Abstract
Kinetics of interaction of dl-serine, l-proline, l-threonine, and dl-methionine with 3-nitrobenzenesulfonyl chloride in water (40%)—1,4-dioxane and water (40%)—isopropanol mixed solvents was studied spectrophotometrically at 298 K. The main reactive form of α-amino acids is shown to be anionic. Under conditions of arenesulfonylation, the basicity of α-amino acids is crucial in determining the reaction rate. Arenesulfonylation rate constants are 20—50 times lower than the constants of N-acylation of the same α-amino acids with benzoyl chloride and 104–105 times higher than the rate constants of their reactions with benzoic acid 4-nitrophenyl ester.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 900–904, May, 2010.
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Kalinina, N.V., Kustova, T.P. & Kochetova, L.B. Arenesulfonylation of dl-serine, l-proline, l-threonine, and dl-methionine in systems 1,4-dioxane—water and propan-2-ol—water. Russ Chem Bull 59, 922–926 (2010). https://doi.org/10.1007/s11172-010-0186-0
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DOI: https://doi.org/10.1007/s11172-010-0186-0