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Equilibrium and kinetic studies of reactions of 2-methyl-2-propanesulfenic acid

✍ Scribed by Tadashi Okuyama; Katsuji Miyake; Takayuki Fueno; Toshiaki Yoshimura; Shinichi Soga; Eiichi Tsukurimichi

Publisher
John Wiley and Sons
Year
1992
Tongue
English
Weight
483 KB
Volume
3
Category
Article
ISSN
1042-7163

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✦ Synopsis

2-Methyl-2-propanesulfenic acid readily undergoes selfcondensation to give S-t-butyl 2-methyl-2-propanethiosufinate. Rates of the reaction were measured in aqueous acetonitrile solution by use o f NMR and UV spectroscopy. The reaction is second order in the substrate. The half-life in a neutral aqueous solution is about 150 hours at 35°C when the initial substrate concentration is 0.003 M . The rate is proportional to acid concentration in the range 0.004-0.2 M . In alkaline solution, the main reaction is selficondensation but some side reactions also seem to occur. The disappearance of the substrate does not follow satisfactory second-order kinetics, but the second-order rate constants obtained by the time-lag method show a maximum around pH 10-11. The pK, (10.47) of the sulfenic acid was obtained at 24°C from a sigmoid curve of the initial absorbances (240 nm) determined by extrapolation of the time-dependent curve.

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