Lindstrom - Organic Reactions in Water (Blackwell, 2007).pdf

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Organic Reactions in Water
Organic Reactions in Water
Principles, Strategies and Applications
Edited by
U. Marcus Lindstrom
¨
Assistant Professor
Department of Chemistry
McGill University
C
2007 by Blackwell Publishing
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the UK Copyright, Designs and Patents Act 1988, without the prior permission of the publisher.
First published 2007 by Blackwell Publishing Ltd
ISBN: 978-1-4051-3890-1
Library of Congress Cataloging-in-Publication Data
Organic reactions in water:principles, strategies and applications / edited by U. Marcus Lindstr¨ m.
o
p. cm.
Includes bibliographical references and index.
ISBN-13: 978-1-4051-3890-1 (hardback:alk. paper)
ISBN-10: 1-4051-3890-4 (hardback:alk. paper)
1. Water chemistry. 2. Solvents–Environmental aspects. 3. Organic compounds–Synthesis–
Environmental aspects. I. Lindstr¨ m, U. Marcus
o
QD 169.W3O74 2007
547 .2–dc22
2006022512
A catalogue record for this title is available from the British Library
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Contents
Contributors
Preface
Foreword
1 A Fifty-Year Perspective on Chemistry in Water
RONALD BRESLOW
1.1 Enzyme mimics and models
1.1.1 Thiamine
1.1.2 Cyclodextrins
1.1.3 Cyclodextrins with bound metal ions
1.1.4 Cyclodextrin dimers
1.1.5 Ribonuclease mimics
1.1.6 Transaminase mimics
1.1.7 Cytochrome P-450 mimics
1.2 Reactions in water promoted by hydrophobic binding
of small molecules
1.2.1 Diels–Alder reactions
1.2.2 The benzoin condensation
1.2.3 Atom transfer reactions
1.3 Quantitative antihydrophobic effects in water
and the geometries of transition states
1.4 The importance of water as a reaction solvent
References
2 Structure and Properties of Water
JAN B.F.N. ENGBERTS
2.1 Water, the molecule and the liquid
2.1.1 The single water molecule
2.1.2 Liquid water
2.2 Properties of water
2.2.1 Solvent properties and parameters
2.2.2 Thermodynamics of hydration
2.2.3 Hydrophobic interactions
2.3 Kinetic solvent effects in aqueous solution
References
3 Acid Catalysis in Water
¯
CHIKAKO OGAWA AND SHU KOBAYASHI
3.1 Homogeneous catalysis
3.1.1 Brønsted acid catalysis
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