Synthesis, Fourier transform infrared and Raman spectra, assignments and analysis of N-(phenyl)- and N-(chloro substituted phenyl)-2,2-dichloroacetamides

Synthesis, FT-IR, FT-Raman and quantum chemical investigations of N-(3-methylphenyl)-2,2-dichloroacetamide

“…The vibrational spectroscopic analysis of N-(3-methylphenyl)-2,2-dichloroacetamide has not been studied. Thus, in continuation of earlier studies on N-(chloro substituted phenyl)-2,2-dichloroacetamides [1] and N-(2-methylphenyl)-, and N-(4-methylphenyl)-2,2-dichloroacet amides [29], the N-(3-methylphenyl)-2,2-dichloroacetamide (3MPA) of the configuration XyC6H5-y-NHCO-CHCl2 (where, X = CH3 and y = 1) has been synthesised. Spectroscopic and quantum chemical studies were carried out on 3MPA in an effort to provide possible explanations for vibrational frequencies and to understand the effect of methyl group on the characteristic frequencies of amide group.…”

“…As a result of conjugation between the carbonyl bond and the nitrogen lone pair, the C-N bond in amides possesses considerable double bond character thus; one can expect restricted rotation about this bond and a planar configuration for the amide group. This planar structure has been confirmed by measurement with X-rays and the trans-configuration is the most stable and it has been shown that protein chains involve this structure [1][2][3][4][5][6][7][8][9]. N-phenylacetamide is an interesting system because the nearly planar amide group display bond distances, which are close to those found in polypeptides.…”

“…The compound N-(3-methylphenyl)-2,2-dichloroacetamide was synthesized from methylaniline, dichloroacetic acid and phosphorus oxychloride based on the procedure reported [1,29]. The pure samples of 3-methylaniline, dichloroacetic acid and phosphorus oxychloride were purchased from Aldrich chemicals, USA and are used as such without further purification.…”

Comparative vibrational spectroscopic studies of 7-chloro-4- hydroxy-3-quinolinecarboxylic acid based on density functional theory

“…The C-H out-of-plane bending modes are observed in the region 950-600 cm −1 . The aromatic C-H out-of-plane bending vibrations of 7C4H3QCA are assigned to the bands observed at 976, 956, 880 and 831 cm −1 and these bands occurred in the said region [46][47][48]. The density functional theory analysis reveals that the aromatic C-H in-plane and out-of-plane bending vibrations have substantial overlapping with the ring C-C-C in-plane and out-of-plane bending modes, respectively.…”

“…The corresponding C-C and C-N stretching modes observed in the IR spectrum are given in Tables 2. The bands occurring [43][44][45][46]. The density functional theory analysis shows that significant mixing of skeletal in-plane bending with C-H in-plane bending and vice versa occurs.…”