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BENZENOID-QUINOID TAUTOMERISM OF AZOMETHINES AND THEIR STRUCTURAL ANALOGS BENZENOID-QUINOID TAUTOMERISM OF 4-HYDROXY-5,6-BENZOCINNAMALDEHYDE IMINES
Andreeva, I. M.,Babeshko, O. M.,Bondarenko, E. M.,Medyantseva, E. A.,Minkin, V. I.
, p. 1864 - 1869 (2007/10/02)
In the crystalline state and in solutions in nonpolar solvents 4-hydroxy-5,6-benzocinnamaldehyde has a benzenoid structure.In ethanol and DMSO tautomerism between the hydroxyaldehyde and p-hydroxymethylenequinone forms is observed.The N-aryl- and N-alkylimines of 4-hydroxy-5,6-benzocinnamaldehyde have the quinonoid structure in the crystalline state.In nonpolar solvents the n-arylimines axist in the form of the benzenoid tautomers, while a benzenoid-quinonoid equilibrium is observed for the N-alkylimines.In polar solvents the N-arylimines exhibit a tendency for quinonoidization.In these solvents the N-alkylimines exist preferentially in the form of the quinonoid structures.
