Supramolecular Stereochemistry NATO ASI Series Advanced Science Institutes Series A Series presenting the results of activities sponsored by the NATO Science Committee, which aims at the dissemination of advanced scientific and technological knowledge, with a view to strengthening links between scientific communities. The Series is published by an international board of publishers in conjunction with the NATO Scientific Affairs Division A Life Sciences Plenum Publishing Corporation B Physics London and New York C Mathematical and Physical Sciences Kluwer Academic Publishers D Behavioural and Social Sciences Dordrecht, Boston and London E Applied Sciences F Computer and Systems Sciences Springer-Verlag G Ecological Sciences Berlin, Heidelberg, New York, London, H Cell Biology Paris and Tokyo I Global Environmental Change PARTNERSHIP SUB-SERIES 1. Disarmament Technologies Kluwer Academic Publishers 2. Environment Springer-Verlag / Kluwer Academic Publishers 3. High Technology Kluwer Academic Publishers 4. Science and Technology Policy Kluwer Academic Publishers 5. Computer Networking Kluwer Academic Publishers The Partnership Sub-Series incorporates activities undertaken in collaboration with NATO's Cooperation Partners, the countries of the CIS and Central and Eastern Europe, in Priority Areas of concern to those countries. NATO-PCO-DATA BASE The electronic index to the NATO ASI Series provides full bibliographical references (with keywords and/or abstracts) to more than 50000 contributions from international scientists published in all sections of the NATO ASI Series. Access to the NATO-PCO-DATA BASE is possible in two ways: - via online FILE 128 (NATO-PCO-DATA BASE) hosted by ESRIN, Via Galileo Galilei, I-00044 Frascati, Italy. - via CD-ROM "NATO-PCO-DATA BASE" with user-friendly retrieval software in English, French and German (© WTV GmbH and DATAWARE Technologies Inc. 1989). The CD-ROM can be ordered through any member of the Board of Publishers or through NATO- PCO, Overijse, Belgium. Series C: Mathematical and Physical Sciences - Vol. 473 Supramolecular Stereochemistry edited by Jay S. Siegel Department of Chemistry, University of California, San Diego, California, U.S.A. SPRINGER-SCIENCE+BUSINESS MEDIA, B.V. Proceedings of the NATO Advanced Research Workshop on Supramolecular Stereochemistry Hveragerdi, Iceland September 14-19,1994 A C.I.P. Catalogue record for this book is available from the Library of Congress. ISBN 978-94-010-4157-7 ISBN 978-94-011-0353-4 (eBook) DOI 10.1007/978-94-011-0353-4 Printed on acid-free paper All Rights Reserved © 1995 Springer Science+Business Media Dordrecht Originally published by Kluwer Academic Publishers in 1995 Softcover reprint of the hardcover 1st edition 1995 No part of the material protected by this copyright notice may be reproduced or utilized in any form or by any means, electronic or mechanical, including photo• copying, recording or by any information storage and retrieval system, without written permission from the copyright owner. This book contains the proceedings of a NATO Advanced Research Workshop held within the programme of activities of the NATO Special Programme on Supramolecular Chemistry as part of the activities of the NATO Science Committee. Other books previously published as a result of the activities of the Special Programme are: WIPFF, G. (Ed.), Computational Approaches in Supramolecular Chemistry. (ASIC 426) 1994. ISBN 0-7923-2767-5 FLEISCHAKER, G.R., COLONNA, S. and LUISI, P.L. (Eds.), Self-Production of Supramolecular Structures. From Synthetic Structures to Models of Minimal Living Systems. (ASIC 446) 1994. ISBN 0-7923-3163-X FABBRIZZI, L., POGGI, A. (Eds.), Transition Metals in Supramolecular Chemistry. (ASIC 448) 1994. ISBN 0-7923-3196-6 BECHER, J., SCHAUMBURG, K. (Eds.), Molecular Engineering for Advanced Materials. (ASIC 456) 1995. ISBN 0-7923-3347-0 LA MAR, G.N. (Ed.), Nuclear Magnetic Resonance ofParamagnetic Macromolecules. (ASIC 457) 1995. ISBN 0-7923-3348-9 to my mother in memory ofmyfather Table of Contents Preface Xlll Introduction xv SECTION I: PLENARY CONTRIBUTIONS Macromolecular Stereochemistry: The Differing Roles of a Helix Reversal in Dilute Solution, in a Liquid Crystal, and in a Polymer Blend Mark M. Green* From Molecular to Supramolecular Chirality J.H. Van Esch, N.A.J.M. Sommerdijk, R.J.H. Hajkamp, M.e. Feiters, and R.J.M. Nolte* 3 Template Induced Control of Stereochemistry for the Synthesis of Polymers G. Wulff* 13 Dendrimers - Nanoscopic Supermolecules According to Dendritic Rules and Principles Donald A. Tomalia* 21 Construction of DNA Polyhedra and Knots Through Symmetry Minimization Nadrian e. Seeman*, Yuwen Zhang, Shou Ming Du, and Junghuei Chen 27 Molecular Recognition by Catenated Structures David B. Amabilino*, and