Protonation of ninhydrin and indan-1,2,3-trione revisited: A combined theoretical and experimental study Full article
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Journal of Molecular Structure
ISSN: 0022-2860 , E-ISSN: 1872-8014 |
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| Output data | Year: 2017, Volume: 1134, Pages: 1-5 Pages count : 5 DOI: 10.1016/j.molstruc.2016.12.057 | ||||
| Tags | Ninhydrin; Superacid; NMR; Quantum chemistry calculations | ||||
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Abstract:
The literature data on protonation of indan-1,2,3-trione and ninhydrin (indantrione hydrate) in acidic media are inconsistent, formation of dications at pH 3 and very low extent of protonation in superacid CF3SO3H were claimed. Our combined theoretical (DFT, MP2, CCSD) and experimental (NMR) study has shown that indantrione undergoes single protonation in CF3SO3H resulting in monocation formation. In more strong superacid FSO3H-SbF5 dication is formed, but, contrary to the literary data, trication is not formed even in this superacid. Significant dependence of C-13 NMR chemical shifts of indantrione on media acidity allows using this compound as a convenient indicator of acidity in a broad range, from Ho -3 to -25. (C) 2016 Elsevier B.V. All rights reserved.
Cite:
Salnikov G.E.
, Genaev A.M.
, Shernyukov A.V.
, Shubin V.G.
Protonation of ninhydrin and indan-1,2,3-trione revisited: A combined theoretical and experimental study
Journal of Molecular Structure. 2017. V.1134. P.1-5. DOI: 10.1016/j.molstruc.2016.12.057 WOS Scopus РИНЦ OpenAlex
Protonation of ninhydrin and indan-1,2,3-trione revisited: A combined theoretical and experimental study
Journal of Molecular Structure. 2017. V.1134. P.1-5. DOI: 10.1016/j.molstruc.2016.12.057 WOS Scopus РИНЦ OpenAlex
Dates:
| Published print: | Apr 1, 2017 |
Identifiers:
| Web of science: | WOS:000394919100001 |
| Scopus: | 2-s2.0-85007328532 |
| Elibrary: | 29469510 |
| OpenAlex: | W2566205250 |