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,-,-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.

Abel M. Maharramov graduated in chemistry from the Baku State University, Azerbaijan, in 1971. He obtained his Ph.D. and Habilitation from the Moscow State University and Baku State University in 1976 and 1991, respectively. Since 1991, he is a Full Professor at the Baku State University; now he is the Rector of this University. He is Full Member of the National Academy of Sciences of Azerbaijan. He authored 71 books, (co-)authored 485 research publications, 53 patents, and presented 45 invited lectures at international conferences. His research group focuses on organic, coordination and supramolecular chemistry and in particular on the development of non-covalent interactions in the synthesis, catalysis and crystal engineering. Among his many honors are the ISESCO Prize on Science and Technology (2012, Rabat, Morocco) and honor membership of the National Academy of Sciences of Georgia (2013, Tbilisi, Georgia).

Kamran T. Mahmudov has obtained his B.Sc. (2001), M.Sc. (2003) as well as Ph.D. (2007) and Habilitation (2012) degrees at the Baku State University, where he worked as an Assistant Professor (2006-2008). Then he stared to work as a Post-Doctoral Fellow (2009-now) at the Centro de Química Estrutural, Instituto Superior Técnico. His publication record contains more than 65 peer-reviewed publications in ISI journals, 2 chapters in books and 2 reviews. His main research interest is activation of covalent bonds by cooperation of coordination and non-covalent interactions (mainly hydrogen and halogen bonding), and homogeneous catalysis.

Maximilian N. Kopylovich graduated with distinction in Chemical Engineering (1993) from Byelorussian State Technological University and completed his PhD degree in Chemistry with excellent mark (1998) at the same Institution. Then MK worked as an Assistant Professor at the Byelorussian State Technological University (1998-1999), and then as a Post-Doctoral Fellow (2000-2007), Auxiliary (2008-2013) and Senior (2014-Now) Researcher at the Centro de Química Estrutural, Instituto Superior Técnico (IST), Portugal. His publication record contains more than 140 peer-reviewed publications, including ca. 120 research papers in ISI journals (>1700 citations, average citations per item 14.46; h=23, see below), 11 patents, about 80 conference presentations. Scientific interests of MK lay mainly within Inorganic (Coordination) Chemistry. In particular, he participated in the development of new methods of synthesis of triazapentadienato-, aminopolyalcoholato-, arylhydrazo-, iminoisoindolinone, tetrazolato-, pentane-2,4-dione-, piperazine-, 1,3,5-triaza-7-phosphaadamantane (PTA), etc. complexes of metals from virtually all groups of the Periodic Table. Current research interests of MK are related to the metal-mediated (template) and hydrogen(halogen)-assited syntheses of new coordination compounds and supramolecular assemblies.

Armando J. L. Pombeiro is Full Professor at the Instituto Superior Técnico in Lisbon (Portugal), Full Member of the Academy of Sciences of Lisbon (in charge of various directive and representative positions) and President of the Portuguese Electrochemical Society. His research group investigates the activation of small molecules with industrial, environmental or biological significance, including metal-mediated synthesis and catalysis (e.g., functionalization of alkanes under mild conditions), crystal engineering of coordination compounds, design and self-assembly of polynuclear and supramolecular structures, molecular electrochemistry and theoretical studies. He was Chairman of the 25th ICOMC and member of organizing/scientific committees of 40 international conferences or schools. He authored one book (plus three as editor), (co-)authored 600 research publications, 33 patents, and presented 90 invited lectures at international conferences. His work has received ca. 11,800 citations, h-index = 51 (Web of Science). Among his many honors, Dr. Pombeiro has been awarded the Madinabeitia-Lourenço Prize from the Spanish Royal Chemical Society.

Notes on Editors ix

List of Contributors xi

Preface xv

Part I Organic Synthesis 1

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

2 BoronNitrogen 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 Phenylethylamines with Nonenolizable Aldehydes 49
Rodolfo Quevedo

4 NonCovalent Interactions in the Synthesis of Macrocycles 63
Evgeny A. Kataev

Part II Inorganic, Coordination and Organometallic Syntheses 83

5 NonCovalent Interactions of Water with Metal Complexes in Solution 85
Antonio Romerosa and Franco Scalambra

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

7 NonCovalent Stabilization in Transition Metal Coordination and Organometallic Complexes 115
Predrag Petrovi, JeanPierre 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 NonCovalent 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 HostGuest COMPOUNDS 185

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

11 Construction of Supramolecular Assemblies Based on Anion 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
Nail Saleh

14 Parallel Interactions of Aromatic Molecules at Large Horizontal Displacements 241
Du¨an P. Malenov and Sne?ana D. Zari

15 Selective Molecular Binding and Nanosupramolecular Assembly of pSulfonatocalix[n]arenes 261
Yu Liu and YiXuan Wang

16 Synthesis, Design, Characterization, and Application of MetalloSupramolecular Polymers 283
Lipeng He and Weifeng Bu

Part IV Catalysis 313

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

18 Cooperation of NonCovalent 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 NonCovalent Interactions 345
Victoria Gascón, Carlos MárquezAlvarez, Isabel Díaz, and Rosa M. Blanco

Part V Biorelevant Syntheses 361

20 Modulation of Biorelevant Radical Reactions by NonCovalent Interactions 363
Riccardo Amorati and Luca Valgimigli

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

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

Part VI Material Chemistry 413

23 NonCovalent 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
LingHai Xie and Wei Huang

Index 457