Year 2017, Volume 4 , Issue 3, Pages 841 - 854 2017-08-15

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

Yahya NURAL [1]


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.

Acid dissociation constant, Aroylthiourea, 5-Diphenylpyrrolidine, Potentiometric titration
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Primary Language en
Subjects Engineering, Engineering, Chemical
Published Date Summer
Journal Section Articles
Authors

Orcid: orcid.org/0000-0002-6204-1241
Author: Yahya NURAL
Institution: Mersin University, Faculty of Pharmacy, Department of Analytical Chemistry
Country: Turkey


Dates

Application Date : July 31, 2017
Acceptance Date : August 10, 2017
Publication Date : August 15, 2017

Vancouver Nural Y . Synthesis and Determination of Acid Dissociation Constants in Dimethyl Sulfoxide–Water Hydroorganic Solvent of 5,5-Diphenylpyrrolidine N-Aroylthiourea Derivatives. Journal of the Turkish Chemical Society Section A: Chemistry. 2017; 841-854.