Abstract
This chapter discusses the chemical properties of 15 of the most important constituents of tobacco. The structural relationships between these alkaloids, their stereochemistry, and the occurrence of enantiomeric forms in nature are also addressed. Information on the physicochemical properties of the alkaloids, i.e., basicity (pKa), and log P values is provided, and the significance of these properties regarding biological activity is discussed. The chapter also deals with electronic structure, oxidation and reduction, N-alkylation and dealkylation reactions, N-acylation reactions, reactions, pyridine ring substitution reactions, pyrrolidine ring substitution reactions, ring opening reactions, resolution and racemization procedures, and other miscellaneous reactions. Finally, it deals with the total synthesis of nicotine and related alkaloids via enantioselective pathways, and the preparation of their isotopic forms.
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