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Metal-assisted reactions. Part 29. Structure and hydrogenolysis of C-N bonds in derivatives of aromatic amines. Bond length and electronegativity changes from X-ray crystallographic data

Lookup NU author(s): Professor William Clegg

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Abstract

Pseudosaccharyl and phenyltetrazolyl derivatives 1-6 were prepared with the aim of weakening the originally strong C-N bond in aromatic amines and facilitating its hydrogenolysis. Structural analyses of the amines 1-6 by H-1 and C-13 NMR spectroscopy and X-ray diffraction methods have revealed major changes in C-N bond lengths on derivatization as a result of changes in conjugation. These changes are discussed in relation to the observed reactivity of compounds 1-6 towards catalytic and non-catalytic C-N bond hydrogenolysis.

Publication metadata

Author(s): Brigas AF, Clegg W, Dillon CJ, Fonseca CFC, Johnstone RAW

Publication type: Article

Publication status: Published

Journal: Journal of the Royal Chemical Society: Perkin Transactions 2

Year: 2001

Issue: 8

Pages: 1315-1324

ISSN (print): 1472-779X

ISSN (electronic): 1364-5471

Publisher: Royal Society of Chemistry

URL: http://dx.doi.org/10.1039/b102571f

DOI: 10.1039/b102571f

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