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Kinetics of cyclization of N-substituted 1-(2-nitrophenyl)-guanidines and mechanism of the cyclization reactions

P. Pazdera and M. Potáček

Department of Organic Chemistry, Faculty of Natural Sciences, J. E. Purkyně University, CS-611 37 Brno

 

Abstract: Kinetic measurements of cyclization of 3-ethyl-l-(2-nitrophenyl)guanidine and 2-phenyl-l-(2-nitrophenyl)guanidine to 3-ethyl- and 3-phenylamino-l,2,4-benzotriazine 1-oxide were carried out in dependence on pH of the reaction medium by spectrophotometry. The rate constants kI calculated for the unimolecular order of the reac­tion were proved to be linearly dependent on pH of the medium. Also the rate constants kIIfor the bimolecular order of the reaction were calculated. From the results of this kinetic study and the published experimental findings about the properties of 2-nitrophenylguanidines and their cycliza­tion to substituted 3-amino-l,2,4-benzotriazine 1-oxides the mechanism of this base-catalyzed reaction was proposed.

Full paper in Portable Document Format: 442a241.pdf

 

Chemical Papers 44 (2) 241–248 (1990)

Wednesday, August 10, 2022

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