pK a Determination of Newly Synthesized N‑(benzothiazole-2-yl)-2-(4,5-dimethyl-1-(phenylamino)-1H-imidazol-2-ylthio)acetamide Derivatives

• Published in: Industrial & engineering chemistry research 2013-06, Vol.52 (25), p.8355-8360
• Main Authors: Duran, Murat, Canbaz, Mehmet Çetin
• Format: Article
• Language: English
• ISSN: 0888-5885; 1520-5045
• DOI: 10.1021/ie400316r

In this work, nine drug precursors, 2-(4,5-dimethyl-1-(phenylamino)-1H-imidazol-2-ylthio)-N-(benzothiazole-2-yl) acetamide derivative compounds, were newly synthesized by reacting 4,5-dimethyl-1-(phenylamino)-1H-imidazole-2(3H)-thione derivatives with 2-chloro-N-(thiazol-2-yl) acetamide compounds. Structures of the synthesized compounds were confirmed by 1H NMR, FTIR (Fourier transform infrared), MS (mass spectroscopy), and elemental analysis. The acidity constants of these acetamide derivatives were determined via UV spectroscopic studies. It was found that the first protonation of these compounds occurs on the nitrogen at imidazole ring, while the second protonation of these compounds occurs on the nitrogen at benzothiazole ring. The first pK a values were found to vary between 5.91 and 8.34 while the second pK a values were varying between 3.02 and 4.72.