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

Year 2017, Volume: 4 Issue: 3, 841 - 854, 15.08.2017

Yahya Nural

https://doi.org/10.18596/jotcsa.332034

Cited By: 7

Abstract

Novel 5,5-diphenylpyrrolidineN-aroylthioureas,
containing 4-methylbenzoyl, 2-chlorobenzoyl,2,4-dichlorobenzoyl,
and2-naphthoyl, were synthesized and their structural analysis was performed
using ¹H nuclear magnetic resonance (NMR), ¹³C
NMR, Fourier transform infrared spectroscopy, mass spectrometry (MS), and high-resolution
MS (HRMS) techniques. The acid dissociation constants of the
5,5-diphenylpyrrolidineN-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.

Keywords

Acid dissociation constant, Aroylthiourea, 5-Diphenylpyrrolidine, Potentiometric titration

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