Book Reviews

A Future of the History of Chemical Information

A Future of the History of Chemical Information (ACS Symposium Series) American Chemical Society, McEwen, Leah Rae (Editor), Robert E. Buntrock (Editor)  2014, ISBN 9780841229457

This book is a must read for science librarians, information professionals, and researchers who need a primer on the chemical information landscape. Each chapter in this book covers a different area of chemical information and its evolution including patents, mobile device apps the evolution of chemical databases (CAS, and Reaxys for example), open access databases and resources, chemical ontology, the semantic web, and even spectral data. Some common themes emerge from many of the chapters. For example, although the delivery of chemical information has shifted from print to electronic resources, the need to know where to find such information and how to formulate useful search strategies remains key. Researchers should still spend time keeping current with the literature in their area and beyond. Print may be becoming obsolete but the need to browse the literature is not. As the saying goes (or words to that effect), a few hours in the library can save a few weeks in the laboratory. Although researchers may not walk into a physical library space, they do need to consult the right information-based tools whether they are databases accessed from the lab or applications used while waiting in the airport. 

As a science librarian, I found Judith Currano’s chapter on teaching chemical information especially informative and helpful. I too have spent far too much time showing students how to navigate databases without challenging them how to think about the actual information they are seeking. She discusses some key principles that students need to learn in order to effectively search for chemical information such as understanding the scope and organization of resources and realizing that not all information resources are created equal. Some authors in this book hint that librarians in the field may be outliving their usefulness but after reading Currano’s chapter it is clear that librarians are here to stay.

Another interesting theme that arose is the need for open access articles, data, electronic lab notebooks and other related resources that can promote collaboration and corroboration of the data.  It seems to me that much of this talk of open access and open data is quite idealistic in a field that is seemingly resistant to such concepts (at least in my limited experience). Who will put pressure on Elsevier and ACS?  Who will share data and what data will they share?  I would love to see a future title that seriously examines the obstacles and resistance both from publishers and researchers themselves that open access information and open data face. 

Patti McCall
University of Central Florida
patti.mccall@ucf.edu

Computational Organic Chemistry

Book Reviews
Computational Organic Chemistry, 2nd Edition; Bachrach, Steven M.; John Wiley & Sons, Hoboken, NJ, 2014: pp 1-632 + xiii, ISBN 978-1-118-29192-4 (hardcover), $125.

Even though he reported on the field via a blog in the 7 years since the first edition was published, the author decided to publish a welcome second edition. The key concept to both is the application of Quantum Mechanics (QM) for description of chemical reactions and properties. Use of these principles, aided of course by ever increasing computing power, is being used to determine details in both reactivity and structure determination of chemical compounds.  Much of the material has been updated including two new chapters on spectroscopy and enzymes.

The Preface is probably the best review of both the book and the field of computational organic chemistry, beginning with the history and rapid evolution of the field. For molecules the size and complexity of organic molecules, the fundamental Schrödinger equation (if solvable, the key to all molecular properties) cannot be solved exactly so a number of approximations are necessary to facilitate the process  For simplicity only ab initio methods (from basic principles) are considered which, given the continual increase in computing power, become increasingly practical. The ready availability of the number of computer programs also facilitates growth and practice.

The book is aimed both at existing or potential practitioners of computational chemistry and the latter can include both prospective occasional users or graduate students seeking an entry into the field. According to the author, prior expertise in quantum chemistry is not necessary to read the book but the QM taught in a typical undergraduate physical chemistry course should suffice. Chapter 1 is an introduction to the field, its concepts and definitions of the myriad abbreviations used. It can be used to better the understanding of subsequent chapters. Chapter 2 is on spectroscopy and the ability to use calculated spectra in structure determination. Chapter 3 is a brief introduction to several concepts of organic chemistry—including isomerism, acidity, and aromaticity—amenable to the application of computational studies.  Chapter 4 covers pericyclic reactions including my favorite, the Diels-Alder reaction. Radicals, and carbenes are covered in Chapter 5 and carbanions as well as organic catalysis in Chapter 6. Solvent effects are the subject of Chapter 7 and dynamic effects in reactions in Chapter 8. Although many biochemical molecules are too large for effective computation, the smaller molecules involved are covered in Chapter 9, the other new chapter.

The author emphasizes the personal aspects of the field. The first edition contained, at the end of several chapters, six interviews with a computational chemist working in that particular aspect, including the late Paul Schleyer. These are reprinted in this second edition and three additional interviews have been added. The book is lavishly illustrated, references are at the end of each chapter, and the index is extensive. The author maintains an associated website (www.comporgchem.com) to supply supporting information. In addition, the related blog (www.comporgchem.com/blog) will provide updates to the material in the book and is intended to serve a two-way function with reader comments welcome.

The reviewer’s educational background—50 years ago—and a math background that plateaued with an incomplete perception of matrices provides additional challenges for full comprehension. Nevertheless, I’ve developed an appreciation for what QM and computational chemistry can do for our understanding of chemistry.  I was especially pleased when, in both editions, the author described the controversy generated by Dewar 30 years ago that the mechanism of the Diels-Alder reaction was not concerted (i.e., that the formation of the new bonds was sequential and not simultaneous). However, Dewar was using semiempirical calculations whereas ab initio methods confirm other studies that the reactions are concerted and synchronous.  Other pericyclic reactions are also covered but I’m curious whether any computational work has been done on the related Ene reaction.

Why is this book being reviewed in the CIB?  It is a treatise in the broader field of chemical information, of value to others than practitioners.  Also the number of venues for book reviews in both chemical information and computational chemistry has become increasingly limited.  An additional disclaimer: I’ve known the author for 20 years and have found his contributions to our field of chemical information to be valuable. Recommended for the audiences described in the third paragraph.

Robert E. (Bob) Buntrock
Orono, ME
buntrock16@roadrunner.com