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Bristow, JC, Naftalin, I, Cliff, SVA, Yang, S, Carravetta, M, Heinmaa, I, Stern, R and Wallis, JD 
ORCID: https://orcid.org/0000-0001-7259-8783,
2020.
Modelling of an aza-Michael reaction from crystalline naphthalene derivatives containing peri–peri interactions: very long N–C bonds?
CrystEngComm.
ISSN 1466-8033
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Abstract
The separation between a pair of peri-located dimethylamino and ethene-2,2-dinitrile groups in a naphthalene molecule, which models the progress of a Michael reaction, can be controlled by the installation of a short ethylene bridge or the introduction of repulsive interactions at the opposite set of peri positions. Introduction of a dimethylammonium substituent produced a hydrated chloride salt in which the Me2N⋯C(H)[double bond, length as m-dash]C(CN)2 separation between reactive groups decreases, reversibly, from 2.167 Å at 200 K to 1.749 Å at 100 K, with the maximum rate of change in the range 128–140 K, which was studied by variable temperature X-ray crystallography and solid state NMR. From these and other crystallographic data a correlation between Me2N⋯C bond formation and alkene bond breaking was constructed for the first step of an aza-Michael reaction.
| Item Type: | Journal article |
|---|---|
| Publication Title: | CrystEngComm |
| Creators: | Bristow, J.C., Naftalin, I., Cliff, S.V.A., Yang, S., Carravetta, M., Heinmaa, I., Stern, R. and Wallis, J.D. |
| Publisher: | Royal Society of Chemistry (RSC) |
| Date: | 17 September 2020 |
| ISSN: | 1466-8033 |
| Identifiers: | Number Type 10.1039/d0ce01137a DOI 1371342 Other |
| Rights: | This journal is © The Royal Society of Chemistry 2020. Open Access Article. Published on 17 September 2020. Downloaded on 9/30/2020 1:39:26 PM. This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. |
| Divisions: | Schools > School of Science and Technology |
| Record created by: | Linda Sullivan |
| Date Added: | 02 Oct 2020 10:07 |
| Last Modified: | 31 May 2021 15:15 |
| URI: | https://irep.ntu.ac.uk/id/eprint/41100 |
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