Particularly strong C-H center dot center dot center dot pi interactions between benzene and all-cis 1,2,3,4,5,6-hexafluorocyclohexane

Author(s)

Cormanich, Rodrigo A. ^{[1, 2]} ; Keddie, Neil S. ^[2] ; Rittner, Roberto ^[1] ; O'Hagan, David ^[2] ; Buehl, Michael ^[2]

Affiliation

^[1] Univ Estadual Campinas, Inst Chem, BR-13083970 Campinas, SP - Brazil

^[2] Univ St Andrews, EastChem Sch Chem, St Andrews KY16 95T, Fife - Scotland

• Document type: Journal article
• Source: Physical Chemistry Chemical Physics; v. 17, n. 44, p. 29475-29478, 2015.
• Web of Science Citations: 10

Abstract

We present the first high-level ab initio benchmark study of the interaction energy between fluorocyclohexanes and benzene. These compounds form CH center dot center dot center dot pi interactions with aromatic solvents which causes notable shielding of the axial cyclohexane protons. For the recently synthesised all-cis 1,2,3,4,5,6-hexafluorocyclohexane the interaction energy with benzene amounts to -7.9 kcal mol(-1) and -6.4 kcal mol(-1) at the MP2 and SCS-MP2 levels, respectively (extrapolated to the complete basis set limit), which according to dispersion-corrected density functional calculations, is largely due to dispersion. (AU)

• FAPESP's process: 11/01170-1 - Physicochemical studies of organic compounds: long range inractions and conformational analysis of organofluorine compounds.
• Grantee: Rodrigo Antonio Cormanich
• Support Opportunities: Scholarships in Brazil - Doctorate
• FAPESP's process: 14/25903-6 - Molecular structure of some amino acids and dipeptides
• Grantee: Roberto Rittner Neto
• Support Opportunities: Regular Research Grants