title: Inter- and intramolecular CF···C=O interactions on aliphatic and cyclohexane carbonyl derivatives.
abstract: 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.
authors.affiliation: 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.
authors.forename: Rodrigo A
authors.initials: RA
authors.lastname: Cormanich
authors.affiliation: Chemistry Institute, State University of Campinas, P.O. Box 6154, 13083-971, Campinas, SP, Brazil.
authors.forename: Roberto
authors.initials: R
authors.lastname: Rittner
authors.affiliation: School of Chemistry, University of St Andrews, North Haugh, St Andrews, Fife KY169ST, United Kingdom.
authors.forename: David
authors.initials: D
authors.lastname: O'Hagan
authors.affiliation: School of Chemistry, University of St Andrews, North Haugh, St Andrews, Fife KY169ST, United Kingdom.
authors.forename: Michael
authors.initials: M
authors.lastname: Bühl
mesh_terms: D003510:Cyclohexanes / Q000737:chemistry*; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D011789:Quantum Theory
chemical_list: D003510:Cyclohexanes; D006845:Hydrocarbons, Fluorinated; D007659:Ketones; C506365:Cyclohexane
keywords: CF···CO interactions; organofluorine compounds; stereoelectronic effects