Modern Physical Organic Chemistry

Eric V. Anslyn
The University of Texas, Austin

Dennis A. Dougherty
California Institute of Technology


A Note to the Instructor

Our intent has been to produce a textbook that could be covered in a one-year course in physical organic chemistry. The order of chapters reflects what we feel is a sensible order of material for a one-year course, although other sequences would also be quite viable. In addition, we recognize that at many institutions only one semester, or one to two quarters, is devoted to this topic. In these cases, the instructor will need to pick and choose among the chapters and even sections within chapters. There are many possible variations, and each instructor will likely have a different preferred sequence, but we make a few suggestions here.

In our experience, covering Chapters 1–2, 5–8, selected portions of 9–11, and then 14–16, creates a course that is doable in one extremely fast-moving semester. Alternatively, if organic reaction mechanisms are covered in another class, dropping Chapters 10 and 11 from this order makes a very manageable one-semester course. Either alternative gives a fairly classical approach to the field, but instills the excitement of modern research areas through our use of “highlights” (see below). We have designed Chapters 9, 10, 11, 12, and 15 for an exhaustive, one-semester course on thermal chemical reaction mechanisms. In any sequence, mixing in Chapters 3, 4, 12, 13, and 17 whenever possible, based upon the interest and expertise of the instructor, should enhance the course considerably. A course that emphasizes structure and theory more than reactivity could involve Chapters 1–6, 13, 14, and 17 (presumably not in that order). Finally, several opportunities for special topics courses or parts of courses are available: computational chemistry, Chapters 2 and 14; supramolecular chemistry, Chapters 3, 4, and parts of 6; materials chemistry, Chapters 13, 17, and perhaps parts of 4; theoretical organic chemistry, Chapters 1, 14–17; and so on.

One of the ways we bring modern topics to the forefront in this book is through providing two kinds of “highlights”: Going Deeper and Connections. These are integral parts of the textbook that the students should not skip when reading the chapters (it is probably important to tell the students this). The Going Deeper highlights often expand upon an area, or point out what we feel is a particularly interesting sidelight on the topic at hand. The Connections highlights are used to tie the topic at hand to a modern discipline, or to show how the topic being discussed can be put into practice. We also note that many of the highlights make excellent starting points for a five- to ten-page paper for the student to write.

As noted in the Preface, one goal of this text is to serve as a reference when a student (or professor) is reading the primary literature and comes across unfamiliar terms, such as “dendrimer” or “photoresist.” However, given the breadth of topics addressed, we fully recognize that at some points the book reads like a “topics” book, without a truly in-depth analysis of a given subject. Further, many topics in a more classical physical organic text have been given less coverage herein. Therefore, many instructors may want to consult the primary literature and go into more detail on selected topics of special interest to them. We believe we have given enough references at the end of each chapter to enable the instructor to expand any topic. Given the remarkable literature-searching capabilities now available to most students, we have chosen to emphasize review articles in the references, rather than exhaustively citing the primary literature.

We view this book as a “living” text, since we know that physical organic chemistry will continue to evolve and extend into new disciplines as chemistry tackles new and varied problems. We intend to keep the text current by adding new highlights as appropriate, and perhaps additional chapters as new fields come to benefit from physical organic chemistry. We would appreciate instructors sending us suggestions for future topics to cover, along with particularly informative examples we can use as highlights. We cannot promise that they will all be incorporated, but this literature will help us to keep a broad perspective on where the field is moving.

Given the magnitude and scope of this project, we are sure that some unclear presentations, misrepresentations, and even outright errors have crept in. We welcome corrections and comments on these issues from our colleagues around the world. Many difficult choices had to be made over the six years it took to create this text, and no doubt the selection of topics is biased by our own perceptions and interests. We apologize in advance to any of our colleagues who feel their work is not properly represented, and again welcome suggestions.

            We wish you the best of luck in using this textbook.