A. Awwal, F. Hibbert
1977
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Abstract
The conjugate acids of 1,8-bis(dimethylamino) naphthalene and 1,8-bis(diethylamino) naphthalene are intramolecularly hydrogen-bonded, and proton transfers to hydroxide ion in 30%(v/v) dimethyl sulphoxide–water occur slowly, with rate coefficients (kOH–) 6.1 ± 105 and 1.6 ± 104 I mol–1 s–1, respectively. Substitution of ethyl groups for methyl groups in 1,8-bis(dimethylamino)naphthalene has a larger effect on the rate of proton transfer than on the equilibrium constant, and this unusual observation is considered in terms of a two-step mechanism for proton removal from the protonated amines.