Issue 2, 2001
From the journal:

Journal of the Chemical Society, Perkin Transactions 2

Attractive and repulsive effects in the interactions between electron-rich and electron-deficient groups in peri-substituted naphthalenes

Jane O’Leary,a   Paul C. Bell,a   John D. Wallis*a  and  W. Bernd Schweizerb  

* Corresponding authors

a Department of Chemistry and Physics, The Nottingham Trent University, Clifton Lane, Nottingham, UK
E-mail: john.wallis@ntu.ac.uk

b Laboratorium für Organische Chemie, ETH Zentrum, Universitatstrasse 16, Zürich, Switzerland

Abstract

The 1,5 Me2N ⋯ C(sp2) separations in a series of peri-substituted naphthalene derivatives are sensitive to the through-space electron-attracting power of the carbon-containing functional group, while the corresponding MeO ⋯ C(sp2) separations are relatively insensitive in accord with the different nucleophilicities of the two groups. These separations are a balance between a steric effect and a covalent interaction, and from a comparison of the Me2N ⋯ C and MeO ⋯ C distances for a given functional group it is proposed that the Me2N ⋯ C interaction has an attractive component if the Me2N ⋯ C separation is less than ∼(MeO ⋯ C + 0.15) Å, the latter factor arising from the greater size of the bonded nitrogen atom.

Graphical abstract: Attractive and repulsive effects in the interactions between electron-rich and electron-deficient groups in peri-substituted naphthalenes

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Article information

DOI
https://doi.org/10.1039/B008226K
Article type
Paper
Submitted
12 Oct 2000
Accepted
07 Dec 2000
First published
12 Jan 2001

J. Chem. Soc., Perkin Trans. 2, 2001, 133-139

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Attractive and repulsive effects in the interactions between electron-rich and electron-deficient groups in peri-substituted naphthalenes

J. O’Leary, P. C. Bell, J. D. Wallis and W. B. Schweizer, J. Chem. Soc., Perkin Trans. 2, 2001, 133 DOI: 10.1039/B008226K

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