n→π* Interactions Engender Chirality in Carbonyl Groups | Zendy

Amit Choudhary | Zendy; Robert W. Newberry | Zendy; Ronald T. Raines | Zendy

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n→π* Interactions Engender Chirality in Carbonyl Groups

Author(s) -

Amit Choudhary,

Robert W. Newberry,

Ronald T. Raines

Publication year - 2014

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/ol5012967

Subject(s) - antibonding molecular orbital , delocalized electron , chemistry , diastereomer , chirality (physics) , electron delocalization , planar chirality , carbonyl group , group (periodic table) , stereochemistry , crystallography , electron , atomic orbital , organic chemistry , catalysis , enantioselective synthesis , physics , chiral symmetry , nambu–jona lasinio model , quantum mechanics , quark

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.

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