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Surfing the π-clouds for Non-covalent Interactions: A comparative Study of arenes versus Alkenes
| Title: | Surfing the π-clouds for Non-covalent Interactions: A comparative Study of arenes versus Alkenes |
| Authors: | Rzepa, HS E. Aliev, A R. Arendorf, J Ilias Pavlakos B. Moreno, R Michael J. Porter B. Motherwell, W |
| Item Type: | Dataset |
| Abstract: | A comparative study by dynamic NMR spectroscopy using molecular balances indicates that non-covalent functional group interactions with an arene dominate over those with an alkene with a p-facial intramolecular hydrogen bond from a hydroxyl group to an arene being favoured by 1.2 kJmol-1. The strongest interaction observed in this study is with the cyano group and analysis of the series Y= Et, CH=CH2, C≡CH and C≡N 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 dependences on the solvent hydrogen bond acceptor parameter β A comparative study by dynamic NMR spectroscopy using molecular balances indicates that non-covalent functional group interactions with an arene dominate over those with an alkene with a p-facial intramolecular hydrogen bond from a hydroxyl group to an arene being favoured by 1.2 kJmol-1. The strongest interaction observed in this study is with the cyano group and analysis of the series Y= Et, CH=CH2, C≡CH and C≡N 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 dependences on the solvent hydrogen bond acceptor parameter β A comparative study by dynamic NMR spectroscopy using molecular balances indicates that non-covalent functional group interactions with an arene dominate over those with an alkene with a p-facial intramolecular hydrogen bond from a hydroxyl group to an arene being favoured by 1.2 kJmol-1. The strongest interaction observed in this study is with the cyano group and analysis of the series Y= Et, CH=CH2, C≡CH and C≡N 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 dependences on the solvent hydrogen bond acceptor parameter β |
| Issue Date: | 11-Sep-2014 |
| URI: | http://hdl.handle.net/10044/1/30291 |
| DOI: | http://dx.doi.org/10.6084/m9.figshare.1167503 |
| Keywords: | nmr Computational Chemistry NMR Spectroscopy |
| Appears in Collections: | Faculty of Natural Sciences - Research Data |
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