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 Научная публикация

Журнал

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

Вых. Данные

Год: 2017, Том: 1134, Страницы: 1-5 Страниц : 5 DOI: 10.1016/j.molstruc.2016.12.057

Ключевые слова

Ninhydrin; Superacid; NMR; Quantum chemistry calculations

Авторы

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

Организации

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

Опубликована в печати:

1 апр. 2017 г.

Web of science	WOS:000394919100001
Scopus	2-s2.0-85007328532
РИНЦ	29469510
OpenAlex	W2566205250