3789-74-0Relevant articles and documents
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Hodson et al.
, p. 1816,1822 (1958)
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Kinetic Studies of the Deprotonation of Bis(phenylazo)resorcinol Monoanions by Hydroxide Ion
Hibbert, Frank,Simpson, Gareth R.
, p. 1247 - 1254 (2007/10/02)
Interconversion of the intramolecularly Hydrogen-bonded monoanions of 2,4-bis(phenylazo)resorcinol, 4,6-bis(phenylazo)resorcinol, and 2-methyl-4,6-bis (phenylazo)resorcinol with the corresponding dianions in the presence of hydroxide ion in aqueous solution or in 20 percent dioxane-water (v/v) gives complex kinetic behaviour in which the reciprocal relaxation time for the process goes through a minimum value as the hydroxide ion concentration is increased.The results are used to provide a choice between two proposed mechanisms for the similar behaviour of monophenylazoresorcinols.It is argued that the behaviour of monophenylazoresorcinols and bis(phenylazo)resorcinols is compatible with a mechanism for the interconversion of the monoanions and dianions by two simultaneous pathways.One path involves direct attack by hydroxide ion on the hydrogen-bonded proton and in the other path the hydrogen-bonded monoanion is converted into a non-hydrogen-bonded open form from which the proton is removed by hydroxide ion.Values of the rate coefficients for some of these steps are deduced from the kinetic results.