Aromatic interactions : frontiers in knowledge and application / edited by Darren W. Johnson, University of Oregon, Eugene, Oregon, USA, Fraser Hof, University of Victoria, Victoria, British Columbia, Canada.

Format:

Book

Contributor:

Johnson, Darren W. (Darren William), editor.

Hof, Fraser, editor.

Series:

Monographs in supramolecular chemistry ; 1368-8642 no. 20.

Monographs in supramolecular chemistry, 1368-8642 ; 20

Language:

English

Subjects (All):

Supramolecular chemistry.

Aromatic compounds.

Physical Description:

xiv, 282 pages : illustrations (chiefly color) ; 24 cm.

Other Title:

Frontiers in knowledge and application

Place of Publication:

Cambridge : The Royal Society of Chemistry, [2017]

Summary:

The field of aromatic interactions, the fundamental nature of substituent effects and the identification of contacts between anions and aromatic systems have generated stimulating arguments in recent years. New theoretical frameworks have been developed and tested and aromatic interactions have emerged as potential solutions for varied problems in biology and materials science. This book provides a wide ranging survey of the latest findings and advances surrounding aromatic interactions, stretching from the fundamentals to modern applications in synthesis, biology and materials chemistry. It also discusses computational, experimental and analytical approaches to understanding these interactions, including φ-φ, anion-φ, and cation-φ interactions. Aromatic Interactions- Frontiers in Knowledge and Application is a useful text for advanced students and researchers, and appeals to those working within the fields of supramolecular chemistry, computational chemistry and thermodynamics. Book jacket.

Contents:

Chapter 1 Modern Computational Approaches to Understanding Interactions of Aromatics / Michael Lewis Lewis, Michael, Christina Bagwill Bagwill, Christina, Laura Hardebeck Hardebeck, Laura, Selina Wireduaah Wireduaah, Selina 1

1.1 Introduction and Background 1

1.1.1 Arene-Arene Interactions 2

1.1.2 Cation-Arene Interactions 3

1.1.3 Beyond the Aromatic Quadrupole Moment 4

1.2 Computational Approaches to Understanding Arene-Arene Interactions 5

1.2.1 The Nature of Arene-Arene Interactions 5

1.2.2 Predicting the Strength of Arene-Arene Interactions 9

1.3 Computational Approaches to Understanding Cation-Arene Interactions 10

1.3.1 The Nature of Cation-Arene Interactions 10

1.3.2 Predicting the Strength of Cation-Arene Interactions 13

1.4 Summary 14

References 15

Chapter 2 Role of Aromatic Interactions in Directing Organic Reactions / Rajat Maji Maji, Rajat, Steven E. Wheeler Wheeler, Steven E. 18

2.1 Introduction and Background 18

2.2 Aromatic Interactions of Relevance to Organic Reactions 19

2.3 Aromatic Interactions in Non-Catalytic Reactions 22

2.4 Aromatic Interactions in Transition-Metal Catalyzed Reactions 24

2.5 Aromatic Interactions in Organocatalysis 25

2.6 Aromatic Interactions in Cooperative Catalysis 31

2.7 Reactions Directed by Anion-π Interactions 31

2.8 Reactions Directed by π-π⁺ Interactions 33

2.9 Concluding Remarks 34

Acknowledgements 34

References 34

Chapter 3 Anion-π Interactions: Theoretical Studies, Supramolecular Chemistry and Catalysis / A. Frontera Frontera, A., P. Ballester Ballester, P. 39

3.1 Introduction 39

3.2 Physical Nature 41

3.3 Anion-π Interactions in Solution 46

3.3.1 Supramolecular Chemistry and Synthetic Receptors Involving Anion-π Interactions 46

3.3.2 Anion-π Interactions in Reaction Catalysis 65

3.3.3 Ionic Liquids 74

3.4 On the Importance of Anion-π Interactions in the Solid State 76

3.4.1 Charge Neutral π-Systems 76

3.4.2 Aromatic Ligands Coordinated to Metal Ions 83

3.4.3 Positively Charged or Protonated Aromatics 86

3.5 Outlook 88

Acknowledgements 88

References 89

Chapter 4 A New Non-Covalent Bonding Mode in Supramolecular Chemistry: Main Group Element Lone-Pair-π(arene) Interactions / Ignez Caracelli Caracelli, Ignez, Ionel Haiduc Haiduc, Ionel, Julio Zukerman-Schpector Zukerman-Schpector, Julio, Edward R. T. Tiekink Tiekink, Edward R. T. 98

