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