Models for incomplete nucleophilic attack on a protonated carbonyl group and electron-deficient alkenes: salts and zwitterions from 1-dimethylamino-naphthalene-8-carbaldehyde
Lari, A, Pitak, Mateusz, Coles, Simon J., Rees, Gethin, Day, S.P., Smith , M.E., Hanna, J.V. and Wallis, J.D. (2012) Models for incomplete nucleophilic attack on a protonated carbonyl group and electron-deficient alkenes: salts and zwitterions from 1-dimethylamino-naphthalene-8-carbaldehyde. Organic & Biomolecular Chemistry, 10, (38), 7763-7779. (doi:10.1039/C2OB25929J ).
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Description/Abstract
The X-ray crystal structures of salts and zwitterionic Knoevenagel products from 1-dimethylamino-naphthalene-8-carbaldehyde show long N-C bonds between peri-groups which provide models for incomplete nucleophilic attack on a protonated carbonyl group and electron-deficient alkenes respectively. For the salts the N-C bonds lie in the range 1.625-1.638 angstrom with C-OH bonds intermediate in length between single and double bonds, while for the zwitterions the N-C bonds lie in the range 1.612-1.660 angstrom. The structural assignment of the former is supported by solid state C-13 and N-15 NMR studies on doubly isotopically-labelled material. Several zwitterions were converted to naphtha[1,8-bc]azepines by a mechanism involving the tertiary amino effect.
| Item Type: | Article |
|---|---|
| ISSNs: | 1477-0520 (print) 1477-0539 (electronic) |
| Related URLs: | |
| Subjects: | Q Science > QD Chemistry |
| Divisions: | Faculty of Natural and Environmental Sciences Faculty of Natural and Environmental Sciences > Chemistry Faculty of Natural and Environmental Sciences > Chemistry > Molecular Assembly, Function & Structure |
| Item ID: | 345863 |
| Date Deposited: | 04 Dec 2012 17:35 |
| Last Modified: | 04 Dec 2012 17:35 |
| Contributors: | Lari, A (Author) Pitak, Mateusz (Author) Coles, Simon J. (Author) Rees, Gethin (Author) Day, S.P. (Author) Smith , M.E. (Author) Hanna, J.V. (Author) Wallis, J.D. (Author) |
| Date: | 2012 |
| Status: | Published |
| URI: | http://eprints.soton.ac.uk/id/eprint/345863 |
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