J. Fraser Stoddart* 33 Novel Protein Topologies Kurt Mislow*, and Chengzhi Liang 41 A New Molecular Encoding System Steven A. Benner*, Jennifer Horlacher, Johannes Vogel, and Ulrike von Krosigk 47 Recognition of B vs. Z-Form DNA using Nickel and Cobalt Complexes Cynthia J. Burrows*, James G. Muller, Hui-Cheng Shih, and Steven E. Rokita 57 Principles of Antibody Catalysis Donald Hilvert* 63 Mechanistic Studies on the Formation of BZIP·DNA Interfaces. A Simple Example of Supramolecular Stereochemistry David N. Paolella, e. Rodgers Palmer, Steven J. Metallo, and Alanna Schepartz* 83 x Chiral Discrimination in Crystalline Enantiomer Systems: Facts, Interpretations, and Speculations A. Collet*, L. Ziminski, C. Garcia, and F. Vigne-Maeder 91 A Carbohydrate-Carbohydrate Interaction in Water using a Synthetic Model System S. Penades* III Design of Host Molecules Capable of Forming Extremely Stable Host-Guest Complexes Barbara J. Whitlock, and Howard W. Whitlock* 117 Structural Control over the Formation of Calcium Carbonate Mineral Phases in Biomineralization L. Addadi*, J. Aizenberg, S. Albeck, G. Falini, and S. Weiner 127 Hydrogen Bonding Control of Molecular Self-Assembly Ji Yang, Jean-Luc Marendez, Abdullah ZaJar, Steven J. Geib, and Andrew D. Hamilton* 141 Supramolecular Stereochemistry of Supercharged Polycyclic Aromatic Hydrocarbons Lawrence T. Scott* 147 Enhancement of Electrostatic Binding Through Cooperative Interactions: EnthalpylEntropy Compensation and Peptide-Peptide Recognition Mark S. Searle, Martin S. Westwell, Patrick Groves, Gary J. Sharman, and Dudley H. Williams* 151 Toward Columns and Channels from Torands and Molecular Coils Thomas W. Bell*, Aaron M. Heiss, Helene Jousselin, and Richard T. Ludwig 161 SECTION II: POSTER CONTRIBUTIONS QMView: As a Supramolecular Visualization Tool Kim K. Baldridge*, and Jerry P. Greenberg 169 Cis-trans-trans-l,2,3,4-Tetracyclohexylcyclohexane: A Monocyclic Unconstrained Cyclohexane Existing in a Twist-Boat Conformation [shay Columbus, Shmuel Cohen, and Silvio E. Biali* 179 The Conformation of Coumarin-Crown Ethers with Spin-Spin and Site Exchange Simulations (:akl1 Erk* 185 Xl Clathration Properties of Propeller-Shaped Molecules Paolo Finocchiaro* 191 Control of Self-Assembly by Acid-Based Chemistry: Reversible Encapsulation of Xenon by Two Indentical Half-Shells R.M. Grotifeld*, N.R. Branda, C. Valdes, and J. Rebek, Jr. 195 Structural Diversity in a Family of Synthetic Oligoamides Adrian P. Bisson, Fiona J. Carver, Christopher A. Hunter*, Graham S. Lynch, N.J. Osborn, Duncan H. Purvis, Richard J. Shannon, and Kathryn Tse 199 Diastereospecific Recognition of Dyes by Salt Crystals: A Case of Plundered Stereochemistry in Postwar Europe Bart Kahr*, and Michael P. Kelley 203 Selectivity Enhancement by Concave Reagents U. Luning*, and W. Schyja 223 From p-tert-Butyl-Calix[6]arene to p-tert-Butyl-[1 6]metacyclophane. Isolation and Crystal Structure of a Mono Bridged Penta-Phosphoester J.-B. Regnoufde Vains*, R. Lamartine, S. Pellet-Rostaing, M. Perrin, A. Thozet, and S. Lecocq 227 Two Shells About a Nut: Carceplexes, Hemicarceplexes, and Highly Stable Ternary Complexes J.e. Sherman* 233 Cyclodextrin-Metallocene Inclusion Complexes V.I. Sokolov* 239 Dendritic Polyphosphates: Globular Polyelectrolytes? Yitzhak Tor* 247 Author Index 255 Subject Index 257 Preface Organizing this meeting on Supramolecular Stereochemistry has been a fulfilling and eye­ opening adventure. Good fortune reigned through out the process, from the encouragement I received at the outset, to the generous support from NATO and the US National Science Foundation, to the wonderfully positive response that came from the invitees, to the spectacular facilities and surroundings of the conference site in Iceland to the superior proceedings which led to the creation of this book. Supramolecular Stereochemistry is a topic with enormous breadth, such that participants from widely diverse backgrounds could be invited. The conference brought together experts in polymer chemistry, bioorganic chemistry, crystallography, material science, dendrimer science, nanochemistry, conformational analysis, molecular recognition chemistry, and topological stereochemistry. The conference was intensive with 29 lectures and 2 poster sessions in 4 days, but was accented by the beautiful Icelandic environment. The town of Hveragerdi, which hosted the meeting was located in an area 50 KIn east of Reykjavik, and provided an excellent isolated spot with a complete supportive infrastructure which allowed us to be about or work without extraneous worries. It is a special opportunity to be able to document this event with this volume of the NATO-ARW Series. Thanks are due to the publisher for their abundant cooperation in this endeavor.