared Spectroscopy ........................................................... 6.21
Table 6.11 Absorption Frequencies of Single
Bonds to Hydrogen ................................................ 6.21
Table 6.12 Absorption Frequencies of Triple
Bonds .................................................................... 6.28
Table 6.13 Absorption Frequencies of Cumulated
Double Bonds ........................................................ 6.29
Table 6.14 Absorption Frequencies of Carbonyl
Bonds .................................................................... 6.31
Table 6.15 Absorption Frequencies of Other
Double Bonds ........................................................ 6.35
Table 6.16 Absorption Frequencies of Aromatic
Bonds .................................................................... 6.39
Table 6.17 Absorption Frequencies of
Miscellaneous Bands ............................................. 6.40
Table 6.18 Absorption Frequencies in the Near
Infrared .................................................................. 6.47
viii Contents
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Table 6.19 Infrared Transmitting Materials .................. 6.49
Table 6.20 Infrared Transmission Characteristics
of Selected Solvents .............................................. 6.51
Raman Spectroscopy ............................................................ 6.54
Table 6.21 Raman Frequencies of Single Bonds
to Hydrogen and Carbon ....................................... 6.54
Table 6.22 Raman Frequencies of Triple Bonds .......... 6.59
Table 6.23 Raman Frequencies of Cumulated
Double Bonds ........................................................ 6.60
Table 6.24 Raman Frequencies of Carbonyl
Bonds .................................................................... 6.61
Table 6.25 Raman Frequencies of Other Double
Bonds .................................................................... 6.63
Table 6.26 Raman Frequencies of Aromatic
Compounds ........................................................... 6.66
Table 6.27 Raman Frequencies of Sulfur
Compounds ........................................................... 6.67
Table 6.28 Raman Frequencies of Ethers ................... 6.69
Table 6.29 Raman Frequencies of Halogen
Compounds ........................................................... 6.70
Table 6.30 Raman Frequencies of Miscellaneous
Compounds ........................................................... 6.71
Nuclear Magnetic Resonance Spectroscopy ....................... 6.71
Table 6.31 Nuclear Properties of the Elements ........... 6.73
Table 6.32 Proton Chemical Shifts of Reference
Compounds Relative to Tetramethylsilane ............. 6.74
Table 6.33 Common NMR Solvents ............................ 6.75
Table 6.34 Proton Chemical Shifts .............................. 6.76
Table 6.35 Estimation of Chemical Shift for
Proton of —CH2— and >CH— Groups .................. 6.79
Table 6.36 Estimation of Chemical Shift of Proton
Attached to a Double Bond .................................... 6.80
Contents ix
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Table 6.37 Chemical Shifts in Monosubstituted
Benzene ................................................................ 6.81
Table 6.38 Proton Spin Coupling Constants ................ 6.82
Table 6.39 Carbon-13 Chemical Shifts ........................ 6.83
Table 6.40 Estimation of Chemical Shifts of
Alkane Carbons ..................................................... 6.86
Table 6.41 Effect of Substituent Groups on Alkyl
Chemical Shifts ...................................................... 6.87
Table 6.42 Estimation of Chemical Shift of
Carbon Attached to a Double Bond ....................... 6.88
Table 6.43 Carbon-13 Chemical Shifts in
Substituted Benzenes ............................................ 6.89
Table 6.44 Carbon-13 Chemical Shifts in
Substituted Pyridines ............................................. 6.90
Table 6.45 Carbon-13 Chemical Shifts of
Carbonyl Group ..................................................... 6.91
Table 6.46 One-Bond Carbon–Hydrogen Spin
Coupling Constants ............................................... 6.92
Table 6.47 Two-Bond Carbon–Hydrogen Spin
Coupling Constants ............................................... 6.93
Table 6.48 Carbon–Carbon Spin Coupling
Constants .............................................................. 6.93
Table 6.49 Carbon–Fluorine Spin Coupling
Constants .............................................................. 6.94
Table 6.50 Carbon-13 Chemical Shifts of
Deuterated Solvents .............................................. 6.95
Table 6.51 Carbon-13 Spin Coupling Constants
with Various Nuclei ................................................ 6.96
Table 6.52 Boron-11 Chemical Shifts .......................... 6.96
Table 6.53 Nitrogen-15 (or Nitrogen-14) Chemical
Shifts ..................................................................... 6.97
x Contents
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Table 6.54 Nitrogen-15 Chemical Shifts in
Monosubstituted Pyridine ...................................... 6.100
Table 6.55 Nitrogen-15 Chemical Shifts for
Standards .............................................................. 6.101
Table 6.56 Nitrogen-15 to Hydrogen-1 Spin
Coupling Constants ............................................... 6.101
Table 6.57 Nitrogen-15 to Carbon-13 Spin
Coupling Constants ............................................... 6.102
Table 6.58 Nitrogen-15 to Fluorine-19 Spin
Coupling Constants ............................................... 6.102
Table 6.59 Fluorine-19 Chemical Shifts ....................... 6.102
Table 6.60 Fluorine-19 Chemical Shifts for
Standards .............................................................. 6.104
Table 6.61 Fluorine-19 to Fluorine-19 Spin
Coupling Constants ............................................... 6.104
Table 6.62 Silicon-29 Chemical Shifts ......................... 6.104
Table 6.63 Phosphorus-31 Chemical
Shifts ..................................................................... 6.105
Table 6.64 Phosphorus-31 Spin Coupling
Constants .............................................................. 6.109
Electron Spin Resonance ...................................................... 6.110
Table 6.65 Spin–Spin Coupling (Hyperfine
Splitting Constants) ............................................... 6.111
Ionization Potentials .............................................................. 6.114
Table 6.66A Ionization Potentials of Molecular
Species ................................................................. 6.114
Table 6.66B Alphabetical Listing of Ionization
Potentials of Molecular Species ............................. 6.120
Table 6.67 Ionization Potentials of Radical
Species ................................................................. 6.122
X-Ray Diffraction ................................................................... 6.122
Contents xi
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7. Physiochemical Relationships ............................... 7.1

