IR spectral and structural changes caused by the conversion of 3-methoxy-4-hydroxybenzaldehyde (vanillin) into the oxyanion

Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy
E A Velcheva, B A Stamboliyska

Abstract

The spectral and structural changes, caused by the conversion of the vanillin molecule into the corresponding oxyanion have been studied by IR spectra and normal coordinate calculations within the Onsager self-consistent reaction field (SCRF) model, using a density functional theory (DFT) method at the Becke3LYP/6-31+G** level. Structures of all conformational isomers of vanillin and of its anion have been located, as well as their total and relative energies have been determined. The conversion leads to geometry changes in the whole species, due to the strong O-/acceptor polar resonance through the para phenylene ring. The conversion causes a 41 cm(-1) decrease in the frequency of the carbonyl stretching band nu(C=O), strong intensity increases (1.6 - 7.2-fold) of the aromatic skeletal nu8 and nu19 as well as formyl nu(CH) bands. According to the calculations the oxyanionic charge is delocalized over aldehyde group (0.25 e-), phenylene ring (0.13 e-), methoxy group (0.07 e-) and oxyanyonic center (0.55 e-).

References

Aug 10, 1996·Lancet·J A Haines
Apr 26, 2003·Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy·B A StamboliyskaI G Binev

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Citations

Aug 6, 2004·Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy·Yuri I BinevLalka I Daskalova
Nov 5, 2008·Chemical & Pharmaceutical Bulletin·Seikou NakamuraMasayuki Yoshikawa
Aug 20, 2010·Physical Chemistry Chemical Physics : PCCP·Emilio J CocineroFernando Castaño

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