The nature of bathochromic shift in the solvated chloranilic acid: A quantum chemical approach

The limitations of author's modification of the well-known method for determination of water content in organic solvents with chloranilic acid (CAA) [Anal. Chim. Acta 16 (1962) 494] are illustrated. An insight into the CAA solvatochromism at the molecular level is proposed on the basis of quant...

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Bibliographic Details
Published in:Journal of molecular liquids 2015-11, Vol.211, p.187-191
Main Authors: Blank, T.A., Ostras', K.S., Shishkin, O.V., Zhikol, O.A., Palamarchuk, G.V., Eksperiandova, L.P.
Format: Article
Language:English
Subjects:
Charge–transfer complex
Chloranilic acid
Electronic spectra
Solvatochromism
Time-dependent DFT
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Summary:The limitations of author's modification of the well-known method for determination of water content in organic solvents with chloranilic acid (CAA) [Anal. Chim. Acta 16 (1962) 494] are illustrated. An insight into the CAA solvatochromism at the molecular level is proposed on the basis of quantum-chemical calculations. The bathochromic shift is explained by CAA anion formation in an interaction with the solvent. Deprotonation of CAA depends substantially on the solvent, both on the first solvation shell microstructure and on the bulk solvent phase. The deprotonation equilibrium, responsible for the long-wavelength absorption, limits applicability of the analytical method. [Display omitted] •The bathochromic shift of chloranilic acid absorption is due to it monoanion.•Protic solvents are required to form a strong hydrogen bond with the anion.•The deprotonation equilibrium limits the applicability of the analytical method.
ISSN:0167-7322
1873-3166
DOI:10.1016/j.molliq.2015.07.015