Aliev, AE;
Pavlakos, I;
Arif, T;
Aliev, AE;
Motherwell, WB;
Tizzard, GJ;
Coles, SJ;
(2015)
Noncovalent Lone Pair⋅⋅⋅(No-π!)-Heteroarene Interactions: The Janus-Faced Hydroxy Group.
Angewandte Chemie International Edition
, 54
(28)
pp. 8169-8174.
10.1002/anie.201502103.
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Abstract
A comparative study by NMR using designed top pan molecular balances demonstrates that the noncovalent interaction of a hydroxyl group with π-deficient pyrazine and quinoxaline units involves a lone pair•••heteroarene interaction which is much stronger and essentially solvent independent when measured relative to the classical π-facial hydrogen bond to a benzene ring. Alkyl fluorides also prefer the heteroarene rings over the benzene ring. The attractive interaction between a quinoxaline and a terminal alkyne is also stronger than the intramolecular hydrogen bond to an arene.
| Type: | Article |
|---|---|
| Title: | Noncovalent Lone Pair⋅⋅⋅(No-π!)-Heteroarene Interactions: The Janus-Faced Hydroxy Group |
| Location: | Switzerland |
| Open access status: | An open access version is available from UCL Discovery |
| DOI: | 10.1002/anie.201502103 |
| Publisher version: | http://dx.doi.org/10.1002/anie.201502103 |
| Language: | English |
| Additional information: | This is the peer reviewed version of the following article: Aliev, AE; Pavlakos, I; Arif, T; Aliev, AE; Motherwell, WB; Tizzard, GJ; Coles, SJ; (2015) Noncovalent Lone Pair⋅⋅⋅(No-π!)-Heteroarene Interactions: The Janus-Faced Hydroxy Group. Angewandte Chemie International Edition , 54 (28) pp. 8169-8174. 10.1002/anie.201502103, which has been published in final form at http://dx.doi.org10.1002/anie.201502103. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving. |
| UCL classification: | UCL 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/1466630 |
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