DFT and FT-IR analyses of hydrogen bonding in 3-substistuted-3-oxo-arylhydrazonopropanenitriles

Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy
Ihsan M Kenawi, Mohamed H Elnagdi

Abstract

Ab initio calculations, FT-IR and X-ray crystal analysis, indicated that the most stable configuration of 3-oxo-2-(phenylhydrazono)-3-(thien-2-yl)-propionitrile is the anti phenylhydrazone structure 1. Stability of such a conformation, over the possible E-form, 2, that would be stabilized by intramolecular hydrogen bonding, is due to interaction between electron-pair domains of the N, S and O atoms. However, the simulated and experimental IR frequency data indicated intermolecular hydrogen bonding between NH and CN, the latter being lowered to 2214 cm(-1). Studies on 3-oxo-3-phenyl-2-(phenylhydrazono)-propionitrile showed the same result, as well as, another intramolecular hydrogen association of the type N-H...O. This was clearly indicated by the absorbance of the carbonyl stretch at 1605 cm(-1). These data indicated the existence of a bifurcated hydrogen bond in 1a and a single intermolecular association in 1b.

References

Sep 15, 1988·Physical Review A: General Physics·A D Becke
Feb 1, 2003·Clinical Chemistry·Frédéric CottonJean-Marie Boeynaems

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