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Issue 9, 2002
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The structure, modelling and dynamics of 2,7-diisopropoxy-1,8-diarylnaphthalenes

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Abstract

2,7-Diisopropoxy-1,8-dibromonaphthalene 5 was prepared in two steps from 2,7-dihydroxynaphthalene and was coupled under Suzuki cross-coupling conditions with boronic acids 9 and 10 to provide the corresponding 1,8-diarylnaphthalene systems 12a and 13a respectively. In contrast, attempted coupling of dibromide 5 with o-tolylboronic acid 11 proved unrewarding. Single crystal X-ray structure determination of compounds 12a and 13a showed that both structures possessed a high degree of structural deformation due to high internal steric repulsions between the 1,8-diaryl rings and their substituents. Dynamic 1H NMR experiments showed that these two systems possessed very slow phenylnaphthalene bond rotation (ca. 2 s−1), corresponding to rotation barriers (ΔG*) of 16–18 kcal mol−1. Molecular modelling predicts that such systems have approximately similar rotation barriers and that in order to completely prevent phenylnaphthalene bond rotation, an ortho-phenyl substituent is required, with a barrier to rotation of ca. 40 kcal mol−1.

Graphical abstract: The structure, modelling and dynamics of 2,7-diisopropoxy-1,8-diarylnaphthalenes

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Article information


Submitted
04 Feb 2002
Accepted
12 Jul 2002
First published
30 Jul 2002

J. Chem. Soc., Perkin Trans. 2, 2002, 1510-1519
Article type
Paper

The structure, modelling and dynamics of 2,7-diisopropoxy-1,8-diarylnaphthalenes

C. Thirsk, G. E. Hawkes, R. T. Kroemer, K. R. Liedl, T. Loerting, R. Nasser, R. G. Pritchard, M. Steele, J. E. Warren and A. Whiting*, J. Chem. Soc., Perkin Trans. 2, 2002, 1510
DOI: 10.1039/B201235A

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