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Molecules 2017, 22(11), 1961; doi:10.3390/molecules22111961

Effect of Structure on Charge Distribution in the Isatin Anions in Aprotic Environment: Spectral Study

1
Faculty of Natural Sciences, Institute of Chemistry, Comenius University, Ilkovičova 6, Mlynská dolina CH-2, SK-842 15 Bratislava, Slovakia
2
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Comenius University, Odbojárov 10, SK-832 32 Bratislava, Slovakia
*
Author to whom correspondence should be addressed.
Received: 18 October 2017 / Revised: 13 November 2017 / Accepted: 9 November 2017 / Published: 14 November 2017
(This article belongs to the Section Physical Chemistry)
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Abstract

Five isatin anions were prepared by deprotonation of initial isatins in aprotic solvents using basic fluoride and acetate anions (F and CH3COO). The F basicity is sufficient to deprotonate isatin NH hydrogen from all the studied compounds. This process is reversible. In the presence of proton donor solvents, the anions form the corresponding isatins. The isatin hydrogen acidity depends on the overall structure of the isatin derivatives. The anions were characterized by ultraviolet–visible (UV–Vis), Fourier transform infrared (FTIR) and nuclear magnetic resonance (NMR) spectroscopy. Interestingly, the anions form aggregates at concentrations above 10−3 mol·dm−3. Further, the effect of cations on the UV–Vis spectra of the studied anions was studied. Charge transfer and its distribution in the anion depends on the radius and the cation electron configuration. The alkali metal cations, tetrabutylammonium (TBA+), Mg2+ and Ag+, interact with the C-2 carbonyl oxygen of the isatin anion. The interaction has a coulombic character. On the other hand, Cd2+, Zn2+, Hg2+, Co2+, and Cu+ cations form a coordinate bond with the isatin nitrogen. View Full-Text
Keywords: isatin azanions; azanion aggregation; counterion effect; UV–Vis; FTIR; NMR spectroscopy isatin azanions; azanion aggregation; counterion effect; UV–Vis; FTIR; NMR spectroscopy
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Tisovský, P.; Šandrik, R.; Horváth, M.; Donovalová, J.; Jakusová, K.; Cigáň, M.; Sokolík, R.; Gáplovský, A.; Gáplovský, M.; Filo, J. Effect of Structure on Charge Distribution in the Isatin Anions in Aprotic Environment: Spectral Study. Molecules 2017, 22, 1961.

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