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

Rodrigo Cormanich; Neil Steven Keddie; Roberto Rittner; David O'Hagan; Michael Buehl

doi:10.1039/C5CP04537A

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

Rodrigo Cormanich, Neil Steven Keddie, Roberto Rittner, David O'Hagan, Michael Buehl

Research output: Contribution to journal › Article › peer-review

Abstract

We present the first high-level ab initio benchmark study of the interaction energy between fluorocyclohexanes and benzene. These compounds form CH...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 and -6.4 kcal/mol 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.

Original language	English
Journal	Physical Chemistry Chemical Physics
Volume	In press
Early online date	21 Oct 2015
DOIs	https://doi.org/10.1039/C5CP04537A
Publication status	Published - 2015

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Buehl_2015_PCCP_Particularly_AM
Copyright 2015 the Authors. This work is made available online in accordance with the publisher’s policies. This is the author created, accepted version manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at https://dx.doi.org/10.1039/C5CP04537A
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title = "Particularly strong C-H...pi interactions between benzene and all-cis 1,2,3,4,5,6-hexafluorocyclohexane",

abstract = "We present the first high-level ab initio benchmark study of the interaction energy between fluorocyclohexanes and benzene. These compounds form CH...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 and -6.4 kcal/mol 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.",

author = "Rodrigo Cormanich and Keddie, {Neil Steven} and Roberto Rittner and David O'Hagan and Michael Buehl",

note = "The authors thank EaStCHEM and the University of St Andrews for access to a computing facility managed by Dr H. Fruchtl, CNPq and FAPESP for the studentship for R.A.C. (#2011/01170-1, FAPESP) and for financial support (#2014/25903-6), as well as CNPq for the fellowship for R.R. DO{\textquoteright}H thanks the Royal Society for a Wolfson Research Merit Award. ",

year = "2015",

doi = "10.1039/C5CP04537A",

language = "English",

volume = "In press",

journal = "Physical Chemistry Chemical Physics",

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T1 - Particularly strong C-H...pi interactions between benzene and all-cis 1,2,3,4,5,6-hexafluorocyclohexane

AU - Cormanich, Rodrigo

AU - Keddie, Neil Steven

AU - Rittner, Roberto

AU - O'Hagan, David

AU - Buehl, Michael

N1 - The authors thank EaStCHEM and the University of St Andrews for access to a computing facility managed by Dr H. Fruchtl, CNPq and FAPESP for the studentship for R.A.C. (#2011/01170-1, FAPESP) and for financial support (#2014/25903-6), as well as CNPq for the fellowship for R.R. DO’H thanks the Royal Society for a Wolfson Research Merit Award.

PY - 2015

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N2 - We present the first high-level ab initio benchmark study of the interaction energy between fluorocyclohexanes and benzene. These compounds form CH...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 and -6.4 kcal/mol 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.

AB - We present the first high-level ab initio benchmark study of the interaction energy between fluorocyclohexanes and benzene. These compounds form CH...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 and -6.4 kcal/mol 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.

UR - http://www.rsc.org/suppdata/c5/cp/c5cp04537a/c5cp04537a1.pdf

U2 - 10.1039/C5CP04537A

DO - 10.1039/C5CP04537A

M3 - Article

SN - 1463-9076

VL - In press

JO - Physical Chemistry Chemical Physics

JF - Physical Chemistry Chemical Physics

ER -

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

Abstract

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Multivicinal fluorinated cyclohexanes: Multivicinal fluorinated cyclohexanes, a new structural motif in organic chemistry

Synthesis and properties of novel sequen: Synthesis and properties of novel sequentially fluorinated motifs in organcic chemistry

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

Abstract

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Projects

Multivicinal fluorinated cyclohexanes: Multivicinal fluorinated cyclohexanes, a new structural motif in organic chemistry

Synthesis and properties of novel sequen: Synthesis and properties of novel sequentially fluorinated motifs in organcic chemistry

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