Pyramidalization of a carbonyl C atom in (2S)-N-(seleno­acet­yl)proline methyl ester

The title compound, C(8)H(13)NO(2)Se, crystallizes as a non-merohedral twin with an approximate 9:1 component ratio with two symmetry-independent mol­ecules in the asymmetric unit. Our density-functional theory (DFT) computations indicate that the carb­oxy C atom is expected to be slightly pyramidal...

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Detalles Bibliográficos
Autores principales: Guzei, Ilia A., Choudhary, Amit, Raines, Ronald T.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2013
Materias:
Organic Papers
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3648325/
https://www.ncbi.nlm.nih.gov/pubmed/23723945
http://dx.doi.org/10.1107/S1600536813011112
Descripción
Sumario:The title compound, C(8)H(13)NO(2)Se, crystallizes as a non-merohedral twin with an approximate 9:1 component ratio with two symmetry-independent mol­ecules in the asymmetric unit. Our density-functional theory (DFT) computations indicate that the carb­oxy C atom is expected to be slightly pyramidal due to an n→ π* inter­action, wherein the lone pair (n) of the Se atom overlap with the anti­bonding orbital (π*) of the carbonyl group. Such pyramidalization is observed in one mol­ecule of the title compound but not the other.

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