The Author
Prof. Dr. Robert Glaser
Ben-Gurion University of the Negev
Department of Chemistry
84105 Beer-Sheva
Israel
About the companion website
This book is accompanied by a companion website:
3D animations showing most of the molecules contained in this book can be found under www.wiley.com/go/Glaser/Symmetry
All books published by Wiley-VCH are carefully produced. Nevertheless, authors, editors, and publisher do not warrant the information contained in these books, including this book, to be free of errors. Readers are advised to keep in mind that statements, data, illustrations, procedural details or other items may inadvertently be inaccurate.
Library of Congress Card No.: applied for
British Library Cataloguing-in-Publication Data
A catalogue record for this book is available from the British Library.
Bibliographic information published by the Deutsche Nationalbibliothek
The Deutsche Nationalbibliothek lists this publication in the Deutsche Nationalbibliografie; detailed bibliographic data are available on the Internet at <http://dnb.d-nb.de>.
© 2015 Wiley-VCH Verlag GmbH & Co. KGaA, Boschstr. 12, 69469 Weinheim, Germany
All rights reserved (including those of translation into other languages). No part of this book may be reproduced in any form – by photoprinting, microfilm, or any other means – nor transmitted or translated into a machine language without written permission from the publishers. Registered names, trademarks, etc. used in this book, even when not specifically marked as such, are not to be considered unprotected by law.
Print ISBN: 978-3-527-33749-1
ePDF ISBN: 978-3-527-68420-5
ePub ISBN: 978-3-527-68421-2
Mobi ISBN: 978-3-527-68414-4
oBook ISBN: 978-3-527-68419-9
Cover Design Formgeber, Mannheim, Germany
Printing and Binding Markono Print Media Pte Ltd, Singapore
To Darling Yael: a woman of valor (Eshet Hayil).
This book is the outgrowth of a graduate-level “Special Topics in Structural chemistry and Symmetry Course” taught concurrently in Hebrew at Ben-Gurion University of the Negev, Beer-Sheva, and in English at the Feinberg Graduate School, Weizmann Institute of Science, Rehovot, Israel. One educational goal of the course was to expose the participants to a path toward stereochemical knowledge different than the one ordinarily presented in standard organic stereochemistry lectures. In recent years, this course has become part of the advanced undergraduate curriculum of the Cross-Border Program in Biological Chemistry administered by the Johannes Kepler Universität Linz and the Jihočeská Univerzita v Českých Budějovicích, (University of South Bohemia, Budweis, Czech Republic) – two neighboring universities on either side of a common, and now peaceful, international frontier. It is hoped that similar binational programs integrating students in a common goal toward mutual cultural exchange and tolerance through advanced science education will one day be the norm between my own country and its Arab neighbors. Over the past three decades, this course has been given, in whole or in part, around the world (Australasia: Uni. Wollongong AU; Uni. Auckland NZ; Massey Uni., NZ; Uni. Kyoto JP; Uni. Mandalay, Myanmar MM; Europe: Uni. Twente NL; Uni. Zagreb HR; Serbian Acad. Sci., Belgrade RS; Boğaziçi Uni., Istanbul TR; and the Americas: UCLA; Uni. Syracuse; Nacional Autonom. Univ. Mexico MX; CINVESTAV – Nacional Polytech. Inst. Mexico MX; Uni. Nacional Costa Rica CR; Uni. Fed. Rio de Janeiro BR; Fluminense Fed. Uni. BR; Uni. National Córdoba AR; and Uni. Nacional Tucumán AR).
One important secondary goal of this book is to demonstrate a common interface between the aesthetic world of form and that of structural chemistry. Structural chemistry is unfortunately often not understood at the time of important career-making decisions in secondary school. Many labor under the misconception that chemistry is a daily regimen of titrations and/or balancing redox equations. Another objective was to stress the intimate impact of environment upon a molecule's conformation and structure: change the first and the other is not invariant. In a limited-size book, such as this, the various subjects that can be discussed can obviously not be comprehensive. They were chosen to be a limited sampling of those that exhibited basic principles and provided vehicles for the exposition of stereochemistry.
Without the patience, encouragement, and understanding of Yael Burko-Glaser, my dear wife and life partner of 53 wonderful years, this dream of writing a book could not have come to pass. To my immediate family: daughter Yardenna, son Gil, daughter-in-law Adva Almog-Glaser, grandsons Ron Zeev, Tal David, and granddaughters Or and Hadar, now an IDF commander, it is my hope that intellectual and scientific endeavor will make their world a better and more peaceful place than it was at their birth. To them all, this book is dedicated.
