13C NMR spectroscopic studies of C-nitroso compounds. The orientation of the nitroso group in substituted nitrosobenzenes

Brian G. Gowenlock, Mailer Cameron, Alan S F Boyd, Baheeja M. Al-Tahou, Paul McKenna

Research output: Contribution to journalArticle

Abstract

The carbon-13 chemical shifts of several substituted nitrosobenzenes are reported. It is shown that the NO group can be orientated to lie in the plane of the ring when constrained either by a bulky ortho substituent or in the solid state. In the presence of 2.6-di-tert-butyl substituents the NO group is twisted into orthogonality with the ring. The changes in the 13C chemical shifts are larger for the NO group than for other functional groups. It is suggested that these effects are a consequence of the electronic character of the NO group and that the nitrogen lone pair of electrons is of fundamental importance in producing these unique effects. The dimeric nitroso functional group does not display these properties.

Original languageEnglish
Pages (from-to)514-518
Number of pages5
JournalCanadian Journal of Chemistry
Volume72
Issue number3
Publication statusPublished - Mar 1994

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