THE SUBSTITUTION EFFECT ON THE AROMATICITY OF SOME N-PHENYLACETAMIDE DERIVATIVES: A DFT STUDY

Autor:	Reza Soleymani, Mahdi Kamaee, Ehsan Fereyduni, Roya Ahmadi
Rok vydání:	2012
Předmět:	Chemistry Electron delocalization Aromaticity Electron Computer Science Applications Crystallography Computational Theory and Mathematics Computational chemistry Polar effect Order (group theory) Substitution effect Density functional theory Physical and Theoretical Chemistry Harmonic oscillator
Zdroj:	Journal of Theoretical and Computational Chemistry. 11:1331-1339
ISSN:	1793-6888 0219-6336
DOI:	10.1142/s0219633612500903
Popis:	The relative aromaticity of some N-phenylacetamide (NPA) derivatives were investigated in which the NPA was substituted by NO2, CN, CF3, Br, Cl, F, H, CH3 , and NH2 groups at two meta and para positions. For this purpose, density functional theory calculations were applied at the B3LYP/6-31+G(d,p) level to calculate the aromaticity indices including nucleus independent chemical shift (NICS), harmonic oscillator model of aromaticity (HOMA) and harmonic oscillator model of electron delocalization (HOMED). The obtained results indicated that the aromaticity of derivatives decreased in the order of NO 2 > CN > CF 3 > Br > Cl > F > H > CH 3 > NH 2 for both meta and para positions. Furthermore, the resulting order was directly related to the electron withdrawing and electron releasing strengths of the substituents. Finally, it was found that all the aromaticity indices of have a good correlation with the Hammett constant.
Databáze:	OpenAIRE
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