Chapter 5 — Further Reading

Textbook treatments of conformational analysis

• Eliel, E. L., and Wilen, S. H. (1994). Stereochemistry of Organic Compounds. Wiley. The 1,200-page reference. Chapters 10-11 cover conformational analysis of acyclic and cyclic molecules in depth.
• Carey, F. A., and Sundberg, R. J. (2007). Advanced Organic Chemistry, Part A, 5th edition. Springer. Chapter 2 on steric and electronic effects.
• Clayden, Greeves, Warren. (2012). Organic Chemistry, 2nd edition. Chapters 16 and 17 on conformation and on equilibrium analysis.

On thermodynamics and kinetics

• Atkins, P., and de Paula, J. (2014). Physical Chemistry, 10th edition. Oxford. The standard undergraduate physical chemistry textbook; chapters 2-9 cover thermodynamics and chapters 21-22 cover kinetics.
• Maskill, H. (1985). The Physical Basis of Organic Chemistry. Oxford University Press. A deeper treatment of energetics specifically for organic chemists.
• Laidler, K. J. (1987). Chemical Kinetics, 3rd edition. Harper & Row. A classic of kinetics pedagogy.

On the Hammond postulate and transition-state theory

• Hammond, G. S. (1955). A correlation of reaction rates. Journal of the American Chemical Society, 77(2), 334–338. The original Hammond paper.
• Marcus, R. A. (1965). On the theory of electron-transfer reactions. Journal of Chemical Physics, 43, 679–701. Marcus theory, which provides the quantitative framework that the Hammond postulate qualitatively captures.
• Bell, R. P. (1980). The Tunnel Effect in Chemistry. Chapman and Hall. For students who want to go beyond classical transition-state theory to understand when quantum tunneling matters.

On the Haber-Bosch process and nitrogen fixation

• Smil, V. (2004). Enriching the Earth: Fritz Haber, Carl Bosch, and the Transformation of World Food Production. MIT Press.
• Hoffman, B. M., Dean, D. R., and Seefeldt, L. C. (2009). Climbing nitrogenase: Toward a mechanism of enzymatic nitrogen fixation. Accounts of Chemical Research, 42(5), 609–619.
• Chirik, P. J. (2009). Nitrogen fixation: One electron at a time. Nature Chemistry, 1, 520–522. On the quest for a molecular catalyst.

On sugar chemistry

• Robyt, J. F. (1998). Essentials of Carbohydrate Chemistry. Springer. A good introduction to the structural chemistry of sugars.
• Stoddart, J. F. (1971). Stereochemistry of Carbohydrates. Wiley. Classic text on sugar stereochemistry, still widely cited.
• Lemieux, R. U. (1975). Cotton Club Chemistry. Royal Society of Chemistry. Lemieux's own account of the elucidation of the anomeric effect — a subtle chair-conformational preference specific to sugars.

Computational tools

• Avogadro: continue to use for all conformational analysis in this book.
• Molecular Operating Environment (MOE): commercial software for advanced conformational searching.
• RDKit: the Python library our pipeline uses; includes conformational search algorithms.