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Protonation of ninhydrin and indan-1,2,3-trione revisited : A combined theoretical and experimental study. / Salnikov, George E.; Genaev, Alexander M.; Shernyukov, Andrey V. et al.

In: Journal of Molecular Structure, Vol. 1134, 15.04.2017, p. 1-5.

Research output: Contribution to journal › Article › peer-review

Harvard

Salnikov, GE, Genaev, AM, Shernyukov, AV & Shubin, VG 2017, 'Protonation of ninhydrin and indan-1,2,3-trione revisited: A combined theoretical and experimental study', Journal of Molecular Structure, vol. 1134, pp. 1-5. https://doi.org/10.1016/j.molstruc.2016.12.057

APA

Salnikov, G. E., Genaev, A. M., Shernyukov, A. V., & Shubin, V. G. (2017). Protonation of ninhydrin and indan-1,2,3-trione revisited: A combined theoretical and experimental study. Journal of Molecular Structure, 1134, 1-5. https://doi.org/10.1016/j.molstruc.2016.12.057

Vancouver

Salnikov GE, Genaev AM, Shernyukov AV, Shubin VG. Protonation of ninhydrin and indan-1,2,3-trione revisited: A combined theoretical and experimental study. Journal of Molecular Structure. 2017 Apr 15;1134:1-5. doi: 10.1016/j.molstruc.2016.12.057

Author

Salnikov, George E. ; Genaev, Alexander M. ; Shernyukov, Andrey V. et al. / Protonation of ninhydrin and indan-1,2,3-trione revisited : A combined theoretical and experimental study. In: Journal of Molecular Structure. 2017 ; Vol. 1134. pp. 1-5.

BibTeX

@article{7f5db5ebc8e84e1db235d853479ba96f,
title = "Protonation of ninhydrin and indan-1,2,3-trione revisited: A combined theoretical and experimental study",
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 13C NMR chemical shifts of indantrione on media acidity allows using this compound as a convenient indicator of acidity in a broad range, from H0 −3 to −25.",
keywords = "Ninhydrin, NMR, Quantum chemistry calculations, Superacid, AROMATIC-COMPOUNDS",
author = "Salnikov, {George E.} and Genaev, {Alexander M.} and Shernyukov, {Andrey V.} and Shubin, {Vyacheslav G.}",
year = "2017",
month = apr,
day = "15",
doi = "10.1016/j.molstruc.2016.12.057",
language = "English",
volume = "1134",
pages = "1--5",
journal = "Journal of Molecular Structure",
issn = "0022-2860",
publisher = "Elsevier",

}

RIS

TY - JOUR

T1 - Protonation of ninhydrin and indan-1,2,3-trione revisited

T2 - A combined theoretical and experimental study

AU - Salnikov, George E.

AU - Genaev, Alexander M.

AU - Shernyukov, Andrey V.

AU - Shubin, Vyacheslav G.

PY - 2017/4/15

Y1 - 2017/4/15

N2 - 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 13C NMR chemical shifts of indantrione on media acidity allows using this compound as a convenient indicator of acidity in a broad range, from H0 −3 to −25.

AB - 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 13C NMR chemical shifts of indantrione on media acidity allows using this compound as a convenient indicator of acidity in a broad range, from H0 −3 to −25.

KW - Ninhydrin

KW - NMR

KW - Quantum chemistry calculations

KW - Superacid

KW - AROMATIC-COMPOUNDS

UR - http://www.scopus.com/inward/record.url?scp=85007328532&partnerID=8YFLogxK

U2 - 10.1016/j.molstruc.2016.12.057

DO - 10.1016/j.molstruc.2016.12.057

M3 - Article

AN - SCOPUS:85007328532

VL - 1134

SP - 1

EP - 5

JO - Journal of Molecular Structure

JF - Journal of Molecular Structure

SN - 0022-2860

ER -

ID: 10040811