Related Experiment Video
Updated: Apr 14, 2026

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
Inter- and intramolecular CF···C=O interactions on aliphatic and cyclohexane carbonyl derivatives
Rodrigo A Cormanich1,2, Roberto Rittner2, David O'Hagan1
1School of Chemistry, University of St Andrews, North Haugh, St Andrews, Fife KY169ST, United Kingdom.
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.
Related Concept Videos
Stability of Substituted Cyclohexanes
The two chair conformations of cyclohexanes undergo rapid interconversion at room temperature. Both forms have identical energies and stabilities, each comprising equal amounts of the equilibrium mixture. Replacing a hydrogen atom with a functional group makes the two conformations energetically non-equivalent.
For example, in...
Intramolecular Aldol Reaction
Radical Reactivity: Intramolecular vs Intermolecular
Chair Conformation of Cyclohexane
The hydrogen atoms linked to carbons are arranged in two different axial and equatorial orientations to achieve this...
Disubstituted Cyclohexanes: cis-trans Isomerism
In cyclohexane, the substituents can occupy different positions generating distinct isomers....
Conformations of Cycloalkanes

