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Solid state tautomerism in 2-((phenylimino)methyl)naphthalene-1-ol

Nedeltcheva, Daniela ; Kamounah, Fadhil S. ; Mirolo, Laurent ; Fromm, Katharina M. ; Antonov, Liudmil

In: Dyes and Pigments, 2009, vol. 83, no. 1, p. 121-126

The solid state tautomerism of 2-((phenylimino)methyl)naphthalene-1-ol was studied using X-ray measurements and absorption spectroscopy. In the solid state, the keto tautomer predominates. The observed shift in the equilibrium from the enol (dilute solution) to the keto (solid state) forms is explained by the formation of dye aggregates using ab initio quantum chemical calculations.