An n??* interaction in aspirin: implications for structure and reactivity.
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ABSTRACT:
SUBMITTER: Choudhary A
PROVIDER: S-EPMC3184772 | biostudies-literature | 2011 Oct
REPOSITORIES: biostudies-literature
Publications
An n→π* interaction in aspirin: implications for structure and reactivity.
Choudhary Amit A Kamer Kimberli J KJ Raines Ronald T RT
The Journal of organic chemistry 20110906 19
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. ...[more]
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