Protonation of ninhydrin and indan-1,2,3-trione revisited: A combined theoretical and experimental study

Protonation of ninhydrin and indan-1,2,3-trione revisited: A combined theoretical and experimental study Full article

Journal

Journal of Molecular Structure
ISSN: 0022-2860 , E-ISSN: 1872-8014

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

Authors

Salnikov George E. ^1,2 , Genaev Alexander M. ¹ , Shernyukov Andrey V. ¹ , Shubin Vyacheslav G. ¹

Affiliations

1	(Данные Web of science) Vorozhtsov Novosibirsk Inst Organ Chem, Acadamician Lavrentev Ave 9, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Univ, Pirogova St 2, Novosibirsk 630090, Russia

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.

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

Published print:

Apr 1, 2017

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