4.1 Introduction 98

4.2 Methodology 100

4.3 Overview of M(lp)...π(arene) Interactions 102

4.3.1 Indium(I) 102

4.3.2 Thallium(I) 102

4.3.3 Tin(II) 104

4.3.4 Lead(II) 105

4.3.5 Arsenic(III) 106

4.3.6 Antimony(III) 108

4.3.7 Bismuth(III) 108

4.3.8 Selenium(II, IV) 109

4.3.9 Tellurium(II, IV) 115

4.4 Biological Relevance 116

4.5 Conclusions and Outlook 118

Acknowledgements 119

References 119

Chapter 5 Solution-Phase Measurements of Aromatic Interactions / K. D. Shimizu Shimizu, K. D., R Li Li, R

5.1 Introduction 124

5.2 Types of Model Systems 125

5.2.1 Bimolecular Model Systems 125

5.2.2 Unimolecular Model System 126

5.2.3 Thermodynamic Approach 126

5.2.4 Kinetic Approach 127

5.2.5 Analysis of Experiment Models 127

5.2.6 Isolation of the Interaction Energy 128

5.3 Case Studies of Solution-Phase Measurements of Aromatic Interactions 129

5.3.1 Aromatic Stacking Interactions 129

5.3.2 Aromatic Edge-to-Face Interactions 140

5.3.3 Aliphatic CH-φ Interactions 145

5.3.4 Aromatic Cation-φ Interactions 150

5.3.5 Anion-φ Interaction 155

5.3.6 Lone Pair-φ Interaction 159

5.4 Conclusion 162

Acknowledgements 163

References 163

Chapter 6 Molecular Recognition of Aromatic Peptides and Proteins in Nature and by Design / Andrew T. Bockus Bockus, Andrew T., Adam R. Urbach Urbach, Adam R. 172

6.1 Overview 172

6.2 Aromatic Amino Acids 173

6.3 Aromatic Residues in Biological Complexes 175

6.4 Designed Ligands 180

6.5 Efficiency of Aromatic Residues 182

6.6 Synthetic Receptors 183

6.7 Synthetic Receptors for Amino Acids 184

6.7.1 Aromatic Amino Acid Recognition by Viologen-Containing Receptors 184

6.7.2 Aromatic Amino Acid Recognition by Cyclodextrins 186

6.7.3 Aromatic Amino Acid Recognition by Cucurbiturils 188

6.7.4 Recognition of Non-Aromatic Amino Acids by Synthetic Receptors 189

6.8 Recognition of Aromatic Peptides by Synthetic Receptors 192

6.8.1 Early Receptors for Peptides 193

6.8.2 Peptide Recognition by Coordination Complexes 195

6.8.3 Peptide Recognition by Cucurbit[n]urils 197

6.9 Recognition of Aromatic Sites on Proteins by Synthetic Receptors 203

6.10 Lessons Learned and Challenges 206

Acknowledgements 208

References 208

Chapter 7 Cation-π Interactions in Biomolecular Recognition / Amber L. Koenig Koenig, Amber L., Marcey L. Waters Waters, Marcey L. 214

7.1 The Nature of the Cation-π Interaction 214

7.2 Model Systems for Cation-π Interactions in Aqueous Solution 216

7.2.1 Applications of Synthetic Systems that Mediate Cation-π Interactions 218

7.3 Cation-π Interactions in Proteins 218

7.4 Cation-π Interactions in Nucleic Acids 225

7.5 Cation-π Interactions in Lipids 229

7.6 Conclusions 232

References 232

Chapter 8 Aromatic Molecules on Metallic Surfaces: Structure and Reactivity / Tomas Marangoni Marangoni, Tomas, Ryan R. Cloke Cloke, Ryan R., Felix R. Fischer Fischer, Felix R. 238

8.1 Introduction 238

8.2 Structural Investigations of Aromatic Molecules on Surfaces 240

8.2.1 General Surface Characterization Techniques 240

8.2.2 Visualization Techniques with Sub-Molecular Resolution: STHM and nc-AFM 241

8.3 Reactivity of Aromatic Molecules on Metallic Surfaces 247

8.3.1 Surface-Mediated Polymerization 248

8.3.2 Cyclodehydrogenation Reactions 255

8.3.3 Metal-Coordination Reactions 257

8.3.4 Graphene Nanoribbon Synthesis 261

8.4 Conclusions 269

References 269.

Notes:

Includes bibliographical references and index.

ISBN:

9781782624172

1782624171

OCLC:

952386178