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Kinetics and mechanism of the acid‐catalyzed hydration of dihydro‐1,4‐dioxin
Author(s) -
Kresge A. J.,
Yin Y.
Publication year - 1989
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.610020106
Subject(s) - chemistry , catalysis , reactivity (psychology) , kinetic isotope effect , hemiacetal , aqueous solution , kinetics , solvent , substrate (aquarium) , proton , reaction mechanism , ether , medicinal chemistry , vinyl ether , organic chemistry , deuterium , medicine , physics , alternative medicine , oceanography , polymer , pathology , quantum mechanics , copolymer , geology
The cyclic vinyl ether dihydro‐1,4‐dioxin is converted to its cyclic hemiacetal hydration product, 2‐hydroxy‐1,4‐dioxane, in aqueous solution by an acid‐catalyzed reaction for which k H += 1·80 × 10 −5 M −1 S −1 at 25°C. This reactivity and the solvent isotope effect k H +/ k D += 2·2 show that the reaction occurs by rate‐determining proton transfer from catalyst to substrate and not by a pre‐equilibrium mechanism as recently proposed. 2
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