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libcats.org
Orbital Interaction Theory of Organic Chemistry, 2nd EditionArvi RaukThis is a superb book. There are many books on molecular orbitals. This book, in my opinion, gives the reader a much deeper feel for how MO's actually do Chemistry. I distinguish this from other books because it addresses "why" and "how" questions, whereas most other books seem to stop at "what."
Another thing I found particularly valuable is that the book measures its orbital diagrams using a general C=C ethane energy scale. This helped me appreciate the subtle effects of substituents. The book is somewhat short, and I would characterize the discussion as being deep but not broad. You won't find 10 variations on a mechanism, as in most organic books. What you will find is one or two representative examples of several of the most important mechanisms, but those examples are described much more completely than in other books. I found myself learning more from a few sentences in this book than from pages in other books. The presentation is truly distinct, and incredibly informative. I learned more from this book about how MO's influence Chemistry than almost any other book I have read. Highly recommended!
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