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4-Phenyldiazenyl-substituted 3,6-di-tert-butylcatechol: synthesis and azo-hydrazone equilibrium

Konstantin Alekseevich Martyanov 1
Konstantin Alekseevich Martyanov
, 
Arina Andreevna Tsybushkina 1
Arina Andreevna Tsybushkina
, 
Anton Vladimirovich Cherkasov 1
Anton Vladimirovich Cherkasov
, 
Alexey A Belikov 1
Alexey A Belikov
, 
Viacheslav Aleksandrovich Kuropatov 1
Viacheslav Aleksandrovich Kuropatov
1 G.A. Razuvaev Institute of Organometallic Chemistry, Russian Academy of Sciences, Nizhnii Novgorod, Russian Federation
10.1016/j.mencom.2024.06.038
Published 2024-06-19
Communication , Volume 34, Issue 4, 584-586
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Martyanov K. A. et al. 4-Phenyldiazenyl-substituted 3,6-di-tert-butylcatechol: synthesis and azo-hydrazone equilibrium // Mendeleev Communications. 2024. Vol. 34. No. 4. pp. 584-586.
GOST all authors (up to 50) Copy
Martyanov K. A., Tsybushkina A. A., Cherkasov A. V., Belikov A. A., Kuropatov V. A. 4-Phenyldiazenyl-substituted 3,6-di-tert-butylcatechol: synthesis and azo-hydrazone equilibrium // Mendeleev Communications. 2024. Vol. 34. No. 4. pp. 584-586.
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TY - JOUR
DO - 10.1016/j.mencom.2024.06.038
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.06.038
TI - 4-Phenyldiazenyl-substituted 3,6-di-tert-butylcatechol: synthesis and azo-hydrazone equilibrium
T2 - Mendeleev Communications
AU - Martyanov, Konstantin Alekseevich
AU - Tsybushkina, Arina Andreevna
AU - Cherkasov, Anton Vladimirovich
AU - Belikov, Alexey A
AU - Kuropatov, Viacheslav Aleksandrovich
PY - 2024
DA - 2024/06/19
PB - Mendeleev Communications
SP - 584-586
IS - 4
VL - 34
ER -
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@article{2024_Martyanov,
author = {Konstantin Alekseevich Martyanov and Arina Andreevna Tsybushkina and Anton Vladimirovich Cherkasov and Alexey A Belikov and Viacheslav Aleksandrovich Kuropatov},
title = {4-Phenyldiazenyl-substituted 3,6-di-tert-butylcatechol: synthesis and azo-hydrazone equilibrium},
journal = {Mendeleev Communications},
year = {2024},
volume = {34},
publisher = {Mendeleev Communications},
month = {Jun},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.06.038},
number = {4},
pages = {584--586},
doi = {10.1016/j.mencom.2024.06.038}
}
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Martyanov, Konstantin Alekseevich, et al. “4-Phenyldiazenyl-substituted 3,6-di-tert-butylcatechol: synthesis and azo-hydrazone equilibrium.” Mendeleev Communications, vol. 34, no. 4, Jun. 2024, pp. 584-586. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.06.038.

Keywords

azo compounds
azo–hydrazone tautomerism.
benzoquinones
dioxolene ligands
hydrazones
p-iminoquinone
photoresponsive ligands

Abstract

Reaction of 3-hydroxy-2,5-di-tert-butyl-1,4-benzoquinone with phenylhydrazine hydrochloride mainly leads to the corresponding hydrazone at the position 1 existing in tautomeric equilibrium with 3,6-di-tert-butyl-4-(phenyl- diazenyl)catechol. Thermodynamic parameters of the tautomerization were evaluated by NMR spectroscopy. The hydrazone structure was confirmed by XRD study.

References

.
Photopharmacological compounds based on azobenzenes and azoheteroarenes: principles of molecular design, molecular modelling, and synthesis
Ryazantsev M.N., Strashkov D.M., Nikolaev D.M., Shtyrov A.A., Panov M.S.
Russian Chemical Reviews, 2021
.
Molecular switches as photocontrollable "smart" receptors.
Natali M., Giordani S.
Chemical Society Reviews, 2012
.
Azobenzene photoswitches for biomolecules
Beharry A.A., Woolley G.A.
Chemical Society Reviews, 2011
.
Magnetic Bistability of Molecules in Homogeneous Solution at Room Temperature
Venkataramani S., Jana U., Dommaschk M., Sönnichsen F.D., Tuczek F., Herges R.
Science, 2011
.
Light-Driven Coordination-Induced Spin-State Switching: Rational Design of Photodissociable Ligands
Thies S., Sell H., Bornholdt C., Schütt C., Köhler F., Tuczek F., Herges R.
Chemistry - A European Journal, 2012
.
Redox Isomerism in o-Semiquinonato Cobalt Complexes in the Crystalline Phase
Zolotukhin A.A., Bubnov M.P., Cherkasov V.K., Abakumov G.A.
Russian Journal of Coordination Chemistry/Koordinatsionnaya Khimiya, 2018
.
Design of photocontrolled biomolecules based on azobenzene derivatives
Zatsepin T.S., Abrosimova L.A., Monakhova M.V., Le Thi Hien, Pingoud A., Kubareva E.A., Oretskaya T.S.
Russian Chemical Reviews, 2013
.
Heteroaryl azo dyes as molecular photoswitches
Crespi S., Simeth N.A., König B.
Nature Reviews Chemistry, 2019
.
Spin crossover in iron(III) complexes
Harding D.J., Harding P., Phonsri W.
Coordination Chemistry Reviews, 2016
.
Visible‐Light‐Activated Molecular Switches
Bléger D., Hecht S.
Angewandte Chemie - International Edition, 2015
.
Facile Synthesis of Catechol Azo Dyes
Haghbeen K., Tan E.W.
Journal of Organic Chemistry, 1998
.
Guest‐Driven Light‐Induced Spin Change in an Azobenzene Loaded Metal–Organic Framework
Xie K., Ruan Z., Lyu B., Chen X., Zhang X., Huang G., Chen Y., Ni Z., Tong M.
Angewandte Chemie - International Edition, 2021
.
Alkylation of catechol with cyclohexene. Novel sterically hindered o-quinones and catechols
Kocherova T.N., Druzhkov N.O., Martyanov K.A., Shavyrin A.S., Arsenyev M.V., Kulikova T.I., Baranov E.V., Kuropatov V.A., Cherkasov V.K.
Russian Chemical Bulletin, 2020
.
Reaction of 3,6-di-tert-butyl-o-benzoquinone with acids
Novikova I.A., Vol'eva V.B., Komissarova N.L., Belostotskaya I.S., Ershov V.V.
Russian Chemical Bulletin, 1981
.
Spin transitions in ferric catecholate complexes mediated by outer-sphere counteranions
Chegerev M., Demidov O., Vasilyev P., Efimov N., Kubrin S., Starikov A., Vlasenko V., Piskunov A., Shapovalova S., Guda A., Rusalev Y., Soldatov A.
Dalton Transactions, 2022
.
The Structures of Arylhydrazones of Unsymmetrically Substituted Quinones
Smith L.I., Irwin W.B.
Journal of the American Chemical Society, 1941
.
Advances and opportunities in the exciting world of azobenzenes
Jerca F.A., Jerca V.V., Hoogenboom R.
Nature Reviews Chemistry, 2021
.
Switchable metallacycles and metallacages
Lin H., Wang Y., Shi X., Yang H., Xu L.
Chemical Society Reviews, 2023