Synthesis and Determination of Acid Dissociation Constants in Dimethyl Sulfoxide–Water Hydroorganic Solvent of 5,5-Diphenylpyrrolidine N-Aroylthiourea Derivatives

Abstract

Novel 5,5-diphenylpyrrolidine N -aroylthioureas, containing 4-methylbenzoyl, 2-chlorobenzoyl,2,4-dichlorobenzoyl, and2-naphthoyl, were synthesized and their structural analysis was performed using 1 H nuclear magnetic resonance (NMR), 13 C NMR, Fourier transform infrared spectroscopy, mass spectrometry (MS), and high-resolution MS (HRMS) techniques. The acid dissociation constants of the 5,5-diphenylpyrrolidine N -aroylthiourea derivative compounds were determined using Hyperquad computer program for data obtained using potentiometric titration method in 25% (v/v) dimethyl sulfoxide–water hydroorganic solvent in the presence of 0.1 mol × L - 1 ionic strength of NaCl and in the acidic medium at 25±0.1°C, using sodium hydroxide base as a titrant. Two acid dissociation constants were obtained for 3a , 3b, and 3d, and it was suggested that they were related to N-H and enol groups. Furthermore, three acid dissociation constants obtained for 3a indicated that they were related to N-H, enthiol, and enol groups, and four acid dissociation constants obtained for 3c suggested that they were related to N-H, enthiol, enol, and carboxyl groups.