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Non-covalent Interactions in the Synthesis and Design of New Compounds



Non-covalent Interactions in the Synthesis and Design of New Compounds


This book aims to overview the role of non-covalent interactions, such as hydrogen and halogen bonding, π-π, π-anion and electrostatic interactions, hydrophobic effects and van der Waals forces in the synthesis of organic and inorganic compounds, as well as in design of new crystals and function materials. The proposed book should allow to combine, in a systematic way, recent advances on the application of non-covalent interactions in synthesis and design of new compounds and functional materials with significance in Inorganic, Organic, Coordination, Organometallic, Pharmaceutical, Biological and Material Chemistries. Therefore, it should present a multi- and interdisciplinary character assuring a rather broad scope. We believe it will be of interest to a wide range of academic and research staff concerning the synthesis of new compounds, catalysis and materials. Each chapter will be written by authors who are well known experts in their respective fields.

Notes on Editors ix

List of Contributors xi

Preface xv

Part I Organic Synthesis 1

1 Activation of Covalent Bonds Through Non‐Covalent Interactions 3
Abel M. Maharramov, Kamran T. Mahmudov, Maximilian N. Kopylovich, M. Fátima C. Guedes da Silva, and Armando J. L. Pombeiro

2 Boron–Nitrogen Bond: A Useful Molecular Construction Tool 23
João P. M. Antonio, Gonçalo D. V. Farias, Fábio M. F. Santos, Rudi Oliveira, Pedro M. S. D. Cal, and Pedro M. P. Gois

3 Influence of Steric, Electronic, and Molecular Preorganization Effects in the Reactivity of β‐Phenylethylamines with Nonenolizable Aldehydes 49
Rodolfo Quevedo

4 Non‐Covalent Interactions in the Synthesis of Macrocycles 63
Evgeny A. Kataev

Part II Inorganic, Coordination and Organometallic Syntheses 83

5 Non‐Covalent Interactions of Water with Metal Complexes in Solution 85
Antonio Romerosa and Franco Scalambra

6 π–π Interaction Directed Applications of Metal Complexes 101
Manas Sutradhar and Armando J. L. Pombeiro

7 Non‐Covalent Stabilization in Transition Metal Coordination and Organometallic Complexes 115
Predrag Petrović, Jean‐Pierre Djukic, Andreas Hansen, Christoph Bannwarth, and Stefan Grimme

8 Halogen Bonding in the Synthesis and Design of Coordination and Organometallic Compounds 145
Abel M. Maharramov, Namiq Q. Shixaliyev, Atash V. Gurbanov, Kamran T. Mahmudov, Valentine G. Nenajdenko, Armando J. L. Pombeiro, and Maximilian N. Kopylovich

9 The Influence of Non‐Covalent Interactions in the Structure and Dimensionality of Hybrid Compounds and Coordination Polymers 163
Ferdinando Costantino, Andrea Ienco, and Marco Taddei

Part III Crystal Design and Host–Guest COMPOUNDS 185

10 Dihalogens as Halogen Bond Donors 187
Matti Haukka, Pipsa Hirva, and Kari Rissanen

11 Construction of Supramolecular Assemblies Based on Anion–π Interactions 199
Antonio Bauzá and Antonio Frontera

12 A symmetric Azamacrocycles as Chiral Solvating Agents 213
Koichi Tanaka

13 New Strategies for the Design of Inclusion Compounds with Cucurbituril Hosts 229
Na’il Saleh

14 Parallel Interactions of Aromatic Molecules at Large Horizontal Displacements 241
Dušan P. Malenov and Snežana D. Zarić

15 Selective Molecular Binding and Nanosupramolecular Assembly of p‐Sulfonatocalix[n]arenes 261
Yu Liu and Yi‐Xuan Wang

16 Synthesis, Design, Characterization, and Application of Metallo‐Supramolecular Polymers 283
Lipeng He and Weifeng Bu

Part IV Catalysis 313

17 Catalytic Applications of Metal Complexes Immobilized by Non‐Covalent Interactions onto Chemically Derived Graphenes and Related Materials 315
Sara Sabater and Jose A. Mata

18 Cooperation of Non‐Covalent Interactions and Coordination in Catalysis 327
Abel M. Maharramov, Kamran T. Mahmudov, Maximilian N. Kopylovich, Rafiga A. Aliyeva, and Armando J. L. Pombeiro

19 Hybrid Ordered Mesoporous Materials as Supports for Permanent Enzyme Immobilization Through Non‐Covalent Interactions 345
Victoria Gascón, Carlos Márquez‐Alvarez, Isabel Díaz, and Rosa M. Blanco

Part V Biorelevant Syntheses 361

20 Modulation of Biorelevant Radical Reactions by Non‐Covalent Interactions 363
Riccardo Amorati and Luca Valgimigli

21 Current Understanding of π–π Interactions and the Applications in Protein Design 381
Jianmin Gao and Azade S. Hosseini

22 Non‐Covalent Interactions for the Preparation of Pseudopeptidic Synthetic Compounds and Materials 391
Jordi Solà and Ignacio Alfonso

Part VI Material Chemistry 413

23 Non‐Covalent Exfoliation of Graphite to Produce Graphene 415
Yingkui Yang, Dean Shi, and Tao Jiang

24 Electrostatic Interactions in the Design of Polymeric Products 431
Lorenzo M. Polgar and Francesco Picchioni

25 S upramolecular Steric Hindrance at Bulky Organic/Polymer Semiconductors and Devices 443
Ling‐Hai Xie and Wei Huang

Index 457

"As a whole, the book succeeds in bringing together aspects of non-covalent interactions from organic, inorganic and materials chemistry perspectives. Personal highlights include: comprehensive reviews by Pombeiro on interaction-mediated activation of covalent bonds; sections on halogen bonding by Kopylovich, Pomebeiro and Rissanen; anion-pi interactions by Frontera; the synthesis of coordination polymers by Taddei and Bu; and the self-assembly and synthesis of peptidomimetics by Solà and Alfonso...In summary, if you are looking for a book that covers many aspects of non-covalent interactions and how this relates to chemical and materials synthesis from a breadth of different perspectives, then this book would certainly be a good starting point to both inform and educate." (AOC 11/04/2017)