An n→π* interaction in aspirin: implications for structure and reactivity.
J Org Chem
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| 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 (Ï€*) of an acceptor group. This interaction affects the physicochemical attributes of aspirin and could have implications for its pharmacology. |
| Year of Publication | 2011
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| Journal | J Org Chem
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| Volume | 76
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| Issue | 19
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| Pages | 7933-7
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| Date Published | 2011 Oct 07
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| ISSN | 1520-6904
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| DOI | 10.1021/jo201389d
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| PubMed ID | 21842865
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| PubMed Central ID | PMC3184772
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| Grant list | R01 AR044276 / AR / NIAMS NIH HHS / United States
R01 AR044276-16 / AR / NIAMS NIH HHS / United States
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