Unrevealing mechanism of the thermal tautomerization of avobenzone by means of quantum chemical computations

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Marko Kojić
Milena Petković
Mihajlo Etinski

Abstract

Avobenzone (1-(4-tert-butylphenyl)-3-(4-methoxyphenyl)propane-
-1,3-dione) is one of the most widely used UVA filters in cosmetic sunscreens. The reactivity of avo­benzone is complex and challenging to understand, due to a presence of tran­sient tautomers. In this contribution, the chelated enol, rotamer and keto tauto­mers of a reduced model of avobenzone, which are involved in keto–enol tau­to­merization, were studied. Two thermal tautomerization mechanisms are postulated and their transient structures are discussed. The computed vertical and adiabatic electronic excitation energies of the tautomers provide an addi­tional insight into the excited state properties of the tautomers.

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How to Cite
[1]
M. Kojić, M. Petković, and M. Etinski, “Unrevealing mechanism of the thermal tautomerization of avobenzone by means of quantum chemical computations”, J. Serb. Chem. Soc., vol. 81, no. 12, pp. 1393–1406, Dec. 2016.
Section
Theoretical Chemistry

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