Linear Free Energy Relationships ......................................... 7.2
Table 7.1 Hammett and Taft Substituent
Constants .............................................................. 7.3
Table 7.2 pKA and Rho (p) Values for the
Hammett Equation ................................................. 7.8
Table 7.3 pKA and Rho (p) Values for the Taft
Equation ................................................................ 7.10
Table 7.4 Special Hammett Sigma
Constants .............................................................. 7.10
8. Electrolytes, Electromotive Force, and

Chemical Equilibrium .............................................. 8.1

Equilibrium Constants ........................................................... 8.2
Table 8.1 pKA Values of Organic Materials in
Water at 25°C ........................................................ 8.3
Table 8.2 Proton-Transfer Reactions of Inorganic
Materials in Water at 25°C ..................................... 8.61
Table 8.3 Selected Equilibrium Constants in
Aqueous Solution at Various Temperatures ........... 8.64
Table 8.4 Indicators for Aqueous Acid–Base
Titrations ............................................................... 8.72
Buffer Solutions ..................................................................... 8.74
Table 8.5 National Institute of Standards and
Technology (Formerly National Bureau of
(Standards U.S.)) Reference pH Buffer
Solutions ................................................................ 8.74
Table 8.6 Compositions of National Institute of
Standards and Technology. Standard pH
Buffer Solutions ..................................................... 8.75
Table 8.7 pH Values of Buffer Solutions for
Control Purposes ................................................... 8.76
xii Contents
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Reference Electrodes ............................................................ 8.77
Table 8.8 Potentials of Reference Electrodes (in
Volts) as a Function of Temperature ...................... 8.77
Table 8.9 Potentials of Reference Electrodes (in
Volts) at 25°C for Water–Organic Solvent
Mixtures ................................................................. 8.79
Electrode Potentials .............................................................. 8.80
Table 8.10 Potentials of Selected Half-Reactions
at 25°C .................................................................. 8.80
Table 8.11 Half-Wave Potentials (vs. Saturated
Calomel Electrode) of Organic Compounds
at 25°C .................................................................. 8.82
9. Data Useful in Laboratory Manipulations and

Analysis .................................................................... 9.1

Cooling Mixtures .................................................................... 9.2
Table 9.1 Cooling Mixtures Made from Dry Ice
and Salts ............................................................... 9.2
Table 9.2 Dry Ice or Liquid Nitrogen Slush Baths ........ 9.2
Humidification and Drying ..................................................... 9.2
Table 9.3 Humidity (%) Maintained by Saturated
Solutions of Various Salts at Specified
Temperatures ........................................................ 9.3
Table 9.4 Humidity (%) Maintained by Saturated
Solutions of Common Salts at Specified
Temperatures ........................................................ 9.3
Table 9.5 Drying Agents .............................................. 9.4
Separation Methods .............................................................. 9.5
Table 9.6 Solvents of Chromatographic Interest .......... 9.5
Table 9.7 Solvents Having the Same Refractive
Index and the Same Density at 25°C ..................... 9.7
Contents xiii
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Table 9.8 McReynolds’ Constants for Stationary
Phases in Gas Chromatography ............................ 9.10

10. Polymers, Rubbers, Fats, Oils, and Waxes ........... 10.1

Polymers ................................................................................ 10.2
Table 10.1 Plastic Families ......................................... 10.7
Formulas and Key Properties of Plastic Materials ................ 10.9
Table 10.2 Properties of Commercial Plastics ............. 10.24
Formulas and Advantages of Rubbers ................................. 10.60
Table 10.3 Properties of Natural and Synthetic
Rubbers ................................................................. 10.64
Chemical Resistance ............................................................ 10.65
Table 10.4 Resistance of Selected Polymers and
Rubbers to Various Chemicals at 20°C .................. 10.65
Table 10.5 Common Abbreviations Used in
Polymer Chemistry ................................................ 10.67
Gas Permeability ................................................................... 10.70
Table 10.6 Gas Permeability Constants (1010P) at
25°C for Polymers and Rubbers ............................ 10.70
Table 10.7 Vapor Permeability Constants (1010P)
at 35°C for Polymers ............................................. 10.73
Fats, Oils, and Waxes ........................................................... 10.73
Table 10.8 Constants of Fats and Oils ........................ 10.73
Table 10.9 Constants of Waxes .................................. 10.76
11. Abbreviations, Constants, and Conversion

