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Pyramidalization of a carbonyl C atom in (2S)-N-(seleno-acet-yl)proline methyl ester.

ABSTRACT: The title compound, C8H13NO2Se, crystallizes as a non-merohedral twin with an approximate 9:1 component ratio with two symmetry-independent mol-ecules in the asymmetric unit. Our density-functional theory (DFT) computations indicate that the carb-oxy C atom is expected to be slightly pyramidal due to an n? ?* inter-action, wherein the lone pair (n) of the Se atom overlap with the anti-bonding orbital (?*) of the carbonyl group. Such pyramidalization is observed in one mol-ecule of the title compound but not the other.

SUBMITTER: Guzei IA 

PROVIDER: S-EPMC3648325 | biostudies-literature | 2013 May

REPOSITORIES: biostudies-literature

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Pyramidalization of a carbonyl C atom in (2S)-N-(seleno-acet-yl)proline methyl ester.

Guzei Ilia A IA   Choudhary Amit A   Raines Ronald T RT  

Acta crystallographica. Section E, Structure reports online 20130430 Pt 5

The title compound, C8H13NO2Se, crystallizes as a non-merohedral twin with an approximate 9:1 component ratio with two symmetry-independent mol-ecules in the asymmetric unit. Our density-functional theory (DFT) computations indicate that the carb-oxy C atom is expected to be slightly pyramidal due to an n→ π* inter-action, wherein the lone pair (n) of the Se atom overlap with the anti-bonding orbital (π*) of the carbonyl group. Such pyramidalization is observed in one mol-ecule of the title comp  ...[more]

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