n→π* Interactions Engender Chirality in Carbonyl Groups

[Image: see text] An n→π* interaction stems from the delocalization of the electron pair (n) of a donor group into the antibonding orbital (π*) of a carbonyl group. Crystallographic analyses of five pairs of diastereoisomers demonstrate that an n→π* interaction can induce chirality in an otherwise p...

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Autores principales: Choudhary, Amit, Newberry, Robert W., Raines, Ronald T.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4096190/
https://www.ncbi.nlm.nih.gov/pubmed/24926562
http://dx.doi.org/10.1021/ol5012967
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author Choudhary, Amit
Newberry, Robert W.
Raines, Ronald T.
author_facet Choudhary, Amit
Newberry, Robert W.
Raines, Ronald T.
author_sort Choudhary, Amit
collection PubMed
description [Image: see text] An n→π* interaction stems from the delocalization of the electron pair (n) of a donor group into the antibonding orbital (π*) of a carbonyl group. Crystallographic analyses of five pairs of diastereoisomers demonstrate that an n→π* interaction can induce chirality in an otherwise planar, prochiral carbonyl group. Thus, a subtle delocalization of electrons can have stereochemical consequences.
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spelling pubmed-40961902015-06-13 n→π* Interactions Engender Chirality in Carbonyl Groups Choudhary, Amit Newberry, Robert W. Raines, Ronald T. Org Lett [Image: see text] An n→π* interaction stems from the delocalization of the electron pair (n) of a donor group into the antibonding orbital (π*) of a carbonyl group. Crystallographic analyses of five pairs of diastereoisomers demonstrate that an n→π* interaction can induce chirality in an otherwise planar, prochiral carbonyl group. Thus, a subtle delocalization of electrons can have stereochemical consequences. American Chemical Society 2014-06-13 2014-07-03 /pmc/articles/PMC4096190/ /pubmed/24926562 http://dx.doi.org/10.1021/ol5012967 Text en Copyright © 2014 American Chemical Society Terms of Use (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html)
spellingShingle Choudhary, Amit
Newberry, Robert W.
Raines, Ronald T.
n→π* Interactions Engender Chirality in Carbonyl Groups
title n→π* Interactions Engender Chirality in Carbonyl Groups
title_full n→π* Interactions Engender Chirality in Carbonyl Groups
title_fullStr n→π* Interactions Engender Chirality in Carbonyl Groups
title_full_unstemmed n→π* Interactions Engender Chirality in Carbonyl Groups
title_short n→π* Interactions Engender Chirality in Carbonyl Groups
title_sort n→π* interactions engender chirality in carbonyl groups
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4096190/
https://www.ncbi.nlm.nih.gov/pubmed/24926562
http://dx.doi.org/10.1021/ol5012967
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