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Issue 12, 2018
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Halocarbons as hydrogen bond acceptors: a spectroscopic study of haloethylbenzenes (PhCH2CH2X, X = F, Cl, Br) and their hydrate clusters

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Abstract

The electronic spectra of 2-bromoethylbenzene and its chloro and fluoro analogues have been recorded by resonant two-photon ionisation (R2PI) spectroscopy. Anti and gauche conformers have been assigned by rotational band contour analysis and IR-UV ion depletion spectroscopy in the CH region. Hydrate clusters of the anti conformers have also been observed, allowing the role of halocarbons as hydrogen bond acceptors to be examined in this context. The donor OH stretch of water bound to chlorine is red-shifted by 36 cm−1, or 39 cm−1 in the case of bromine. Although classed as weak H-bond acceptors, halocarbons are favourable acceptor sites compared to π systems. Fluorine stands out as the weakest H-bond acceptor amongst the halogens. Chlorine and bromine are also weak H-bond acceptors, but allow for more geometric lability, facilitating complimentary secondary interactions within the host molecule. Ab initio and DFT quantum chemical calculations, both harmonic and anharmonic, aid the structural assignments and analysis.

Graphical abstract: Halocarbons as hydrogen bond acceptors: a spectroscopic study of haloethylbenzenes (PhCH2CH2X, X = F, Cl, Br) and their hydrate clusters

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Publication details

The article was received on 31 Oct 2017, accepted on 04 Mar 2018 and first published on 05 Mar 2018


Article type: Paper
DOI: 10.1039/C7CP07365H
Citation: Phys. Chem. Chem. Phys., 2018,20, 8218-8227
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    Halocarbons as hydrogen bond acceptors: a spectroscopic study of haloethylbenzenes (PhCH2CH2X, X = F, Cl, Br) and their hydrate clusters

    P. A. Robertson, L. Villani, U. L. M. Dissanayake, L. F. Duncan, B. M. Abbott, D. J. D. Wilson and E. G. Robertson, Phys. Chem. Chem. Phys., 2018, 20, 8218
    DOI: 10.1039/C7CP07365H

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