Analysis of the effects of trifluoromethyl group on the conformational properties of meta substituted thioacetanilide

LEZAMA, JOSÉ OSVALDO GUY; ROBLES, NORMA LIS

JOURNAL OF MOLECULAR STRUCTURE

ELSEVIER SCIENCE BV

Año: 2021

0022-2860

Derivatives of thioacetanilide show a conformational equilibrium of the anti and syn forms, anti or syn with respect to the N-H and C=S bonds, respectively, which vary with the different experimental conditions of the sample. The presence of a functional group as a substituent of the aromatic ring adds other conformational possibilities, evidenced in the present study of m-trifluoromethylthioacetanilide through different experimental methodologies. The compound under study was obtained in good yield upon acetylation of the corresponding aniline followed by a thionation according to Curphey's method. The liquid sample was characterized through FTIR, FT Raman and NMR (1H, 13C and 19F) spectroscopies and GC/MS spectrometry. The experimental spectra obtained were analyzed considering data reported for related compounds and quantum chemical calculations derived from Density Functional Theory.