Cormanich Rodrigo A, Rittner Roberto, O'Hagan David, Bühl Michael
School of Chemistry, University of St Andrews, North Haugh, St Andrews, Fife KY169ST, United Kingdom.
Chemistry Institute, State University of Campinas, P.O. Box 6154, 13083-971, Campinas, SP, Brazil.
J Comput Chem. 2016 Jan 5;37(1):25-33. doi: 10.1002/jcc.23918. Epub 2015 Apr 23.
Weak inter- and intra- molecular C(δ+)F(δ-)···C(δ+)=O(δ-) interactions were theoretically evaluated in 4 different sets of compounds at different theoretical levels. Intermolecular CH3F···C=O interactions were stabilizing by about 1 kcal mol(-1) for various carbonyl containing functional groups. Intramolecular CF···C=O interactions were also detected in aliphatic and fluorinated cyclohexane carbonyl derivatives. However, the stabilization provided by intramolecular CF···C=O interactions was not enough to govern the conformational preferences of compounds 2-4.
在4组不同的化合物中，于不同理论水平对弱的分子间和分子内C(δ+)F(δ-)···C(δ+)=O(δ-)相互作用进行了理论评估。对于各种含羰基官能团，分子间CH3F···C=O相互作用的稳定化作用约为1 kcal mol(-1)。在脂肪族和氟化环己烷羰基衍生物中也检测到了分子内CF···C=O相互作用。然而，分子内CF···C=O相互作用提供的稳定化作用不足以决定化合物2 - 4的构象偏好。
