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Mesomeric and electromeric factors in the mononitronaphthylamines

Richards, J. H. and Walker, S. (1964) Mesomeric and electromeric factors in the mononitronaphthylamines. Tetrahedron, 20 (4). pp. 841-853. ISSN 0040-4020. https://resolver.caltech.edu/CaltechAUTHORS:20150429-091225034

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Abstract

The electric dipole moments of the ten mononitronaphthylamines with the substituents in non-adjacent positions and the 1-nitronaphthalene and 1-naphthylamine have now been completed in the solvents—benzene and dioxan. Interaction moments have been calculated for the mononitronaphthylamines in each solvent and linear relationship with these and the corresponding σ values ensue for the following substituent position (i) homonuclear (ii) heteronuclear in quinonoid positions (iii) heteronuclear in non-quinonoid positions. The homonuclear isomers exhibit similar features to the m- and p-nitroanilines. The isomers of type (ii) provide direct evidence for the existence of quinonoid resonance forms and in two cases at least their increased contribution in dioxan as opposed to benzene solution. In particular, 5-nitro-1-naphthylamine appears to have a negligible quinonoid contribution in benzene but quite appreciable in dioxan. Thus, the behaviour brings out the electromeric nature of the solute molecule by intermolecular hydrogen bonding with the solvent. This effect appears to be significant only when the substituents are in quinonoid positions. Apart from substituents in such positions and small deviations, the isomers obey the relationship obtained by Smith and Walshaw1 for various m- and p-substituted anilines.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1016/S0040-4020(01)98416-9DOIArticle
http://www.sciencedirect.com/science/article/pii/S0040402001984169PublisherArticle
Additional Information:© 1964 Pergamon Press Ltd. Received 6 December 1963, Available online 6 March 2001. We are indebted to the D.S.I.R. for an award (J.H.R.) and to Dr. E. R. Ward for supplying the nitronaphthylamines. We express our gratitude to Mr. L. P. Priestley, Head of the School of Chemistry, College of Technology, Leicester, where the practical work was carried out, and to Mr. A. Clarke for technical assistance.
Issue or Number:4
Record Number:CaltechAUTHORS:20150429-091225034
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20150429-091225034
Official Citation:J.H. Richards, S. Walker, Mesomeric and electromeric factors in the mononitronaphthylamines, Tetrahedron, Volume 20, Issue 4, 1964, Pages 841-853, ISSN 0040-4020, http://dx.doi.org/10.1016/S0040-4020(01)98416-9. (http://www.sciencedirect.com/science/article/pii/S0040402001984169)
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:57083
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:29 Apr 2015 16:40
Last Modified:03 Oct 2019 08:20

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