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Synthesis

What's New at the Chemistry Library

by Stephen K. Ritter
June 26, 2006 | A version of this story appeared in Volume 84, Issue 26

There are more chemistry reference books and websites now available than you can shake a stick at. Reference works on organic reaction chemistry tend to be the most common, as organic synthesis is the meat-and-potatoes of chemistry. In the past year, several new books of note among the dozens available in this genre have been published. Nearly all of these types of books are good, or at least useful, at some level. Choosing one to have at your fingertips tends to be subjective.

Reactions named after chemists who devised a particular synthesis or process, such as the Grignard reaction or the Wittig reaction, are central to organic chemistry. One of the most informative books ever produced on this topic may be "Strategic Applications of Named Reactions in Organic Synthesis: Background and Detailed Mechanisms," by László Kürti and Barbara Czakó. Kürti and Czakó are graduate students of Amos B. Smith III and Gary A. Molander, respectively, at the University of Pennsylvania. Their compilation includes a list of common abbreviations followed by information on 250 named reactions. Also included are common reactions that don't have a namesake, such as the Nobel Prize-winning olefin metathesis.

Each reaction is laid out on two facing pages in the book and begins with a description of the reaction and its importance, related reactions, and improvements made to the reaction over time. A color-coded reaction scheme with a description of the mechanism is included, as is a section on synthetic value and examples of applications. The book includes some 10,000 references to key papers and reviews on the reactions. It's available from Elsevier in paperback, hardcover, or CD ($94.95) or hardcover with CD ($169.95).

The text is prefaced by complimentary comments from Nobel Laureate E. J. Corey of Harvard University and from K. C. Nicolaou of Scripps Research Institute. "The essence of the art and science of synthesis comes alive from the pages of this wonderful text," Nicolaou writes. The book should serve "as an inspiration to today's students to discover, invent, and apply their own future named reactions," he adds.

Not to be outdone is Elbertus Kruiswijk's "The Comprehensive E-book of Named Organic Reactions and Their Mechanisms," another pivotal reference for organic chemists. As the title implies, the book is available only in electronic format (e-book, running on Adobe Acrobat), and it is comprehensive, covering more than 1,300 named reactions that occupy nearly 2,800 pages.

Kruiswijk began writing the book about 10 years ago as an undergraduate student at the University of Utrecht, in the Netherlands. He went on to complete his Ph.D. degree in chemistry at the University of Wales. Following postdoctoral work and training as a secondary school teacher, he is now self-employed writing chemistry reference books and educational materials.

Kruiswijk aimed for the e-book to be "comprehensive," because most books of this type usually cover only the 300 or so best-known named organic reactions, he writes. Each reaction entry includes an example reaction scheme, a mechanism or proposed reaction pathway scheme, and a retrosynthesis reaction scheme showing a plausible connection between the product and potential starting compounds. A section of notes provides a description of the chemistry and includes related or alternative reactions, along with cross-references to other reactions in the book. More than 7,200 literature references are included and are current up to January of this year.

Overall, the entries for the reactions in Kruiswijk's book aren't as detailed as those in Kürti and Czakó's book, and some reactions, such as olefin metathesis, aren't included because they are not associated with a chemist's name. But the roughly $27 (£14.95) cost, which includes free upgrades, is very attractive. The e-book can be downloaded from www.namedorganicreactions.co.uk.

Additional organic chemistry references published in the past year include the second edition of "Name Reactions and Reagents in Organic Synthesis," by Bradford P. Mundy, Michael G. Ellerd, and Frank G. Favaloro Jr. This book has more than 500 reactions and updates the original, which was published in 1988. It's available from Wiley in hardcover and as an e-book ($94.50). The second edition of "Named Organic Reactions," by Thomas Laue and Andreas Plagens, also is out. It includes 134 reactions and has detailed descriptions like a textbook. It updates the original, which was published in English in 1998, and is available from Wiley in paperback ($55) or hardcover ($130) and as an e-book ($125).

Another updated reference is the 10th edition of "Reagent Chemicals: Specifications and Procedures," which is produced by the American Chemical Society's Committee on Analytical Reagents. This edition coincides with the 100th anniversary of the ACS guidelines for reagent chemicals. The new specifications, official from Jan. 1 of this year, replace the specifications set in the ninth edition that went into effect in 2000. It's available from Oxford University Press in hardcover and online from ACS at pubs.acs.org/reagents.

Yet another set of handy reference books is the "Instant Notes" chemistry series by Garland Science/BIOS Scientific Publishers. The second editions of the organic chemistry and inorganic chemistry books became available during the past two years, and books on physical, medicinal, and analytical chemistry were published about five years ago. (Biochemistry and molecular biology books are available as part of a different series.) These books are appealing for capturing the basics of chemistry's primary disciplines in a focused and informative format that leaves out many extraneous details common to textbooks. They are each available at the sensible price of $33.95.


Also of interest

Books

THE ORGANIC CHEMISTRY OF BIOLOGICAL PATHWAYS, by John E. McMurray and Tadhg P. Begley, Roberts, 2005, 490 pages, $92 (ISBN 0-97-470071-6)

PROTECTING GROUPS (Third Edition), by Philip J. Kocien´ski, Thieme, 2005, 679 pages, $89.95 (ISBN 1-58890-376-1)

DRUG DISCOVERY HANDBOOK, edited by Shayne Cox Gad, Wiley-Interscience, 2005, 1,471 pages, $160 (ISBN 978-0-471-21384-0)

Websites

TOXICOLOGY DATA NETWORK National Institutes of Health site has databases on toxicology, hazardous chemicals, environmental health, and toxic releases; free at toxnet.nlm.nih.gov

NIST CHEMISTRY WEBBOOK National Institute of Standards & Technology site has comprehensive physical data and health and safety information on chemicals; free at webbook.nist.gov/chemistry

WEBELEMENTS Developed by Mark J. Winter at the University of Sheffield, in England, this was the first electronic periodic table available on the World Wide Web (1993) and has detailed data on all the elements; free at www.webelements.com


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