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Issue 0, 1986
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Isatogens: crystal structure, electron density calculations, and 13C nuclear magnetic resonance spectra

Abstract

The structures of 2-phenylisatogen (1a) and 2-(2-pyridyl)isatogen (1b) have been determined by X-ray crystallography. In 2-phenylisatogen the isatogen ring and the phenyl ring are almost fully co-planar. In contrast there is a dihedral angle of 45.5° between the isatogen ring and the 2-pyridyl ring in 2-(2-pyridyl)isatogen. The nitrogen atoms in the two ring systems are in a transoid relationship. Non-bonded separation distances in both compounds suggest strong dipolar associations involving the N–O bonds. MNDO Calculations using the experimental geometries of these two compounds show a high electron density at the C(2) position and at the nitrone oxygen atom O(1). 13C N.m.r. spectra for a number of isatogens are reported and analysed. There is no obvious relationship between the calculated total valence electron densities and chemical shift values in these compounds. A σp+ value of 0.343 has been calculated for the isatogen ring when attached to a phenyl ring. This value corresponds most closely to that for the phosphonate mono-anion. The structures, as well as chemical and biological activities of isatogens are discussed in the light of these results.

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Article information


J. Chem. Soc., Perkin Trans. 1, 1986, 1005-1010
Article type
Paper

Isatogens: crystal structure, electron density calculations, and 13C nuclear magnetic resonance spectra

D. B. Adams, M. Hooper, C. J. Swain, E. S. Raper and B. Stoddart, J. Chem. Soc., Perkin Trans. 1, 1986, 1005
DOI: 10.1039/P19860001005

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