(1) The CH/pi Interaction, by M. Nishio, M. Hirota, and Y. Umezawa (1998)
(2) New edition: Introduction to Intermolecular Forces in Organic Chemistry, by M. Nishio (2008)
(3) The Weak Hydrogen Bond, by G. R. Desiraju and T. Steiner (1999)
(4) Principles and Methods in Supramolecular Chemistry, by H.-J. Schneider and A. Yatsimirski (1999)
The CH/pi 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/pi interaction to facilitate a clearer common understanding of the interaction between CH bond and pi-systems.
(ISBN 0-471-25290-5, 217pp)
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.
Interested readers are advised to visit the following website (Category: books, Key word: motohiro nishio).
Please click here.
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
New edition Introduction to Intermolecular Forces in Organic Chemistry
M. Nishio, Kodansha, 2008 新版 有機化学のための分子間力入門
西尾元宏，講談社，2008
Under construction
CONTENTS
1. 物質と化学的結合力 (Chemical Bonding Forces)
1.1 物質をつくる力（Forces that Make Materials）
1.2 強い化学的結合力と弱い化学的結合力（Strong and Weak Chemical Bonds）
1.3 分子集合体の化学（Chemistry of Molecular Assemblies）
2. 分子間相互作用の基礎 (Introduction to Molecular Interactions)
2.1 主な分子間力（Important Molecular Forces）
2.2 その他の分子間相互作用（Other Weak Forces）
2.3 ４つの分子間力の比較 (Comparison of Four Molecular Forces）
2.4 疎水効果（Comment on the so-called "Hydrophobic Effect"）
3. 静電的相互作用とファンデルワールス力 (Electrostatic Interactions and van der Waals Force)
3.1 静電的相互作用（Electrostatic Interactions）
3.2 ファンデルワールス相互作用（van der Waals Interaction）
4. 水素結合 (Various Hydrogen Bonds)
4.1 水素結合の分類（Various Hydrogen Bonds）
4.2 水素結合（Hydrogen Bond）
5. ＣＨ／ｎ水素結合，ＸＨ／π水素結合（CH/n and XH/pi Hydrogen Bonds）
5.1 ＣＨ／ｎ水素結合（CH/n Hydrogen Bonds）
5.2 ＸＨ／π水素結合（XH/pi Hydrogen Bonds）
6. ＣＨ／π水素結合 (CH/pi Hydrogen Bond)
6.1 活性なＣＨとπ電子系の相互作用（Interaction of Active CHs with pi-System）
6.2 不活性なＣＨとπ電子系の相互作用（Interaction of Non acidic CHs with pi-System）
6.3 ＣＨ／π相互作用の特徴 (Characteristics of the CH/pi hydrogen bond）
7. 分子間相互作用の特徴 (Characteristics of the Weak Intermolecular Forces)
7.1 複合体の安定性（Stability of Molecular Complexes）
7.2 エンタルピー加成効果（Additive Enthalpic Effect）
7.3 エントロピー効果（Entropic Effect）
7.4 立体電子的相補性（Stereoelectronic Complementarity）
7.5 ソフトとハードの相性（HSAB Principle）
7.6 分子認識の論理（Molecular Recognition）
8. 分子間相互作用の研究法 (Methods)
8.1 分光学的方法（Spectrometries）
8.2 結晶解析（Diffraction Methods）
8.3 その他の方法（Miscellaneous Methods）
8.4 理論計算（Calculations）
8.5 結晶データベース検索（Database Analyses: The Cambridge Structural Database）
9. 立体配座と旋光現象（分子内相互作用）Conformation, chiroptical property
10. 超分子の化学 (Supramolecular chemistry)
11. 自己構造形成 (Self-assembly)
12. 分離の化学 (Chemistry of separation)
13. 有機反応の立体選択性 (Selective organic reactions)
14. 構造生物学の基礎 (Basis of structural biology)
15. 生体反応の特徴 (Characteristics of biochemical reactions)
16. 生命科学と分子間力 (Biological science and molecular forces)
図書解題 (Selected Readings)
CONTENTS
1. Introduction
2. Archetypes of the weak hydrogen bond: C-H/O and C-H/N interactions in organic and organometallic systems
3. Other weak and non-conventional hydrogen bonds
4. The weak hydrogen bond in supramolecular chemistry
5. The weak hydrogen bond in biological structures
6. Conclusions
CONTENTS
A. Basic Concepts of Host-Guest Complexation with Examples from Ionophor Chemistry
B. Non-Covalent Interactions and Organic Host-Guest Complexation
C. Medium Effects
D. Energetics of Supramolecular Complexes: Experimental Methods
E. Structural Methods
F. Dynamics of Supramolecular Systems
G. Surfactant-Based Supramolecular Systems and Dendrimers
H. Shape Recognition / Solid State Inclusion Complexes
I. Selected Applications
