The Importance of Pi-Interactions in Crystal Engineering: Frontiers in Crystal Engineering / Edition 2

The Importance of Pi-Interactions in Crystal Engineering: Frontiers in Crystal Engineering / Edition 2

ISBN-10:
0470688270
ISBN-13:
9780470688274
Pub. Date:
04/17/2012
Publisher:
Wiley

Hardcover

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Overview

The Importance of Pi-Interactions in Crystal Engineering: Frontiers in Crystal Engineering / Edition 2

Crystal engineers aim to control the way molecules aggregate in thecrystalline phase and are therefore concerned with crystalstructure prediction, polymorphism, and discovering the relativeimportance of different types of intermolecular forces and theirinfluence on molecular structure. In order to design crystalstructures, knowledge of the types, strengths, and nature ofpossible intermolecular interactions is essential. Non-covalentinteractions involving p-systems is a theme that is under extensiveinvestigation as these interactions can be inductors for theassembly of a vast array of supramolecular architectures.

The Importance of Pi-Interactions in CrystalEngineeringcovers topics ranging from the identification ofinteractions involving p-systems, their impact on molecular andcrystal structure in both organic and metallorganic systems, andhow these interactions might be exploited in the design of newmaterials. Specialist reviews are written by internationallyrecognized researchers drawn from both academia and industry.

The Importance of Pi-Interactions in CrystalEngineeringprovides an essential overview of this importantaspect of crystal engineering for both entrants to the field aswell as established practitioners, and for those working incrystallography, medicinal and pharmaceutical sciences, solid-statechemistry, physical chemistry, materials and nanotechnology

Product Details

ISBN-13: 9780470688274
Publisher: Wiley
Publication date: 04/17/2012
Pages: 392
Product dimensions: 6.70(w) x 9.90(h) x 0.90(d)

Table of Contents

Preface xiii

List of Contributors xv

1 The CH/π Hydrogen Bond: Implication in CrystalEngineering 1
Motohiro Nishio, Yoji Umezawa, Hiroko Suezawa and SeiTsuboyama

1.1 Introduction 1

1.2 Cooperative Effect of the CH/π Hydrogen Bond7

1.3 CH/π Hydrogen Bonds in Supramolecular Chemistry14

1.4 Crystallographic Database Analyses 25

1.5 Systematic CSD Analyses of the CH/π HydrogenBond 28

1.6 Summary and Outlook 31

2 New Aspects of Aromatic π. . . π and C-H. . . π Interactions in Crystal Engineering 41
Roger Bishop

2.1 Introduction 41

2.2 Three-Dimensional Aromatic Structures 44

2.3 Endo,Endo-Facial Dimers 46

2.4 Multiply Halogenated Heteroaromatic Molecules 49

2.5 Expansion of the Endo,Endo-Facial Dimer 56

2.6 (EF)6 Brick-Like Building Blocks 59

2.7 Other Novel Multiple Edge–Face Assemblies 64

2.8 Other Types of Aryl–Aryl Contacts 68

2.9 Conclusions 75

3 CH. . .π and π. . .πInteractions as Contributors to the Guest Binding in ReversibleInclusion and Encapsulation Complexes 79
Dr. Pablo Ballester and Dr. Shannon M. Biros

3.1 Introduction 79

3.2 Probing Aromatic–Aromatic(ππ) Interactions andCH–π Interactions with Solid-State Structures ofReversible Inclusion and Encapsulation Complexes 83

3.2.1 Inclusion Complexes 83

3.3 Summary and Outlook 104

4 A Rudimentary Method for Classification ofπ···π Packing Motifs forAromatic Molecules 109
Leigh Loots and Leonard J. Barbour

