title: An n→π* interaction in aspirin: implications for structure and reactivity.
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.
authors.affiliation: Graduate Program in Biophysics, University of Wisconsin-Madison, Madison, Wisconsin 53706, United States.
authors.forename: Amit
authors.initials: A
authors.lastname: Choudhary
authors.forename: Kimberli J
authors.initials: KJ
authors.lastname: Kamer
authors.forename: Ronald T
authors.initials: RT
authors.lastname: Raines
mesh_terms: D001241:Aspirin / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D055585:Physical Phenomena
chemical_list: D001241:Aspirin