Organic detective work

Organic structure analysis

Phillip Crews, Jamie Rodriguez and Marcel Jaspars 

New York, US: Oxford University Press USA 2010 | 656pp | ?85.00 (HB)

ISBN 9780195336046

Reviewed by David O’Hagan

This is the second edition of an excellent book on the structure elucidation of complex natural products. It is written by three experts with international reputations in natural product structure determination.

The book is aimed at undergraduates, graduate students and practitioners as they develop expertise in the structural elucidation of organic compounds. It is particularly appropriate for undergraduate teaching.

Topics covered include nuclear magnetic resonance (NMR), mass spectrometry (MS), infrared (IR), ultraviolet (UV), circular dichroism (CD) and optical and chiroptical (UV, CD and optical rotatory dispersion (ORD)) methods. Five chapters of the book focus on NMR. There are excellent NMR chemical shift tables, and the text develops extremely well from the basics of ¹H- and ¹³C-NMR, through multidimensional techniques nuclear Overhauser effect spectroscopy (NOESY), rotating frame NOESY (ROESY) and total correlation spectroscopy (TOCSY), progressing to decoding stereochemical issues using Murata’s homo- and heteronuclear coupling constant relationships.

Chapters on mass spectrometry outline the principles of MS and explain modern ionisation techniques, giving nice descriptions of, for example, quadrupole and linear ion trap analysers, time of flight detectors, ion cyclotron resonance, ion mobility mass analysers. Tandem MS/MS methods are very well described with excellent illustrations.

One extensive chapter is committed to IR, covering the fundamentals of functional group identification with extended and useful IR frequency tables.

The chapter on optical and chiroptical methods covers UV, CD, ORD and covers a basic introduction to chromophore identification.

The book fits very well the problem-solving workshop approach used to teach organic structure elucidation in undergraduate courses, certainly in UK universities.

At the end of the book there are 51 ’unknowns’ where a compilation of spectra is provided to solve a structure. The problems range from straightforward examples to very challenging ones. Answers are given as three possible chemical abstract service (CAS) numbers, and from there the students have to unambiguously identify a structure. For the casual reader, confirming the structure is probably too much like hard work, but it is an excellent code for workshop teaching. The spectral reproduction of the ’unknowns’ is uniformly excellent and in this respect the book offers an excellent repository of problems for teaching.

Overall this text is more comprehensive and more detailed in introductory descriptions than the classic text in the area - Spectroscopic methods in organic synthesis by Williams and Fleming. It is less of a handbook for PhDs, and post docs and will find its greatest utility as a substantial text for undergraduate teaching. In this respect it is the best around.