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A comprehensive monograph

THE CH/π INTERACTION

Evidence, Nature, and Consequences
M. Nishio, M., Hirota, Y. Umezawa, 1998, Wiley-VCH, New York
ISBN-10: 0471252905
ISBN-13: 978-0471252900

A systematic exploration of the fascinating area of CH/π interaction - from the frontier of chemical research.
The CH/π bond may be the weakest of the hydrogen bonds, but it has been found to play important roles in the physical, chemical, and biological properties of a variety of substances. This book offers a complete overview of the experimental basis, theoretical background, and nature of the CH/π interaction to facilitate a clearer common understanding of the interaction between CH bond and π-systems.

タイトル

Review by G. R. Desiraju (Chemistry in Britain, March 1999, p. 63)

The term 'CH-p interaction' was coined and popularized by Nishio and coworkers in two reviews that appeared in Tetrahedron in 1989 and 1995. This book is, in many ways, an extension of these reviews. With the current intense interest in molecular association, crystal engineering and other supramolecular phenomena, any book on intermolecular interactions is bound to attract attention. When the interaction is very feeble, its interpretation can become subjective and contentious. Given these difficulties, the authors have done a reasonable job. .....

..... A proper understanding of the gray area between the weak hydrogen bond and the van der Waals interaction is elusive and remains one of the more challenging goals in modern structural chemistry. This book is far from being the definitive work in the area but, all in all, researchers and students will find it interesting and purchase by libraries is generally recommended.

CONTENTS

Chapter 1. Introduction

1-1. Importance of Weak Intermolecular Interactions

1-2. History

1-3. Scope of the Monograph

Chapter 2. Evidence and Methods of Detection

2-1. Infrared Spectroscopy

2-2. Nuclear Magnetic Resonance Spectroscopy

2-3. Circular Dichroism

2-4. X-Ray Crystallography

2-5. Miscellaneous Methods

Chapter 3. Quantum Mechanical Treatment of CH/p Interaction

3-1. Introduction

3-2. Molecular Orbital Calculations of CH/p and Other Weak Interactions

3-3. Substituent Effects as Probes to Assess the Nature of CH/p Interaction

3-4. Nature of the CH/p interaction

Chapter 4. Comparison with Other Types of Weak Molecular Interactions

4-1. CH/Y Hydrogen Bonds

4-2. XH/p interactions

4-3. Weak Coulombic Interactions

4-4. Hydrophobic Interaction

Chapter 5. Conformational Consequences

5-1. Conformation of 1,5-hexadienes

5-2. Substituent effect on Conformational Energies in Atropisomerism

5-3. Conformation of Various Organic Compounds

Chapter 6. Chiroptical Properties

6-1. Chiroptical Properties of 1,3-Cylohexadienes

6-2. Chiroptical Properties of Olefinic Compounds

6-3. Chiroptical Properties of Cyclic Ketones

Chapter 7. Selectivity in Organic Reactions

7-1. Diastereoface-Differentiating Reactions

7-2. Remote Functionalization Reactions

7-3. Enantioface-Differentiating Reactions

7-4. Coupling Reactions

Chapter 8. Crystal Structures of Clathrates

Chapter 9. Inclusion Compounds

9-1. Cyclodextrin Complexes

9-2. Calixarene Complexes

9-3. Caviplexes

9-4. Cyclophane Complexes

9-5. Pseudorotaxanes

9-6. Catenanes

Chapter 10. Interligand Interactions in Coordination Chemistry

10-1. Crystal Structures of Coordination Compounds

10-2. Conformation of Coordination Compounds

10-3. Selectivity in the Formation of Coordination Compounds

Chapter 11. Specific Interactions in Protein Structures

11-1. General Considerations

11-2. Exploring the Possibility of CH/p Interactions in Protein Crystal Data

11-3. Interactions in Hemoglobin

11-4. Interactions Involving Carbohydrates

11-5. Interactions Involving Lysine and Arginine

11-6. Comments on the So-Called Cation/p Interaction

11-7. Aromatic/Aromatic Interaction

11-8. Other Possibilities

Chapter 12. Summary and Prospects

12-1. Possibilities in Biochemistry

12-2. Possibilities in Materials Science

12-3. Conclusion