Skip to content

Research at St Andrews

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

Research output: Contribution to journalArticlepeer-review

DOI

Open Access permissions

Open

Author(s)

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

School/Research organisations

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.
Close

Details

Original languageEnglish
JournalPhysical Chemistry Chemical Physics
VolumeIn press
Early online date21 Oct 2015
DOIs
Publication statusPublished - 2015

Discover related content
Find related publications, people, projects and more using interactive charts.

View graph of relations

Related by author

  1. Janus face all-cis 1,2,4,5-tetrakis(trifluoromethyl)- and all-cis 1,2,3,4,5,6-hexakis(trifluoromethyl)- cyclohexanes

    Yu, C., Kütt, A., Röschenthaler, G-V., Lebl, T., Cordes, D. B., Slawin, A. M. Z., Buehl, M. & O'Hagan, D., 26 Oct 2020, In: Angewandte Chemie International Edition. 59, 45, p. 19905-19909 5 p.

    Research output: Contribution to journalArticlepeer-review

  2. Probing the helical integrity of multivicinal all-syn-fluoro alkanes

    Al-Maharik, N., Cordes, D. B., Slawin, A. M. Z., Buhl, M. & O'Hagan, D., 7 Feb 2020, In: Organic & Biomolecular Chemistry. 18, 5, p. 878-887 10 p.

    Research output: Contribution to journalArticlepeer-review

  3. Acetyl coenzyme A analogues as rationally designed inhibitors of citrate synthase

    Bello, D., Rubanu, M. G., Bandaranayaka, N., Götze, J. P., Bühl, M. & O'Hagan, D., 2 May 2019, In: ChemBioChem. 20, 9, p. 1174-1182

    Research output: Contribution to journalArticlepeer-review

  4. Benzylic functionalisation of phenyl all-cis-2, 3, 5, 6-tetrafluorocyclohexane provides access to new organofluorine building blocks

    Bykova, T., Al-Maharik, N., Slawin, A. M. Z., Buehl, M., Lebl, T. & O'Hagan, D., 31 Jul 2018, In: Chemistry - A European Journal. Early View

    Research output: Contribution to journalReview articlepeer-review

  5. Fluorinated cyclopropanes: Synthesis and chemistry of the aryl α,β,β-trifluorocyclopropane motif

    Thomson, C., Zhang, Q., Al-Maharik, N., Buehl, M., Cordes, D. B., Slawin, A. & O'Hagan, D., 3 Jul 2018, In: Chemical Communications. In press

    Research output: Contribution to journalArticlepeer-review

Related by journal

  1. Physical Chemistry Chemical Physics (Journal)

    Finlay Morrison (Reviewer)

    2009 → …

    Activity: Publication peer-review and editorial work typesPeer review of manuscripts

Related by journal

  1. A general model to optimise CuII labelling efficiency of double-histidine motifs for pulse dipolar EPR applications

    Wort, J., Ackermann, K., Norman, D. & Bode, B. E., 14 Feb 2021, In: Physical Chemistry Chemical Physics. 23, 6, p. 3810-3819 10 p.

    Research output: Contribution to journalArticlepeer-review

  2. A quinone based single-molecule switch as building block for molecular electronics

    Früchtl, H. A. & van Mourik, T., 21 Jan 2021, In: Physical Chemistry Chemical Physics. 23, 3, p. 1811-1814

    Research output: Contribution to journalArticlepeer-review

  3. The contribution of non-classical CHax∙∙∙OC hydrogen bonds to the anomeric effect in fluoro and oxa-methoxycyclohexanes

    Piscelli, B., O'Hagan, D. & Cormanich, R., 2 Mar 2021, In: Physical Chemistry Chemical Physics. 23, 10, p. 5845-5851

    Research output: Contribution to journalArticlepeer-review

  4. Effects of crystal size on methanol to hydrocarbon conversion over single crystals of ZSM-5 studied by synchrotron infrared microspectroscopy

    Minova, I. B., Matam, S. K., Greenaway, A., Catlow, C. R. A., Frogley, M. D., Cinque, G., Wright, P. A. & Howe, R. F., 14 Sep 2020, In: Physical chemistry chemical physics : PCCP. 22, 34, p. 18849-18859 11 p.

    Research output: Contribution to journalArticlepeer-review

  5. Following the unusual breathing behaviour of 17O-enriched mixed-metal (Al,Ga)-MIL-53 using NMR crystallography

    Rice, C. M., Davis, Z. H., McKay, D., Bignami, G. P. M., Chitac, R. G., Dawson, D. M., Morris, R. E. & Ashbrook, S. E., 14 Jul 2020, In: Physical Chemistry Chemical Physics. 22, 26, p. 14514-14526 13 p.

    Research output: Contribution to journalArticlepeer-review

ID: 225349194

Top