Table Of ContentCHEMISTRY
Linington
PROBLEMS IN ORGANIC
Williams
MacMillan
STRUCTURE DETERMINATION
PROBLEMS IN ORGANIC
A Practical Approach to NMR Spectroscopy
STRUCTURE DETERMINATION
“This book is a practical introduction to the world of NMR structure elucidation, starting at a level
where organic chemistry students will feel comfortable, and finishing off with challenging de novo
structure elucidation problems at a level where most organic chemists should be able to improve
S A Practical Approach to NMR Spectroscopy
their skillset.”
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—Prof. Dr. R. Müller, Managing Director of the Helmholtz Institute for Pharmaceutical Research R
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Saarland (HIPS), Head of the Department of Microbial Natural Products
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“Drs. Linington, Williams, and MacMillan have combined their considerable talents and resources to CO
produce an extremely well thought-out book. It can be very strongly recommended to students and T
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practitioners of various levels of ability.” U
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—Dr. A. Douglas Kinghorn, Professor, and Jack L. Beal, Chair of the College of Pharmacy, The Ohio R
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State University and Editor of Journal of Natural Products
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At a point where most introductory organic chemistry texts end, this problems-based workbook picks S
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up the thread to lead students through a graduated set of 120 problems. With extensive detailed I
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spectral data, it contains a variety of problems designed by renowned authors to develop proficiency
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in organic structure determination.
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This workbook leads you from basic problems encountered in introductory organic chemistry MR
textbooks to highly complex natural product-based problems. It presents a concept-based learning G
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platform, introducing key concepts sequentially and reinforcing them with problems that exemplify NA
the complexities and underlying principles that govern each concept.
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The book is organized in such a way that allows you to work through the problems in order or in TI
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selections according to your experience and desired area of mastery. It also provides access to
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raw data files online that can be downloaded and used for data manipulation using freeware or
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commercial software.
With its problem-centered approach, integrated use of online and digital resources, and appendices
that include notes and hints, Problems in Organic Structure Determination: A Practical Approach
to NMR Spectroscopy is an outstanding resource for training students and professionals in structure
determination. Roger G. Linington
K25503
Philip G. Williams
ISBN: 978-1-4987-1962-9
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PROBLEMS IN ORGANIC
STRUCTURE DETERMINATION
A Practical Approach to NMR Spectroscopy
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PROBLEMS IN ORGANIC
STRUCTURE DETERMINATION
A Practical Approach to NMR Spectroscopy
Roger G. Linington
UC Santa Cruz, USA
Philip G. Williams
University of Hawaii, USA
John B. MacMillan
U.T. Southwestern, Texas, USA
Boca Raton London New York
CRC Press is an imprint of the
Taylor & Francis Group, an informa business
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CRC Press
Taylor & Francis Group
6000 Broken Sound Parkway NW, Suite 300
Boca Raton, FL 33487-2742
© 2016 by Taylor & Francis Group, LLC
CRC Press is an imprint of Taylor & Francis Group, an Informa business
No claim to original U.S. Government works
Version Date: 20150909
International Standard Book Number-13: 978-1-4987-1963-6 (eBook - PDF)
This book contains information obtained from authentic and highly regarded sources. Reasonable efforts have been made to publish reliable data and
information, but the author and publisher cannot assume responsibility for the validity of all materials or the consequences of their use. The authors and
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DEDICATION
“This book is dedicated to Professors R. J. Andersen, W. Fenical, W. H. Gerwick, T. F. Molinski,
and the late R. E. Moore who taught us this craft.”
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TABLE OF CONTENTS
Acknowledgements........................................................................................................................ ix
Introduction...................................................................................................................................... xi
Section 1: Structure Confirmation for Simple Molecules........................................................... 1
Section 2: Structure Confirmation for Complex Molecules....................................................... 91
Section 3: Determination of Unknown Structures for Simple Molecules............................... 309
Section 4: Determination of Unknown Structures for Complex Molecules............................ 457
Section 5: Determination of Relative Configurations Using NMR Methods.......................... 637
Section 6: Complex Unknown Natural Product Structure Determination............................. 709
Appendix A: NMR Solvent Reference Chemical Shifts............................................................. 731
Appendix B: Problem Notes........................................................................................................... 732
Appendix C: Problem Hints........................................................................................................... 734
Appendix D: Distribution of Experiment Types......................................................................... 741
Appendix E: Distribution of Functional Groups......................................................................... 745
Appendix F: Selected 15N NMR Chemical Shifts......................................................................... 749
About the Authors........................................................................................................................... 751
About the Spectrometer................................................................................................................... 753
About the Cover............................................................................................................................... 755
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ACKNOWLEDGEMENTS
This work would not have been possible without the efforts of many people. This book
contains spectra from 118 small molecules and well over 500 total experiments, all of
which were acquired under the expert technical skill of Wes Y. Yoshida of the University of
Hawaii. We are indebted to Wes for his significant contribution to this project, including his
dedicated efforts to obtain data of the highest quality, and his seemingly limitless patience
with our shifting requests.
We thank our colleagues William Chain, Jef DeBrabander, Thomas Hemscheidt, Scott Lokey,
Joseph Ready and Uttam Tambar for the generous gifts of chemicals that allowed us to
include such a wide diversity of small molecules.
We have benefited greatly from conversations about the design of this project with members
of the natural products community, many of whom reviewed portions of this book and
provided valuable suggestions. In particular we would like to thank Professors Raymond
Andersen (U. British Columbia), Marcy Balunas (U. Connecticut), William Gerwick (Scripps
Institution of Oceanography, U. California San Diego), Harald Gross (U. Tubingen),
Brian Murphy (U. Illinois-Chicago), Philip Proteau (Oregon State U.) and Ryuichi Sakai
(Hokkaido U.) for their valuable feedback. We also thank the many students and postdocs
who provided comments and worked through many of these problems: Jehad Almaliti,
Judith Bauer, Jingqiu Dai, Amanda Fenner, Joshua Gurr, Isaiah Gomez, Henrik Harms, Mian
Huang, Norbert Kirchner, Shangwen Luom, Henrike Miess, Bailey Miller, Nathan Moss,
Michael Mullowney, Ram Neupane, Stephen Parrish, Anam Shaikh, and Chen Zhang,
Nathaniel Oswald, David Brumley, Dominic Colosimo and Peng Fu.
Dr. Karen S. MacMillan deserves a special thanks, as we took advantage of her attention to
detail to carry out proofreading of the text and quality control of the final spectra.
The staff at CRC press has been extremely helpful in bringing the final product to
completion. In particular we owe a great deal to Hilary LaFoe who has been very supportive
of this project since its inception.
Finally, we hope that you find the problems as challenging, intellectually stimulating, and
enjoyable as we do, and that this text will sharpen your skills in the area of organic structure
determination.
Roger Linington
Philip Williams
John MacMillan
November 2015
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