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J Org Chem. 2011 Oct 7;76(19):7933-7. doi: 10.1021/jo201389d. Epub 2011 Sep 6.

An n→π* interaction in aspirin: implications for structure and reactivity.

Author information

1
Graduate Program in Biophysics, University of Wisconsin-Madison, Madison, Wisconsin 53706, United States.

Abstract

Stereoelectronic effects modulate molecular structure, reactivity, and conformation. We find that the interaction between the ester and carboxyl moieties of aspirin has a previously unappreciated quantum mechanical character that arises from the delocalization of an electron pair (n) of a donor group into the antibonding orbital (π*) of an acceptor group. This interaction affects the physicochemical attributes of aspirin and could have implications for its pharmacology.

PMID:
21842865
PMCID:
PMC3184772
DOI:
10.1021/jo201389d
[Indexed for MEDLINE]
Free PMC Article

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