Synthetic, Infrared And Nmr (¹H And ¹³C) Spectral Studies Of N-(Substituted Phenyl)-Methanesulphonamides

Abstract

Twenty two N-(substituted phenyl)-methanesulphonamides of the general formula, CH 3 SO 2 NHR, where R = 4-XC 6 H 4 (X = H, CH 3 , F, Cl, Br or NO 2 ), i-XC 6 H 4 (X = CH 3 , Cl or NO 2 and i = 2 or 3) and i, j-X 2 C 6 H 3 (i, j-X 2 = 2,3-(CH 3 ) 2 , 2,4-(CH 3 ) 2 , 2,5-(CH 3 ) 2 , 2,6-(CH 3 ) 2 , 3,5-(CH 3 ) 2 , 2,3-Cl 2 , 2,4-Cl 2 , 2,5-Cl 2 , 2,6-Cl 2 or 3,4-Cl 2 ) were prepared, characterized and their infrared spectra in the solid state and the NMR ( 1 H and 13 C) spectra in solution studied. The N-H stretching vibrations absorb in the range, 3298 -3232 cm −1 . Asymmetric and symmetric SO 2 stretching vibrations appear as strong absorptions in the ranges, 1331 -1317 cm −1 and 1157 -1139 cm −1 , respectively. The sulphonamides exhibit S-N stretching vibrations in the range, 926 -833 cm −1 . The effect of substitution in the phenyl ring in terms of electron withdrawing and electron donating groups is non-systematic. The 1 H and 13 C chemical shifts of N-(substituted phenyl)-methanesulphonamides are assigned to various protons and carbons of the compounds. Further, incremental shifts of the ring protons and carbons due to CH 3 SO 2 -and CH 3 SO 2 NH-groups in the N-(phenyl)-methanesulphonamide are computed and used to calculate the 1 H and 13 C chemical shifts of various protons and carbons of N-(substituted phenyl)-methanesulphonamides, by adding substituent contributions to the corresponding aromatic proton or carbon chemical shifts of either aniline, substituted anilines, benzene or substituted benzenes, in different ways, as per the principle of substituent addition. The computed values by different procedures agree well with each other and with the experimental chemical shifts. The correlation of these incremental shifts with the Hammett substituent parameters is poor.

Quantum chemical studies, spectroscopic analysis and molecular structure investigation of 4-Chloro-2-[(furan-2-ylmethyl)amino]-5-sulfamoylbenzoic acid

“…The bands observed at 1310 and 1251 cm -1 in the FT-Raman spectrum, and 1316 cm -1 in the FT-IR spectrum, were assigned to antisymmetric S=O stretching vibrations. A coincidence between the experimental values with those of the literature [44][45][46] and the theoretical results are found for the above conclusions. The bending vibrations of O=S=O also given in Table 2.…”

“…The symmetric and asymmetric SO2 stretching vibrations occur in the regions of 1125-1150 cm -1 and 1295-1330 cm -1 [29]. The symmetric S=O stretching vibrations at 1096 and 1095 cm -1 , by the DFT calculations, are seen as pure modes [44], while these bands were obtained at 1153 and 1146 cm -1 in the FT-IR spectrum [45]. Dodoff [46] recorded the symmetric stretching mode at 1150 cm -1 as a strong peak, and the antisymmetric modes at 1341 and 1351 cm -1 in the infrared spectrum for N-3pyridinylmethanesulfonamide.…”

N-(4-Nitrophenyl)methanesulfonamide

“…For related literature, see: Gowda et al (2000); Gowda et al (2007); Gowda et al (2007a), (2007b); Jayalakshmi & Gowda (2004); Klug (1968).…”

“…The title compound was prepared according to the literature method of Jayalakshmi & Gowda (2004). The purity of the compound was checked by determining its melting point.…”

“…The purity of the compound was checked by determining its melting point. It was characterized by recording its IR and NMR spectra (Jayalakshmi & Gowda, 2004). Single crystals of the title compound were obtained by slow evaporation of an ethanolic solution and used for X-ray diffraction studied at room temperature.…”