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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)

Kinetics of trans-cinnamic anhydride reactions catalyzed by pyridine, 4-dimethylaminopyridine, and N-methylimidazole.

The kinetics of hydrolysis of trans-cinnamic anhydride and of its reactions with hydroxy compounds were studied in the presence of pyridine, 4-dimethylaminopyridine, and N-methylimidazole as catalysts. The absolute rates of the catalyzed hydrolysis decreased with increasing acetonitrile content (decreasing solvent polarity), but the catalytic efficiency of N-methylimidazole and 4-dimethylaminopyridine relative to pyridine increased as the solvent polarity decreased. The relative catalytic rates for the cinnamoylation of n-propanol in acetonitrile were 1:259:16,000 for pyridine, N-methylimidazole, and 4-dimethylaminopyridine, respectively.[1]


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