Journal
RUSSIAN CHEMICAL BULLETIN
Volume 57, Issue 9, Pages 1989-1995Publisher
SPRINGER
DOI: 10.1007/s11172-008-0267-5
Keywords
hydroxyformylcoumarins; imines; solvatochromism; E/Z-isomerization
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Funding
- Russian Foundation for Basic Research [08-03-90016_Bel_a]
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Aromatic imines, namely, 5-formyl-6-hydroxy-4-methyl- and 8-formyl-7-hydroxy-4-methylcoumarin derivatives, have been synthesized. A dependence of their spectral characteristics ((1)H NMR spectra, electronic absorption spectra) from the solvent (DMSO, CHCl(3), DMF, acetonitrile, MeOH) has been studied. The solvatochromic effects observed for a number of imines, first of all, for 7-hydroxy-4-methyl-8-(4'-nitrophenylimino)methyl-2H-1-benzopyran-2-one, were related to their E/Z-isomerization with respect to the C=N bond based on the quantum chemical calculations by the AM1, PM3, PPP CI methods.
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