On the Nature of C-H⋅⋅⋅F-C Interactions in Hindered CF3-C(sp3) Bond Rotations
Artikel i vetenskaplig tidskrift, 2011
In cinchona alkaloid-based scaffolds, hindered CF3 rotations have been observed. The variation in barrier heights for the CF3 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′[BOND]H1⋅⋅⋅F[BOND]C interactions in the studied cases possess a weak hydrogen bonding-like
hydrogen bonding
cinchona alkaloids
steric hindrance
conformational isomerism
fluorine
Författare
G. K. Surya Prakash
F. Wang
Martin Rahm
Jingguo Shen
Chuanfa Ni
Ralf Haiges
George A. Olah
Angewandte Chemie - International Edition
1433-7851 (ISSN) 1521-3773 (eISSN)
Vol. 50 49 11761-11764, S11761/1-S11761/93-Ämneskategorier
Teoretisk kemi
Organisk kemi
DOI
10.1002/anie.201105288