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Type: Artigo de periódico
Title: Conformational isomerism and electronic interactions in some alpha-aminoketones
Author: Ducati, LC
Rittner, R
Custodio, R
Abstract: The theoretically calculated potential energy surfaces (PES), at MP2/6-31G (d,p) level of theory, for the alpha-aminoacetone and alpha-aminocyclohexanone showed the occurrence of two conformers for the former, being the synperiplanar (Sp) 3.00 kcal mol(-1) much more stable than the synclinal (Sc) conformer, while three axial [two Sc and one Ap (antiperiplanar)] and one equatorial (Ap) conformers were observed for the later, with the Ap-eq as the most stable conformation (2.07 kcal mol(-1) from the lower energy axial conformer). For the more complex system, the N,N-dimethyl-alpha-aminoacetone, a 3D potential energy surface was obtained, which led to two stable conformers (Sc-Sc and Sp-Ap; Delta Esp-Ap-sc-sc=0.81 kcal mol(-1)) and two transition states (Sc-Sc-T and Ap-Sp(T)), when the equivalent forms bringing an specular relationship are discarded. The stability of the different conformers for the three studied compounds were explained by the orbital interactions obtained through NBO calculations. (c) 2006 Elsevier B.V. All rights reserved.
Subject: alpha-aminoketones
theoretical calculations
orbital interactions
Country: Holanda
Editor: Elsevier Science Bv
Rights: fechado
Identifier DOI: 10.1016/j.theochem.2006.04.021
Date Issue: 2006
Appears in Collections:Artigos e Materiais de Revistas Científicas - Unicamp

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