Ralf Haiges - On the Nature of C-H···F-C Interactions in Hindered CF3-C(sp3) Bond Rotations.

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  Publication Details (including relevant citation   information): Prakash, G. K. Surya, Wang, Fang, Rahm,   Martin, Shen, Jingguo, Ni, Chuanfa, Haiges, Ralf, Olah, George   A., Angew. Chem., Int. Ed., 2011,   50 (49), pp 11761-11764, S11761/1-S11761/93

  Abstract: In cinchona alkaloid-based scaffolds,   hindered CF3 rotations have been obsd. 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 chem. and exptl.   studies have shown that the noncovalent C3'-H1···F-C interactions   in the studied cases possess a weak hydrogen bonding-like   character. [on SciFinder(R)]

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