Micellar effects upon the hydrogen ion and general acid catalyzed hydration of 1,4-Dihydropyridines
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Santa Barbara: University of California, 1978. 87 p.
Abstract
The rate limiting step in the hydration of 1-benzyl-l,
4 — dihydronicotinamide (1a) and 1-benzyl-3-acetyl-l, 4-
dihydropyridine (.lb) is; a slow proton transfer, as
shown by the kinetic deuterium solvent isotope effects
and buffer catalysis. Reactions in dilute HC1 are
strongly inhibited by cationic micelles of cetyltrimethylammonium
bromide, CTABr, and the inhibition can
be related to the micellar binding of the substrates
determined spectrophotometrically or by solubility.
Anionic micelles of sodium lauryl sulfate, NaLS, only
weakly catalyze hydration in dilute HC1, and rate constants
go through maxima with increasing [NaLS].