Intramolecular proton-transfer catalysis of nucleophilic catalysis of acetal hydrolysis. The hydrolysis of 8-dimethylamino-1-methoxymethoxynaphthalene
- 1 January 1989
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 7,p. 907-912
- https://doi.org/10.1039/p29890000907
Abstract
The cleavage of the conjugate acid of the title aryl methyl acetal is catalysed efficiently by the neighbouring Me2NH+ group, and also by added nucleophiles. Hydrolysis and nucleophilic catalysis involve a common mechanism, with obligatory but weak bonding to water or the added nucleophile in the transition state. The key to efficient intramolecular proton-transfer catalysis appears to be an intramolecular hydrogen bond between the general acid and the leaving-group oxygen which is strong in the product and transition states, but weak or absent in the ground state.Keywords
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