US EPA

1189795 

Journal Article 

Solvatochromism in N-(2-hydroxybenzylidene)aniline, N-(2-hydroxybenzylidene)benzylamine, and N-(2-hydroxybenzylidene)-2-phenylethylamine 

Gegiou, D; Lambi, E; Hadjoudis, E 

1996 

1 

Journal of Physical Chemistry
ISSN: 0022-3654 

100 

45 

17762-17765 

10.1021/jp961115l 

WOS:A1996VR57000011 

http://://WOS:A1996VR57000011
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Solvatochromism is found stronger in N-(2-hydroxybenzylidene)benzylamine (II) and N-(2-hydroxybenzylidene)-2-phenylethylamine (III) than in N-(2-hydroxybenzylidene)aniline (I) because of the increased basicity of the imine nitrogen in the ground state. Electronic absorption and FT-IR spectroscopic studies have provided evidence for an enol-keto tautomerism in all three compounds investigated in methanol, while both keto and protonated tautomers have been observed in their solutions in 2,2,2-trifluoroethanol and in 1,1,1,3,3,3-hexafluoro-2-propanol. The increase of the C=N stretching frequency upon protonation is found to be 21-18 cm-1 in the compounds investigated in acidic solvents. The higher frequency of the quadrant doublet in the FT-IR spectrum of I is associated with the aromatic stretching vibrations of the aniline ring. © 1996 American Chemical Society.