Hard and Soft Acids and Bases Principle in Organic Chemistry

1st Edition - January 28, 1977
Author: Tse-Lok Ho
Language: English
eBook ISBN:
9 7 8 - 0 - 3 2 3 - 1 4 0 9 6 - 6

Hard and Soft Acids and Bases Principle in Organic Chemistry deals with various phenomena in organic chemistry that are directly related to or derived from the hard and soft acids… Read more

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Hard and Soft Acids and Bases Principle in Organic Chemistry deals with various phenomena in organic chemistry that are directly related to or derived from the hard and soft acids and bases (HSAB) principle. Topics covered range from chemical reactivity to displacement reactions, along with various HSAB principle applications. This text consists of 11 chapters and begins with a historical overview of the HSAB concept, followed by a classification of hard and soft acids and bases and their theoretical descriptions. The reader is methodically introduced to the stability of organic compounds and complexes; displacement reactions of HSAB; and the chemistry of alkenes, aromatic, and heterocyclic compounds. The reactivity of organophosphorus and carbonyl compounds; organosulfur compounds and other chalcogenides; and organoboranes is also considered. The book concludes with an evaluation of other applications of the HSAB principle, paying particular attention to solubility and protonation; carbenes and nitrenes; the organic chemistry of group IV elements; and the reactions of organohalides, Grignard, and related agents. This book is intended for senior undergraduates or graduate chemistry majors, as well as organic chemists who are not familiar with the HSAB concept.

Preface

1 Introduction

1.1. Definitions of Acids and Bases

1.2. The Hard and Soft Acids and Bases (HSAB) Concept: Historical Development

References

2 Classification of Hard and Soft Acids and Bases

2.1. Pearson's Generalization

2.2. Softness Scales

2.3. Theoretical Descriptions of HSAB

References

3 Chemical Reactivity

3.1. Stability of Organic Compounds and Complexes

3.2. Symbiosis

3.3. Intrinsic Strength

References

4 Displacement Reactions

4.1. General Mechanisms

4.2. Nucleophilic Reactivity

4.3. Formation and Cleavage of O-Alkyl Bond of Carboxylic Esters

4.4. Multicentered Reactions: Saville's Rules

4.5. Ambident Reactivity

References

5 Alkene Chemistry

5.1. Formation of Olefinic Linkages by Elimination Reactions. Elimination vs. Substitution

5.2. Addition to Double Bonds

5.3. Oxidation

5.4. Miscellaneous Reactions

References

6 Aromatic and Heterocyclic Chemistry

6.1. Exchange Reactions

6.2. Electrophilic Substitutions

6.3. Nucleophilic Substitutions

6.4. Ambident Behavior of Heterocyclic Compounds

6.5. Aromatic Claisen Rearrangements

6.6. Oxidative Coupling of Phenols

References

7 Reactivity of Carbonyl Compounds

7.1. The Carbonyl Group as a Hard Acceptor and a Hard Donor

7.2. The Carbonyl Oxygen as a Soft Acceptor

7.3. Reactions of α,β-Unsaturated Carbonyl Compounds

7.4. Aspects of Some Carboxylic Acid Derivatives

7.5. Some Carbonyl-Forming Processes

References

8 Organophosphorus Reactions

8.1. General Considerations

8.2. Trivalent Phosphorus Compounds as Nucleophiles

8.3. Nucleophilic Attack on the Phosphorus Center

References

9 Reactions of Organosulfur Compounds and Other Chalcogenides

9.1. Chemical Selectivity of Organic Chalcogenides

9.2. Divalent Sulfur Compounds as Soft Donors

9.3. Divalent Sulfur Compounds as Soft Acceptors

9.4.Chemistry of the Sulfinyl Group

9.5. Reactions of Higher Valent Sulfur Derivatives

References

10 Organoboron Chemistry

10.1. Stability of Organoboranes. Exchange Reactions

10.2. Hydroboration

10.3. Reactions of Arylboron Compounds

10.4. Some Aspects of Organoaluminum Reactions

References

11 Other Applications of the HSAB Principle

11.1. Solubility and Protonation

11.2. Carbenes and Nitrenes

11.3. Organic Chemistry of Group IV Elements

11.4. Reactions of Organohalides, Grignard and Related Reagents

11.5. Exceptions

References

Addendum

Author Index

Subject Index