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Type: Artigo de periódico
Title: Conformational Preferences For N,n-dimethyl-2-haloacetamides (halo=f, Cl, Br And I) Through Theoretical And Experimental Studies: An Unexpected Orbital Interaction
Author: Martins C.R.
Rittner R.
Tormena C.F.
Abstract: Conformational preferences and orbital interactions of N,N-dimethyl-2- fluoroacetamide (1), N,N-dimethyl-2-chloroacetamide (2), N,N-dimethyl-2- bromoacetamide (3) and N,N-dimethyl-2-iodoacetamide (4) were analyzed using experimental infra-red data, theoretical calculations and NBO analysis. The conformational equilibria of compounds 1-4 can be represented by their cis and gauche rotamers. The gauche form of 1 is stable in the vapor phase and in a non-polar solvent, but the cis is predominant in a polar solvent. For 2-4 the gauche form is more stable than the cis, in both the vapor and liquid phases. These conformational preferences were attributed to the orbital interaction between two antibonding orbitals, π* C=O→σ*C-X. This unexpected interaction was possibly due to the high (0.3) electron density on π* C=O, which results from the interaction between one nitrogen lone pair and π*C=O. © 2005 Elsevier B.V. All rights reserved.
Rights: fechado
Identifier DOI: 10.1016/j.theochem.2005.04.033
Date Issue: 2005
Appears in Collections:Unicamp - Artigos e Outros Documentos

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