Tetrahedron, volume 93, pages 132312

Selective colorimetric sensor for cyanide anion based on 1-hydroxyanthraquinone

Kudrevatykh Alexandra A 2
Ushakov Evgeny N
Korchagin Denis V
Sulimenkov Ilia V
Vasilev Sergey G
Ushakov E.N. 1
Sulimenkov Ilia V 3
Publication typeJournal Article
Publication date2021-07-01
Journal: Tetrahedron
Quartile SCImago
Q2
Quartile WOS
Q3
Impact factor2.1
ISSN00404020, 14645416
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
Abstract The article addresses the synthesis, structure and properties of 2-benzoylamino-1-hydroxyanthraquinone (1a), which can function as a selective colorimetric sensor for the cyanide anion in aqueous media. Compound 1a was prepared in two simple steps in good yield and its structure was confirmed by X-ray diffraction analysis. UV–Vis and NMR spectroscopy, mass spectrometry and quantum chemistry studies revealed that in MeCN–H2O mixtures (95:5, v/v), cyanide ionizes the hydroxyl group of the anthraquinone, which results in a strong bathochromic effect. The association constant of cyanide anion with 1a was measured to be 104.88 M–1; the detection limit is about 0.22 μM. The presence of a benzoylamino group at position 2 of the anthraquinone core has a stabilizing effect on the anionic form of 1a due to the hydrogen bonding between the amide hydrogen atom and the oxygen atom of the ionized hydroxyl group.

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Martyanov T. P. et al. Selective colorimetric sensor for cyanide anion based on 1-hydroxyanthraquinone // Tetrahedron. 2021. Vol. 93. p. 132312.
GOST all authors (up to 50) Copy
Martyanov T. P., Kudrevatykh A. A., Ushakov E. N., Korchagin D. V., Sulimenkov I. V., Klimenko L. S., Vasilev S. G., Gromov S. P., Ushakov E., Korchagin D., Sulimenkov I. V., Vasil’ev S. K., Fomina M. V. Selective colorimetric sensor for cyanide anion based on 1-hydroxyanthraquinone // Tetrahedron. 2021. Vol. 93. p. 132312.
RIS |
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RIS Copy
TY - JOUR
DO - 10.1016/J.TET.2021.132312
UR - https://doi.org/10.1016%2FJ.TET.2021.132312
TI - Selective colorimetric sensor for cyanide anion based on 1-hydroxyanthraquinone
T2 - Tetrahedron
AU - Martyanov, Timofey P
AU - Kudrevatykh, Alexandra A
AU - Ushakov, Evgeny N
AU - Korchagin, Denis V
AU - Sulimenkov, Ilia V
AU - Klimenko, Lyubov S
AU - Vasilev, Sergey G
AU - Gromov, Sergey P
AU - Ushakov, E.N.
AU - Korchagin, Denis
AU - Sulimenkov, Ilia V
AU - Vasil’ev, S. K.
AU - Fomina, Marina V.
PY - 2021
DA - 2021/07/01 00:00:00
PB - Elsevier
SP - 132312
VL - 93
SN - 0040-4020
SN - 1464-5416
ER -
BibTex
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BibTex Copy
@article{2021_Martyanov
author = {Timofey P Martyanov and Alexandra A Kudrevatykh and Evgeny N Ushakov and Denis V Korchagin and Ilia V Sulimenkov and Lyubov S Klimenko and Sergey G Vasilev and Sergey P Gromov and E.N. Ushakov and Denis Korchagin and Ilia V Sulimenkov and S. K. Vasil’ev and Marina V. Fomina},
title = {Selective colorimetric sensor for cyanide anion based on 1-hydroxyanthraquinone},
journal = {Tetrahedron},
year = {2021},
volume = {93},
publisher = {Elsevier},
month = {jul},
url = {https://doi.org/10.1016%2FJ.TET.2021.132312},
pages = {132312},
doi = {10.1016/J.TET.2021.132312}
}
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