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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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
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author Guzei, Ilia A.
Choudhary, Amit
Raines, Ronald T.
author_facet Guzei, Ilia A.
Choudhary, Amit
Raines, Ronald T.
author_sort Guzei, Ilia A.
collection PubMed
description 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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spelling pubmed-36483252013-05-30 Pyramidalization of a carbonyl C atom in (2S)-N-(seleno­acet­yl)proline methyl ester Guzei, Ilia A. Choudhary, Amit Raines, Ronald T. Acta Crystallogr Sect E Struct Rep Online Organic Papers 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. International Union of Crystallography 2013-04-30 /pmc/articles/PMC3648325/ /pubmed/23723945 http://dx.doi.org/10.1107/S1600536813011112 Text en © Guzei et al. 2013 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
spellingShingle Organic Papers
Guzei, Ilia A.
Choudhary, Amit
Raines, Ronald T.
Pyramidalization of a carbonyl C atom in (2S)-N-(seleno­acet­yl)proline methyl ester
title Pyramidalization of a carbonyl C atom in (2S)-N-(seleno­acet­yl)proline methyl ester
title_full Pyramidalization of a carbonyl C atom in (2S)-N-(seleno­acet­yl)proline methyl ester
title_fullStr Pyramidalization of a carbonyl C atom in (2S)-N-(seleno­acet­yl)proline methyl ester
title_full_unstemmed Pyramidalization of a carbonyl C atom in (2S)-N-(seleno­acet­yl)proline methyl ester
title_short Pyramidalization of a carbonyl C atom in (2S)-N-(seleno­acet­yl)proline methyl ester
title_sort pyramidalization of a carbonyl c atom in (2s)-n-(seleno­acet­yl)proline methyl ester
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3648325/
https://www.ncbi.nlm.nih.gov/pubmed/23723945
http://dx.doi.org/10.1107/S1600536813011112
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