Accounts of Chemical Research
Accounts of Chemical Research
5 years ago

The n→π* Interaction

The n→π* Interaction
Ronald T. Raines, Robert W. Newberry
The carbonyl group holds a prominent position in chemistry and biology not only because it allows diverse transformations but also because it supports key intermolecular interactions, including hydrogen bonding. More recently, carbonyl groups have been found to interact with a variety of nucleophiles, including other carbonyl groups, in what we have termed an n→π* interaction. In an n→π* interaction, a nucleophile donates lone-pair (n) electron density into the empty π* orbital of a nearby carbonyl group. Mixing of these orbitals releases energy, resulting in an attractive interaction. Hints of such interactions were evident in small-molecule crystal structures as early as the 1970s, but not until 2001 was the role of such interactions articulated clearly.

Publisher URL: http://dx.doi.org/10.1021/acs.accounts.7b00121

DOI: 10.1021/acs.accounts.7b00121

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