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Revista de la Sociedad Química de México
versão impressa ISSN 0583-7693
Resumo
MADRID, Gustavo; QUIROZ, Beatriz e CUEVAS, Gabriel. Estudio experimental y computacional de la participación de efectos estereoelectrónicos en derivados del norbornano sustituidos en posición 2 por medio de las constantes de acoplamiento 1JC-C. Rev. Soc. Quím. Méx [online]. 2000, vol.44, n.1, pp.53-61. ISSN 0583-7693.
In this paper the analysis of 1JC-C coupling constants shown that they are good indexes for stereoelectronic effects participation in the stability of organic molecules. Within this analysis, experimental and computational data were found and allows to explain the very well known differences of the kinetic behavior in endo- and exo 2-norborneol derivatives. These coupling constants show the stereo electronic delocalization between O-R polar bonds and C-C bonds which present the appropriated stereochemical disposition to have interaction in the ground state. Experimental coupling constants were measured by INADEQUATE technique and were calculated by ab initio calculations using density functional theory (DFT). As it is showed, the endo-derivatives are stabilized by a stereoelectronic σC1-C7 → σ*C2-OR type interaction whereas the corresponding exo isomers are stabilized by a σC1-C6 → σ*C2-OR stereoelectronic interation.
Palavras-chave : Stereoelectronic effects; INADEQUATE; norbornanes; stabilization; coupling constants.