4.1 Introduction 109

4.2 Theoretical Models 110

4.3 π···π Interactions111

4.4 Structure Prediction and Comparisons 113

4.5 π···π Interactions inHeteroaromatic Molecules 113

4.6 π···π Interactions inCocrystals 119

4.7 Summary 123

5 Conformational Flexibility and Selectivity inHost–Guest Systems 125
Nikoletta B. Bathori and Luigi R. Nassimbeni

5.1 Introduction 125

5.2 Selectivity 129

5.3 Concluding Remarks 139

6 Organic π-Radicals in the Solid-State: fromLocalised to Delocalised σ-Bonding 143
Marc Fourmigue

6.1 Introduction 143

6.2 Molecules for π-Radical Formation 144

6.3 Dimers of Radicals versus Radical Dimers (Pimers) 149

6.4 Solid-State Magnetic and Conducting Properties 154

6.5 Conclusions 159

7 Arene–Perfluoroarene Interactions in CoordinationArchitectures 163
Akiko Hori

7.1 Introduction 163

7.2 Background 165

7.3 Guest Recognition by Coordination Networks 169

7.4 Fluorinated Coordination Complexes 172

7.5 Cocrystals of Coordination Complexes 179

7.6 Self-Assembly in Solution 181

7.7 Conclusions 182

8 Halogen. . .π Interactions as ImportantContributors to Binding Affinity in Medicinal Chemistry 187
Hans Matter, Marc Nazare, and Stefan Gussregen

8.1 Introduction 187

8.2 General Aspects of Halogen Atoms in Medicinal Chemistry189

8.3 Fluorine: a Unique Halogen Atom 190

8.4 Interactions of Higher Halogen Atoms 196

8.5 Interactions of Higher Halogen Atoms to Aromatic Rings204

8.6 Conclusions 226

9 Fuzzy Electron-Density Fragments as Building Blocks inCrystal-Engineering Design 233
Paul G. Mezey

9.1 Introduction 233

9.2 A Brief Review of a Fuzzy Electron-Density FragmentationScheme Suitable for Molecular Design 235

9.3 The Low-Density "Glue" Range of Globular Macromolecules,Functional Groups, and the Role of π-Interactions inFuzzy Fragment Selection 238

9.4 Summary 239

10 Noncovalent Interactions of π-systems inCrystal Structures of Transition-Metal Complexes 243
Goran V. Janjic and Snezana D. Zaric

10.1 Introduction 243

10.2 Interactions with Organic π-Systems 244

10.3 Interactions with π-Systems of Chelate Rings254

11 Intermolecular C–H · · ·π(Chelate) Interactions – Prevalence in theCrystal Structures of Metal 1,1-Dithiolates 275
Julio Zukerman-Schpector and Edward R.T. Tiekink

11.1 Introduction 275

11.2 Methodology and Preliminary Survey 277

11.3 Supramolecular Architectures Based on C–H·· ·π Interactions 280

11.4 Discussion and Conclusions 295

12 Supramolecular Aggregation Patterns and StereochemicalConsequences of Tellurium(Lone Pair)· ··π(Aryl) Interactions 301
Ionel Haiduc, Edward R.T. Tiekink and JulioZukerman-Schpector

12.1 Introduction 301

12.2 Methodology 302

12.3 Results 303

12.4 The Influence of Te(Lone Pair)· ··π(Aryl) Synthons Upon Coordination Geometry318

12.5 Summary and Conclusions 319

13 Supramolecular Assembly of Silver(I) Complexes withArgentophilic and Silver. . .Carbon Interactions 323
Thomas C. W. Mak, Liang Zhao and Xiao-Li Zhao

13.1 Introduction 323

13.2 Silver Double/Multiple Salts Containing Ag2C2 326

13.3 Supramolecular Assembly of Silver(I) Double/Triple Saltswith Potentially Exo-Bidentate Ligands 332

13.4 Silver(I) Multiple Salts of 1,3-Butadiynediide(C42−) 337

13.5 Supramolecular Assembly with Silver tert-Butylethynide338

13.6 Double/Multiple Salts of Silver Arylethynides 342

13.7 Assembly of Silver–Heteroaromatic EthynideSupramolecular Synthons R-C=C Agn (n = 4, 5) (R =Thienyl, Pyridyl, Pyrazinyl, Pyrimidyl) 346

13.8 Assembly of Silver–Ethynide Supramolecular SynthonAssisted by Silver. . .Aromatic Interaction 350

13.9 Assembly of Silver–Ethynide Supramolecular SynthonAssisted by Intermolecular Silver. . .Halogen Interaction352

13.10 Coordination Networks Constructed of MultinuclearC2@Agn Aggregates and Polyoxometalate Species 353

13.11 Supramolecular Assembly of Large Silver–EthynideClusters 355

13.12 Conclusion and Outlook 363

Acknowledgments 363

References 364

Index 367

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