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)
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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
ePrint ID: 345863
Date Deposited: 04 Dec 2012 17:35
Last Modified: 27 Mar 2014 20:27
URI: http://eprints.soton.ac.uk/id/eprint/345863

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