Chemical Education Today
Book & Media Reviews
Organotransition Metal Chemistry by Anthony F. Hill The Royal Society of Chemistry: Cambridge, UK, 2002. 185 pp, ISBN 0471281638 (paperback). $36.95 reviewed by Daniel Rabinovich
The discovery of ferrocene in 1951 marked a turning point in the history of organometallic chemistry, which is today a burgeoning field of fundamental and applied research. At that time very few, if any, thought that the chemistry of compounds containing metal–carbon bonds would some day stand behind myriad industrial processes responsible for the production of chemicals from plastics to pharmaceuticals. This book, a new addition to the ambitious Basic Concepts in Chemistry series being published by the Royal Society of Chemistry, intends to introduce the basic concepts of organotransition metal chemistry to those not familiar with its principles and scope. As such, it underscores the multidisciplinary nature of organometallic chemistry, its value to society, and its beauty as an intellectual pursuit. The book consists of seven chapters, each of which starts with a short list of learning goals or key topics to be covered. Chapter 1 provides the essential concepts necessary for understanding subsequent chapters, from the definition of organometallic chemistry and electron counting rules to ligand types and bonding principles (for example, back-bonding in metal carbonyls, metal–carbon multiple bonds). An overview of bond dissociation energies is then followed by an introduction to the literature of organometallic chemistry, including some sources for further reading, a useful feature that has, regrettably, been omitted from all the other chapters. The first half of Chapter 2 outlines some of the common ligands that often play a supporting (albeit crucial) role in organometallic complexes such as phosphines, aryloxides, arenes, cyclopentadienyls, and poly(pyrazolyl)borates. The second half of this chapter deals with hydride and dihydrogen complexes and their characterization, synthesis, and reactivity. Chapter 3 deals with the syntheses and structures of carbonyl complexes and also includes a succinct section on reactivity (electrophilic, nucleophilic, and migratory insertion reactions). The chemistry of alkyl, aryl, and other σ-bond donor complexes is nicely covered in Chapter 4, and so is that of transition metal carbenes (alkylidenes) and carbynes (alkylidynes) in Chapter 5. Alkenes, alkynes, and related π-bond ligands and an introduction to olefin polymerization reactions are treated in Chapter 6, which even displays in a figure the structures of some modern non-metallocene catalysts (unfortunately, no further information is given about them in the text). Chapter 7 describes allyl complexes and various cyclic polyene ligands, the most important of which are the ubiquitous cyclopentadienyls. There are whole books dedi-
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cated to metallocene chemistry so here the author has been forced to concentrate in a handful of topics, which naturally leads to an uneven coverage of the material. For example, fairly detailed schemes are presented for the reactivity of ferrocene or its dilithiated derivative but virtually nothing is said about the very useful alkyl-substituted cyclopentadienyls (e.g., C5Me5, usually abbreviated Cp*), their properties, and unique applications. The book concludes with an abridged index that needs some serious revamping since key terms highlighted in the text (for example, hydroformylation, homoleptic, NMR, lability, fluxionality, ligand, microscopic reversibility, piano-stool, back-bonding) have not been included. Despite a commendable overall organization of the text and an adequate use of figures, a number of minor typographical errors have escaped the text’s proofreaders (“Tollman” instead of “Tolman” [p 23], “icosohedral” in place of “icosahedral” [p 30], “ispo” in lieu of “ipso” [p 71]). More troublesome is the presence of a few factual mistakes, and as examples I will point out that substituents in the 3-position (not in the 5-position) are the ones closer to the metal in tris(pyrazolyl)borate complexes (p 29), that figure 2.15 (p 32) compares 2J(PH) (cis) versus 2J(PH) (trans) not 1J(PH) versus 2J(PH), and that σ-aryls are only 1- (not 3-) electron donor ligands (p 69). In summary, this book presents a straightforward and quite readable survey of the organometallic chemistry of the transition metals, and I venture to say that it is one of the best in the Basic Concepts in Chemistry collection. However, and I concur with the reviews published in this Journal for other titles in the series, it often overestimates the background knowledge most readers who face organometallic chemistry for the first time may have. So, who should buy or read this book? As a textbook for a strictly undergraduate course in organometallic chemistry, it may well be the best option in the market, and it definitely compares favorably with the two Organometallics primers published by Oxford University Press in 1994 (1). Since I suspect that actually few institutions offer such a class at the undergraduate level (and, if so, probably only as an elective), instructors integrating organometallic chemistry into an inorganic chemistry class may consider it as supplemental reading. Alternatively, the 100-plus pages on organometallic chemistry in widely used inorganic chemistry textbooks such as those by Huheey, Keiter and Keiter (2), Shriver and Atkins (3), or Miessler and Tarr (4) may better serve readers entering the field. Similarly, students and instructors at the graduate level may do better sticking to more mature textbooks such as Crabtree’s The Organometallic Chemistry of the Transition Metals (5), which is the one I’ve been using for a number of years, usually supplemented with information from Elschenbroich and Salzer’s Organometallics (6). (Look out for the new 3rd edition coming out pretty soon!) Last but not least, the book is fairly reasonably priced so anyone having a general interest in organometallic chemistry and a limited budget (don’t we all?) should get a copy as a nice addition to a personal chemistry library.
JChemEd.chem.wisc.edu • Vol. 80 No. 9 September 2003 • Journal of Chemical Education
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Chemical Education Today
Book & Media Reviews Literature Cited 1. (a) Bochmann, M. Organometallics 1; Oxford University Press: New York, 1994. (b) Bochmann, M. Organometallics 2; Oxford University Press: New York, 1994. 2. Huheey, J. E.; Keiter, E. A.; Keiter, R. L. Inorganic Chemistry: Principles of Structure and Reactivity, 4th ed.; HarperCollins: New York, 1993. 3. Shriver, D. F.; Atkins, P. W. Inorganic Chemistry, 3rd ed.; W. H. Freeman: New York, 1999.
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4. Miessler, G. L.; Tarr, D. A. Inorganic Chemistry, 2nd ed.; Prentice-Hall: Upper Saddle River, NJ, 1999. 5. Crabtree, R. H. The Organometallic Chemistry of the Transition Metals, 3rd ed.; Wiley-Interscience: New York, 2001. 6. Elschenbroich, C.; Salzer, A. Organometallics; VCH: New York, 1992.
Daniel Rabinovich is in the Department of Chemistry, The University of North Carolina at Charlotte, Charlotte, NC 28223;
[email protected].
Journal of Chemical Education • Vol. 80 No. 9 September 2003 • JChemEd.chem.wisc.edu
