Choudhary Amit, Newberry Robert W, Raines Ronald T
Graduate Program in Biophysics and Departments of ‡Chemistry and §Biochemistry, University of Wisconsin-Madison , Madison, Wisconsin 53706, United States.
Org Lett. 2014 Jul 3;16(13):3421-3. doi: 10.1021/ol5012967. Epub 2014 Jun 13.
An n→π* interaction stems from the delocalization of the electron pair (n) of a donor group into the antibonding orbital (π*) of a carbonyl group. Crystallographic analyses of five pairs of diastereoisomers demonstrate that an n→π* interaction can induce chirality in an otherwise planar, prochiral carbonyl group. Thus, a subtle delocalization of electrons can have stereochemical consequences.
n→π相互作用源于供体基团的电子对（n）离域到羰基的反键轨道（π）中。对五对对映异构体的晶体学分析表明，n→π*相互作用可在原本平面的前手性羰基中诱导手性。因此，电子的微妙离域可产生立体化学后果。
