17102-23-7Relevant articles and documents
Synthesis, FTIR and FT-Raman spectral analysis and structure-activity relations of N-(4-bromophenyl)-2,2-dichloroacetamide by DFT studies
Arjunan,Senthilkumari,Ravindran,Mohan
, p. 15 - 26 (2014)
The FTIR and FT-Raman vibrational spectra of N-(4-bromophenyl)-2,2- dichloroacetamide molecule has been recorded and analysed the complete vibrational fundamental modes of the most stable geometry of the compound using the experimental FTIR and FT-Raman data on the basis of peak positions, relative intensities and quantum chemical studies. The observed vibrational frequencies were compared with the theoretical wavenumbers of the optimised geometry of the compound obtained from the DFT-B3LYP gradient calculations employing the high level 6-311++G** and cc-pVTZ basis sets. The effect of substituent Br in the amide moiety have been analysed and compared. The kinetic and thermodynamic stability and chemical reactivity descriptors of the molecule have been determined. The reactive centres are found from the molecular electrostatic potential and the atomic charges. The limits of electrostatic potential are -9.617e × 10-3 and +9.617e × 10 -3. The molecule has great electronegativity difference, charge is very polarized, and there are significant differences in electron density in different regions of the molecule. The lone pair donor orbital, nN → π*CO interaction possess a strong stabilisation of 64.21 kcal mol-1.
Synthesis and characterization of N-acylaniline derivatives as potential chemical hybridizing agents (CHAs) for wheat (Triticum aestivum L.)
Chakraborty, Kajal,Devakumar
, p. 6800 - 6808 (2007/10/03)
Induction of male sterility by deployment of chemical hybridizing agents (CHAs) are important in heterosis breeding of self-pollinated crops like wheat, wherein the male and female organs are in the same flower. Taking a lead from the earlier work on rice, a total of 25 N-acylanilines comprising of malonanilates, acetoacetanilides, and acetanilides (including halogenated acetanilides) were synthesized and screened as CHAs on three genotypes of wheat, viz., PBW 343, HD 2046, and HD 2733 at 1500 ppm in the winter of 2001-2002. The N-acylanilines containing variations at the acyl and aromatic domain were synthesized by condensation of substituted anilines with appropriate diesters, acid chlorides, or monoesters. The test compounds with highly electronegative groups such as F/Br at the para position of the aryl ring were identified as the most potent CHAs, causing higher induction of male sterility. A variation of N-substitution at the side chain generally furnished analogues like 4′-fluoroacetoacetanilide (7) and ethyl 4′-fluoromalonanilate (1), which induced 89.12 and 84.66% male sterility, respectively, in PBW 343. Among halogenated acetanilides, the increasing number of chlorine atoms in the side chain led to an increase in the activity of 4′-fluoro (23) and 4′-bromo (24) derivatives of trichoroacetanilides, which induced >87% male sterility. Quantitative structure-activity relationship (QSAR) models indicated the positive contributions of the field effect exemplified by the Swain-Lupton constant (Fp) and negative contributions of the Swain-Lupton resonance constant (R) for the aromatic substitution. The positive influences of parachor (P) for the acyl domain have been underlined. These leads will be significant in explaining the CHA fit in the macromolecular receptor site. The CHAs appeared to act by causing an imbalance in the acid-base equilibrium in pollen mother cells resulting in dissolution of the callose wall by premature callase secretion.
Photochemical Bromination of Anilides by Benzenehexabromide
Aly, M. M.,Awad, I. M. A.,Fahmy, A. M.
, p. 77 - 80 (2007/10/02)
Benzenehexabromide was found to afford photochemical bromination of substituted acetanilide in the p-position.The rates of bromination were found to follow the order predicted on the basis of inductive effect of the substituents and similar to the sequence of reactivities observed for bromination of acetanilides with N-bromosuccinimide.Similar results were obtained in the case of p-substituted benzanilides and the reaction shows a good Hammett correlation with the ?+ values for the substituents with a ρ value -0.266.
