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On the Nature of CH⋅⋅⋅FC Interactions in Hindered CF 3 C(sp 3 ) Bond Rotations
Author(s) -
Prakash G. K. Surya,
Wang Fang,
Rahm Martin,
Shen Jingguo,
Ni Chuanfa,
Haiges Ralf,
Olah George A.
Publication year - 2011
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/anie.201105288
Subject(s) - non covalent interactions , hydrogen bond , quantum chemical , cinchona , character (mathematics) , chemistry , content (measure theory) , computational chemistry , organic chemistry , mathematics , molecule , catalysis , mathematical analysis , geometry , enantioselective synthesis
In cinchona alkaloid‐based scaffolds , hindered CF 3 rotations have been observed. The variation in barrier heights for the CF 3 rotations is controlled by the corresponding entropic changes when the substituents are changed from an allyl to a bulky 9‐methylanthracenyl group. Quantum chemical and experimental studies have shown that the noncovalent C3′H1⋅⋅⋅FC interactions in the studied cases possess a weak hydrogen bonding‐like character.