Research Catalog

Title

The weak hydrogen bond : in structural chemistry and biology / Gautam R. Desiraju and Thomas Steiner.

Author

Desiraju, G. R. (Gautam R.)

Publication

Oxford ; New York : Oxford University Press, 1999.

Items in the Library & Off-site

Details

Additional Authors

Steiner, Thomas.

Description

xiv, 507 p. : ill.; 25 cm.

Summary

The existence of the weak hydrogen bond has been postulated for some years, but only recently has it become evident that the bond plays a distinctive role in the characteristics of certain molecules. This book provides a critical assessment.

Series Statement

International Union of Crystallography monographs on crystallography ; 9

Uniform Title

International Union of Crystallography monographs on crystallography ; 9.

Subject

• Hydrogen bonding
• hydrogen bonding
• Wasserstoffbrückenbindung
• Waterstofbruggen
• Supramoleculaire systemen
• Biomoleculen
• Spectrometrie
• Kristalstructuur
• HYDROGEN BONDS
• MOLECULAR STRUCTURE
• CHEMISTRY
• BIOLOGY
• ORGANOMETALLIC COMPOUNDS
• CRYSTALLOGRAPHY
• Structure cristalline (solides)
• Chimie supramoléculaire
• Liaisons hydrogène
• Wasserstoffbru?ckenbindung

Bibliography (note)

• Includes bibliographical references (p. [447]-499) and index.

Contents

1.1 The hydrogen bond 1 -- 1.1.1 Historical background 1 -- 1.1.2 Geometrical parameters and definitions 5 -- 1.1.3 Energetic parameters and definitions 9 -- 1.2 The weak or non-conventional hydrogen bond -- scope of this work 11 -- 1.2.1 Classification of hydrogen bonds 12 -- 1.2.2 The nature of the hydrogen bond interaction and its limits 16 -- 1.2.3 Differences between strong and weak hydrogen bonds 19 -- 1.3 Methods of studying weak hydrogen bonds 21 -- 1.3.1 Crystal structure analysis and statistical treatment of these results 21 -- 1.3.2 Vibrational spectroscopy 26 -- 1.3.3 Gas-phase rotational spectroscopy 27 -- 1.3.4 Computation 27 -- 2 Archetypes of the weak hydrogen bond -- C -- H ... O and C -- H ... N interactions in organic and organometallic systems 29 -- 2.1 Historical developments 29 -- 2.1.1 Sutor's study 32 -- 2.1.2 The dark ages 35 -- 2.1.3 The Taylor-Kennard paper 38 -- 2.2 General properties 40 -- 2.2.1 Vibrational spectroscopy 40 -- 2.2.2 Length properties 44 -- 2.2.3 Angular properties 58 -- 2.2.4 C -- H bond lengthening 68 -- 2.2.5 Reduction of thermal vibrations 70 -- 2.2.6 Computational studies and hydrogen bond energies 73 -- 2.2.7 Cooperativity 80 -- 2.2.8 Hardness and softness 86 -- 2.2.9 Intramolecular phenomena 89 -- 2.2.10 Influence on crystal packing 97 -- 2.2.11 Repulsive and destabilizing C -- H ... O contacts 108 -- 2.2.12 Weak hydrogen bonds in liquids and solution 116 -- 2.2.13 Recapitulation 120 -- 3 Other weak and non-conventional hydrogen bonds 122 -- 3.1 [pi]-Acceptors 122 -- 3.1.1 What is a [pi]-acceptor? 122 -- 3.1.2 Solution and gas phase experiments 124 -- 3.1.3 Phenyl groups 130 -- 3.1.4 Alkynes 164 -- 3.1.5 Alkenes 185 -- 3.1.6 Heterocycles 190 -- 3.1.7 Other [pi]-acceptors 193 -- 3.2 Weak atomic acceptors 202 -- 3.2.1 Group VII elements -- covalent halogen 202 -- 3.2.2 Group VI elements -- S, Se and Te 224 -- 3.2.3 Group V elements -- P, As and Sb 238 -- 3.2.4 Group IV elements -- isonitriles, carbanions, carbenes and silylenes 242 -- 3.3 Halide anions 246 -- 3.4 Weak donors 253 -- 3.4.1 S -- H 253 -- 3.4.2 P -- H and P[superscript +] -- H 267 -- 3.4.3 Se -- H, As -- H and Si -- H 269 -- 3.5 Organometallics 270 -- 3.5.1 Metal atoms as acceptors -- X -- H ... M hydrogen bonds 271 -- 3.5.2 Metal atom groups as donors -- M -- H ... A hydrogen bonds 277 -- 3.5.3 Agostic interactions -- M ... (H -- C) 280 -- 3.6 Other varieties 281 -- 3.6.1 The dihydrogen bond -- X -- H ... H -- M 283 -- 3.6.2 The inverse hydrogen bond -- X -- H[superscript -] ... A[superscript +] 291 -- 4 The weak hydrogen bond in supramolecular chemistry 293 -- 4.1 The solid state -- influence of weak hydrogen bonds on packing 294 -- 4.1.1 The crystal as a supermolecule 294 -- 4.1.2 Crystal structures wherein weak hydrogen bonds are important 296 -- 4.2 Inclusion complexes 303 -- 4.2.1 Crown ethers 303 -- 4.2.2 Oligoaryl hosts 310 -- 4.2.3 Cyclodextrins (cycloamyloses) 311 -- 4.3 Crystal engineering -- promises and problems 315 -- 4.3.1 From molecular to crystal structure 316 -- 4.3.2 The computational approach 321 -- 4.3.3 The experimental approach -- database research 322 -- 4.3.4 Crystal engineering in practice -- supramolecular synthons 323 -- 4.4 Recognition in solution and related phenomena 336 -- 4.4.1 Supramolecular assistance to molecular synthesis 337 -- 4.4.2 Drug design and biological recognition 338 -- 5 The weak hydrogen bond in biological structures 343 -- 5.1.1 Biological structures are not time-stable 344 -- 5.1.2 The crystallographic resolution problem 345 -- 5.2 Peptides and proteins 346 -- 5.2.1 The building blocks -- amino acids 346 -- 5.2.2 C -- H ... O hydrogen bonds 350 -- 5.2.3 X -- H ... [pi] hydrogen bonds 363 -- 5.2.4 Protein-ligand interactions 376 -- 5.2.5 Enzymatic activity 381 -- 5.3 Nucleic acids 385 -- 5.3.1 Nucleic acid constituents 389 -- 5.3.2 Polymeric DNA and RNA 393 -- 5.4 Carbohydrates 407 -- 5.4.1 Chemical constitution 407 -- 5.4.2 Hydrogen bond geometry 408 -- 5.4.3 Functionally important C -- H ... O hydrogen bonds 410 -- 5.5 Water molecules 412 -- 5.5.1 Organic hydrates 414 -- 5.5.2 Are there water molecules with vacant hydrogen bond potentials? 426 -- 5.5.3 Macromolecular structures 427.

ISBN

• 0198502524
• 9780198502524

LCCN

99020408

OCLC

• ocm40964761
• 40964761
• SCSB-1033834

Owning Institutions

Princeton University Library