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Surfing the π-clouds for Non-covalent Interactions: A comparative Study of Arenes versus Alkenes

Aliev, AE; Arendorf, JRT; Pavlakos, I; Moreno, RB; Porter, MJ; Rzepa, HS; Motherwell, W; (2015) Surfing the π-clouds for Non-covalent Interactions: A comparative Study of Arenes versus Alkenes. Angewandte Chemie International Edition , 54 (2) pp. 551-555. 10.1002/anie.201409672. Green open access

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Abstract

A comparative study by NMR spectroscopy using molecular balances indicates that non-covalent functional group interactions with an arene dominate over those with an alkene and a p-facial intramolecular hydrogen bond from a hydroxyl group to an arene is favoured by ~1.2 kJ mol-1. The strongest interaction observed in this study is with the cyano group and analysis of the series of Et, CH=CH2, C≡CH and C≡N groups is indicative of a weak long range electrostatic interaction and a correlation with the electrophilicity of the Ca atom of the Y substituent. Changes in the free energy differences of conformers show a linear dependence on the solvent hydrogen bond acceptor parameter β.

Type: Article
Title: Surfing the π-clouds for Non-covalent Interactions: A comparative Study of Arenes versus Alkenes
Open access status: An open access version is available from UCL Discovery
DOI: 10.1002/anie.201409672
Publisher version: http://dx.doi.org/10.1002/anie.201409672
Language: English
Additional information: © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. This is the pre-peer reviewed version of the following article Aliev, A. E., Arendorf, J. R. T., Pavlakos, I., Moreno, R. B., Porter, M. J., Rzepa, H. S. and Motherwell, W. B. (2015), Surfing π Clouds for Noncovalent Interactions: Arenes versus Alkenes. Angew. Chem. Int. Ed., 54: 551–555. whcih hjas been published at http://dx.doi.org/10.1002/anie.201409672
UCL classification: UCL
UCL > Provost and Vice Provost Offices
UCL > Provost and Vice Provost Offices > UCL BEAMS
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences > Dept of Chemistry
URI: https://discovery.ucl.ac.uk/id/eprint/1455546
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