Factors ...................................................................... 11.1

Physical Constants ................................................................ 11.2
Table 11.1 Fundamental Physical Constants ............... 11.2
Greek Alphabet ..................................................................... 11.5
Table 11.2 Greek Alphabet .......................................... 11.5
xiv Contents
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Prefixes .................................................................................. 11.5
Table 11.3 Prefixes for Naming Multiples and
Submultiples of Units ............................................. 11.5
Table 11.4 Numerical Prefixes .................................... 11.5
Transformations .................................................................... 11.6
Table 11.5 Conversion Formulas for Solutions
Having Concentrations Expressed in Various
Ways ..................................................................... 11.6
Table 11.6 Conversion Factors ................................... 11.7
Statistics ................................................................................ 11.14
Table 11.7 Values of t ................................................. 11.14
Index ................................................................................ I.1

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Hetrocyclic Chemistry At A glance

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An understanding of the chemistry of heterocycles is essential in the study and application of organic chemistry, as well as being a central part of the increasingly popular medicinal and pharmaceutical chemistry degree courses. Heterocyclic Chemistry at a Glance provides a concise overview of the main principles and reactions of heterocyclic chemistry, for students studying chemistry and related courses at undergraduate level. Based on the highly successful and student friendly "at a glance" approach, the material developed in this book has been chosen to help the student grasp the essence of heterocyclic chemistry, ensuring that they can confidently use that knowledge when required. Students wanting an accessible overview of heterocyclic chemistry will find this book an ideal source of the information they require. In addition the structure of the book, which facilitates the rapid assimilation, understanding and recall of critical concepts, facts and definitions, will provide an invaluable aid to revision for students preparing for examinations.

Link updated  18-10-2010
 

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Wilson & Gisvold’s Textbook of Organic Medicinal and Pharmaceutical Chemistry 11th Edition

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Wilson & Gisvold’s Textbook of Organic Medicinal and Pharmaceutical Chemistry (Wilson and Gisvold’s Textbook of Organic and Pharmaceutical Chemistry)
By John Block, John M Beale

Publisher: Lippincott Williams & Wilkins
Number Of Pages: 1000
Publication Date: 2003-12-01
ISBN-10 / ASIN: 0781734819
ISBN-13 / EAN: 9780781734813

Book Description:

Oregon State Univ., Corvallis. Blends the chemical and pharmaceutical principles necessary for understanding structure-activity relationships and molecular mechanisms of drug action. Offers new information on emerging trends and advances and the challenges posed by new diseases. Features a new chapter on combinatorial chemistry. Previous edition: c1998. DNLM: Chemistry, Pharmaceutical.

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Advanced Organic Chemistry, Fourth Edition - Part B: Reaction and Synthesis

The control of reactivity to achieve specific syntheses is one of the overarching goals of organic chemistry. In the decade since the publication of the third edition, major advances have been made in the development of efficient new methods, particularly catalytic processes, and in means for control of reaction stereochemistry. This volume assumes a level of familiarity with structural and mechanistic concepts comparable to that in the companion volume, Part A, Structures and Mechanisms. Together, the two volumes are intended to provide the advanced undergraduate or beginning graduate student in chemistry with a sufficient foundation to comprehend and use the research literature in organic chemistry.

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Advanced Organic Chemistry: Structure and Mechanisms (Part A) (Advanced Organic Chemistry / Part A: Structure and Mechanisms)

Since its original appearance in 1977, Advanced Organic Chemistry has found wide use as a text providing broad coverage of the structure, reactivity and synthesis of organic compounds. The Fourth Edition provides updated material but continues the essential elements of the previous edition. The material in Part A is organized on the basis of fundamental structural topics such as structure, stereochemistry, conformation and aromaticity and basic mechanistic types, including nucleophilic substitution, addition reactions, carbonyl chemistry, aromatic substitution and free radical reactions. The material in Part B is organized on the basis of reaction type with emphasis on reactions of importance in laboratory synthesis. As in the earlier editions, the text contains extensive references to both the primary and review literature and provides examples of data and reactions that illustrate and document the generalizations. While the text assumes completion of an introductory course in organic chemistry, it reviews the fundamental concepts for each topic that is discussed.
The Fourth Edition updates certain topics that have advanced rapidly in the decade since the Third Edition was published, including computational chemistry, structural manifestations of aromaticity, enantioselective reactions and lanthanide catalysis.
The two parts stand alone, although there is considerable cross-referencing. Part A emphasizes quantitative and qualitative description of structural effects on reactivity and mechanism. Part B emphasizes the most general and useful synthetic reactions. The focus is on the core of organic chemistry, but the information provided forms the foundation for future study and research in medicinal and pharmaceutical chemistry, biological chemistry and physical properties of organic compounds.

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