Finally, it is both fit and proper to remember the teachers who shaped our minds and events that changed our lives. George Noyes was my inspiring 1958 11th grade chemistry teacher at Great Neck North Senior High School (Long Island, NY) who enthralled his class with the wonders of chemistry and also told us of the introduction of electric light in his boyhood home. Madeleine M. Joullié (University of Pennsylvania, Philadelphia), my undergraduate professor, showed us the world of functional group organic chemistry. Upon graduation in 1964, I was employed as a Development Chemist at PPG Industries, Structural Adhesives Division, Bloomfield, NJ. The PPG Employee Education Program rejected my enrollment in the New York University Graduate School of Business Administration, despite my already approved admission. Instead, they encouraged me to upgrade my Penn Chemistry B.A. into a full B.Sc. degree and then undertake part-time evening M.Sc. studies at the Polytechnic Institute of Brooklyn (a center of excellence in polymer chemistry). Dr Lincoln Hawkins next affected my life by informing me that acceptance of the Bell Laboratories (Murray Hill, NJ) job offer, having only the M.Sc. Chemistry degree, meant that I could not reach the highest echelons of their Scientific Staff. This provided the impetus to return to full-time studies. The Soviet Union Space Exploration program's Sputnik success prompted the United States Congress to pass the National Defense Education Act (NDEA). This provided me, and others, with predoctoral fellowships in the physical sciences. While at Rutgers University School of Graduate Studies, the scientific acumen of Donald J. Cram and George S. Hammond, in their revolutionary text “Organic Chemistry,” Second Edition, McGraw-Hill: New York, 1959, did more than anything else to reveal that there was a wonderful logical chemical-intermediate-based foundation to organic chemistry rather than reliance on rote memory. The provisions of a 2-year US National Institutes of Health Postdoctoral Fellowship did not permit its use abroad, despite my prior arrangements with the Israeli biophysicist Ephraim Katchalski-Katzir to be a postdoctoral research associate at the Weizmann Institute of Science, Rehovot. In 1971, Prof. Katzir, who later became the fourth President of Israel, encouraged me not to take his job offer at WIS, but rather to start out at the new University of the Negev and to have the pleasure (“nachas” in Yiddish) of building, designing, and molding the nascent Beer-Sheva Department of Chemistry. This is not the time, nor the place, to go into the reasons for immigration to the Jewish State in 1971. Suffice it to say, the feared destruction of the Jewish people in Israel prior to the Six Day War did not come to pass. However, those tension-filled prewar days brought about a radical change of mind and heart, and I then desired to do something for my people, and for myself, rather than continue a comfortable existence in the United States of America, the land of my birth.
Special mention must be given to my very talented and inspiring scientific mentors/advisors. First and foremost, the late Edmond J. Gabbay (Rutgers University, Chemistry Department), my PhD mentor and friend, who opened the door to the intriguing world of nucleic acid/diammonium ion interactions. I remember coming home after my first meeting with him, bubbling over with excitement about the “scientific” research project that was proposed to me (after having performed routine polymer chemistry development work at PPG Industries for 3 years). At Princeton, I owe my thanks to Paul von Rague Schleyer, who introduced me to the exciting and aesthetic world of adamantane chemistry. The second year of my NIH-funded postdoctoral studies was in X-ray crystallography with Robert Langridge at the Biochemical Sciences Department.
I have left the most significant for last: a 1978 sabbatical with Kurt Mislow back in Princeton probably had more impact upon my scientific development than any other single year in my career. I remember a conversation with K.M. in his office to this very day. He said “Robert, you are working in asymmetric hydrogenation where the rate determining transition-state is ephemeral. There is so much to be learned from ground-state stereochemistry, where at least you know what the structures are.” It was sage advice from a learned scholar. It is thus both an honor and a pleasure to also dedicate this book to all my teachers. Finally, throughout the years, I have had the honor to tutor many research students. Without their sense of inquiry, determination, hard effort, and thirst for knowledge, this book could not have been written.
Much have I learned from my teachers … but even more from my students
Talmud Bavli, Ta'anit 7a'
Robert Glaser
Omer (Negev), Israel, February 2015