Reactions and interactions between peri-groups in 1-dimethylamino-naphthalene salts: an example of a 'through space' amide

Wannebroucq, A., Jarmyn, A.P., Pitak, M.B., Coles, S.J. and Wallis, J.D. ORCID: 0000-0001-7259-8783, 2016. Reactions and interactions between peri-groups in 1-dimethylamino-naphthalene salts: an example of a 'through space' amide. Pure & Applied Chemistry, 88 (4), pp. 317-331. ISSN 1365-3075

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Abstract

8-Dimethylaminonaphthalene-1-carbaldehyde reacts readily at 0°C with benzoyl or pivaloyl chloride by O-acylation and formation of a N–C bond (1.566(2)–1.568(3) Å) between the peri-substituents to give a salt. The reaction is promoted by electron donation from the dimethylamino group to the carbonyl group, akin to the properties of an amide. In contrast, the corresponding methyl ester and N,N-diisopropylamide react with acid in ether by protonation of the dimethylamino group and formation of a hydrogen bond to the carbonyl group, while under similar conditions the N,N-dimethylamide undergoes ready hydrolysis to the acid. The structures of products are determined by X-ray crystallography, and from the latter hydrolysis crystals containing zwitterionic 1-dimethylammonium-naphthalene-8-carboxylate and the corresponding O-protonated cation along with dimethylammonium and triflate ions were obtained.

Item Type: Journal article
Publication Title: Pure & Applied Chemistry
Creators: Wannebroucq, A., Jarmyn, A.P., Pitak, M.B., Coles, S.J. and Wallis, J.D.
Publisher: Walter De Gruyter
Date: 1 April 2016
Volume: 88
Number: 4
ISSN: 1365-3075
Divisions: Schools > School of Science and Technology
Depositing User: Linda Sullivan
Date Added: 20 Jul 2016 11:36
Last Modified: 10 Oct 2017 13:22
URI: http://irep.ntu.ac.uk/id/eprint/28160

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