Synthsis of ۲-Arylamido۴-metylthiazol-۵ylacetate andcomparison of its experimental andtheoretical NMR spectra

In this study, to preparation of ۲-Arylamido۴-metylthiazol-۵ylacetate, phenyl isothiocyanate wasadded toAlanine amino acid in the presence of of Acetitril solvent. The reaction was carried out at temperature۴۰-۵۰℃ for ۱۲ hours with good yield [۱]. Thin layer chromatography was used to product confirmation. Thestructure was verified via Nuclear Magnetic Resonance (NMR). Theoretical studies were done on synthesizedcompound. The geometry of the conformers has been optimized (Fig. ۱). Calculations were done by DensityFunctional Theory with B۳LYP method and ۶-۳۱G (d, p) basis set in the vacuum and in the chloroform. ۱Hchemical isotropic shielding of compounds was calculated by Gauge Including Atomic Orbitals method atB۳LYP/۶-۳۱G (d, p) levels of theory. Calculated theoretical ۱H chemical shift values in terms of ppm for C۶-H۱۰-H۱۱-H۱۲, C۱۹-H۲۵-H۲۶-H۲۷, NH-H۹, C۱۷-H۲۲, C۱۸-H۲۴,C۲۱-H۲۹,C۲۳-H۳۰ were ۱.۹۶, ۲.۱۸, ۶.۶۱, ۷.۸۰, ۷.۸۰,۸.۳۵respectively, and also the experimental values in terms of ppm for C۶-H۱۰-H۱۱-H۱۲, C۱۹-H۲۵-H۲۶-H۲۷, NH-H۹,C۱۷-H۲۲, C۱۸-H۲۴,C۲۱-H۲۹,C۲۳-H۳۰were ۲.۱۵, ۲.۳۷, ۷.۲۶, ۸.۳۰, ۸.۳۰,۸.۳۸,۸.۳۸ respectively. The obtainedresults showed that the experimental NMR results are is good agreement with the theoretical ۱H chemical shifts.

کلیدواژه ها:

۲-Arylamido۴-metylthiazol-۵ylacetate ، ، Density Functional Theory