Predicting the Keto-Enol Equilibrium from Combining UV/Visible Absorption Spectroscopy with Quantum Chemical Calculations of Vibronic Structures for Many Excited States-A Case Study on Salicylideneanilines

Zutterman Freddy;LOUANT, Orian;Mercier, Gabriel;Leyssens, Tom;Champagne, Benoit
(2018) The Journal of Physical Chemistry Part A : Molecules,Spectroscopy,Kinetics,Environment and General Theory — (2018)

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Authors
  • Zutterman Freddyautre
    Author
  • LOUANT, OrianUNamur
    Author
  • Mercier, GabrielUCLouvain
    Author
  • Leyssens, TomUCLouvain
    Author
  • Champagne, BenoitUNamur
    Author
Abstract
Salicylideneanilines are characterized by a tautomer equilibrium, between an enol and a keto form of different colors, at the origin of their remarkable thermochromic, solvatochromic, and photochromic properties. The enol form is usually the most stable but appropriate choice of substituents and conditions (solvent, crystal, host compound) can displace the equilibrium towards the keto form so that there is a need for fast prediction of the keto: enol abundance ratio. Here we demonstrate the reliability of a combined theoretical-experimental method, based on comparing simulated and measured UV/visible absorption spectra. The calculations of the excitation energies, oscillator strengths, and vibronic structures of both enol and keto forms are performed at the time-dependent density functional theory level of calculations by accounting for solvent effects using the polarizable continuum model.
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Zutterman Freddy, LOUANT, O., Mercier, G., Leyssens, T., & Champagne, B. (2018). Predicting the Keto-Enol Equilibrium from Combining UV/Visible Absorption Spectroscopy with Quantum Chemical Calculations of Vibronic Structures for Many Excited States-A Case Study on Salicylideneanilines. The Journal of Physical Chemistry Part A : Molecules,Spectroscopy,Kinetics,Environment and General Theory. Published. https://hdl.handle.net/2078.5/47404 (Original work published 2018)