Abstract

The configuration of two oxime groups in cis-2-butenedialdioxime, unsymmetrical compound conjugated by three double bonds, is determined by a NMR study on the effects of the solvent, temperature and concentration; it is certain that, in solutions of usual conditions, the configuration exists as only "syn-syn". And the relative strengths of the hydrogen bond between these oxime groups and several solvents are compared and somc effects of the temperature and concentration are also considered. The several models of hydrogen bond between oxime and solvents are proposed; especially it is to be noted here that the hydrogen bond in pyridine solvent is not resulted from the interaction between a lone electron pair on nitrogen atom of pyridine and the hydroxyl proton of oxime, but the result of $\pi$-complex formed between the $\pi$-orbital of pyridine and the hydroxyl proton of the solute.

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1. Tetrahedron v.24 G.J. Karabatsos;R.A. Taller
2. J. Amer. Chem. Soc. v.85 G.J. Karabatsos;R. A. Taller;F.M. Vane
3. J. Amer. Chem. Soc. v.85 G.J. Karabatsos;R. A. Taller;F.M. Vane
4. Tetrahedron v.24 G.J. Karabatsos;C.E. Osborne
5. J. Amer. Chem. Soc. v.85 G.J. Karabatsos;R.A. Taller
6. J. Amer. Chem. Soc. v.86 G.J. Karabatsos;F.M. Vane;R.A. Taller;N. Hsi
7. Tetrahedron v.23 G.J. Karabatsos;N. Hsi
8. Tetrahedron v.24 G.J. Karabatsos;R.A. Taller
9. Tetrahedron v.24 G.J. Karabatsos;S.S. Lande
10. J. Chem. Phys. v.37 J.A. Pople
11. Applications of Neuclear Magnetic Resonance Spectroscopy in Organic Chemistry L.M. Jackman;S. Sternhell
12. Tetrahedron Letters v.18 G.J. Karabatsos;R.A. Taller;F.M. Vane
13. J. Korean Chem. Soc. v.19 Young-Suek Hong;Hak-Ki Lee;Byung-Kack Pack
14. Tetrahedron v.24 G.J. Karabatsos;R.A. Taller
15. J. Org. Chem. v.36 J.V. Burakevich;A.M. Lore;G.P. Volpp
16. Tetrahedron v.23 G.J. Karabatsos;K.L. Krumel