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Unusual C−H⋅⋅⋅Se=C Interactions in Aldols of Chiral N ‐Acyl Selones Detected by Gradient‐Selected 1 H– 77 Se HMQC NMR Spectroscopy and X‐ray Crystallography
Author(s) -
Michalczyk Ryszard,
Schmidt Jürgen G.,
Moody Eddie,
Li Zizhong,
Wu Ruilian,
Dunlap R. Bruce,
Odom Jerome D.,
Silks III Louis A. “Pete”
Publication year - 2000
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/1521-3773(20000901)39:17<3067::aid-anie3067>3.0.co;2-d
Subject(s) - chemistry , nuclear magnetic resonance spectroscopy , crystallography , hydrogen bond , spectroscopy , stereochemistry , molecule , organic chemistry , physics , quantum mechanics
A fundamental new type of non‐opportunistic hydrogen bond was detected between a proximal C−H group and the selenium atom of a selenocarbonyl group in aldols of chiral N ‐acyl selones (see structure) by gradient‐selected 1 H– 77 Se HMQC NMR spectroscopy and X‐ray crystallography. The C−H⋅⋅⋅Se=C interaction provides a possible explanation for the ability of chiral selone groups to interrogate remotely disposed chiral centers by 77 Se NMR spectroscopy.