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A 13C and 1H NMR study of the geometries of the 1,3-dicyanoallyl anion: Thermal and photochemical interconversion

✍ Scribed by D. R. Boate; D. H. Hunter

Publisher: John Wiley and Sons
Year: 1984
Tongue: English
Weight: 411 KB
Volume: 22
Category: Article
ISSN: 0749-1581
DOI: 10.1002/mrc.1270220307

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✦ Synopsis

Abstract

Glutacononitrile (1,3‐dicyanopropene) (2) was converted to its anion (1) by treatment with sodium hydride in tetrahydrofuran. Both ^13^C and ^1^ NMR showed that the sodium salt of 1 in THF existed in three slowly interconverting geometries (U, W and S). These geometries were present in similar amounts but the relative amounts of each proved to be concentration dependent. Irradiation of a 0.01 M solution of 1 at −80°C led to the conversion of a mixture of the U, W and S forms of 1 to only the W and S forms. Upon warming to 0°C equilibrium was re‐established with a half‐life of approximately 8 h.

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