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

J Org Chem
Authors
Keywords
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.

Year of Publication
2011
Journal
J Org Chem
Volume
76
Issue
19
Pages
7933-7
Date Published
2011 Oct 07
ISSN
1520-6904
DOI
10.1021/jo201389d
PubMed ID
21842865
PubMed Central ID
PMC3184772
Links
Grant list
R01 AR044276 / AR / NIAMS NIH HHS / United States
R01 AR044276-16 / AR / NIAMS NIH HHS / United States