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4-substituted 2-nitrophenylguanidines .2. Acid-base properties and structure

P. Pazdera, M. Potáček, and J. Šimeček

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


Abstract: Dissociation constants KI of the dissociation of 4-X-2-nitrophenyl- guanidinium cation in water (X = H, CH3 , OCH3 , Br, CI, OPh, CN, N02) were measured by potentiometry. A linear dependence of pKI{ on the Hammett constants σp of the substituents X with the value  ϱ=-0.522 was found. Dissociation constants K'II which characterize the dissociation of 4-X-2- -nitrophenylguanidine were measured by the UV VIS spectrophotometric method. A linear dependence was found of pK'II  on Hammett constants  σp- of the substituent X with the value  ϱ=1.143 and a linear correlation between  pK'II and the value of the chemical shift δ of the hydrogen atom H-4.

Full paper in Portable Document Format: 424a539.pdf


Chemical Papers 42 (4) 539–546 (1988)

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