Abstract
A study is performed of patterns of the destruction of β-substituted and β,β-annelated porphyrazines in the presence of cyclic and acyclic nitrogen-containing bases in dimethylsulfoxide. Possible schemes of the mechanism are proposed and substantiated. It is shown how the NH acidity of the porphyrazine macrocycle, the spatial structure of the nitrogen-containing base, and its proton-acceptor ability affect the kinetic parameters of destruction. Structural data of proton-transfer complexes in dimethylsulfoxide are discussed.
Similar content being viewed by others
REFERENCES
V. Novakova, M. P. Donzello, C. Ercolani, et al., Coord. Chem. Rev. 361 (4), 1 (2018).
J. L. Sessler, Ph. Gale, and W.-S. Cho, Anion Receptor Chemistry (Roy. Soc. Chem., London, 2006).
P. A. Stuzhin, J. Porphyr. Phthalocyan. 3, 500 (1999).
P. A. Stuzhin, J. Porphyr. Phthalocyan. 7, 813 (2003).
O. A. Petrov, Russ. J. Phys. Chem. A 95, 696 (2021).
O. A. Petrov, Russ. J. Phys. Chem. A 74, S454 (2000).
O. A. Petrov, G. V. Osipova, and E. L. Kuzmina, Russ. J. Gen. Chem. 81, 1211 (2011).
O. A. Petrov, G. V. Osipova, V. E. Maizlish, and A. V. Rodionov, Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol. 57 (6), 54 (2014).
G. V. Osipova, O. A. Petrov, and S. V. Efimova, Russ. J. Gen. Chem. 83, 562 (2013).
O. A. Petrov, A. P. Stuzhin, and Yu. B. Ivanova, Russ. J. Phys. Chem. A 82, 201 (2008).
O. A. Petrov, A. N. Kiselev, and S. A. Syrbu, Russ. J. Gen. Chem. 84, 1732 (2014).
O. A. Petrov, A. N. Kiselev, and S. A. Syrbu, Ross. Khim. Zh. 60 (2), 89 (2016).
O. A. Petrov, A. N. Kiselev, Z. A. Teletskii, and A. O. Belyaeva, Russ. J. Gen. Chem. 89, 429 (2019).
O. A. Petrov, K. A. Aganicheva, G. A. Gamov, and A. N. Kiselev, Russ. J. Phys. Chem. A 94, 1843 (2020).
E. L. Kuzmina and O. A. Petrov, Zh. Obshch. Khim. 82, 850 (2012).
O. A. Petrov, O. G. Khelevina, and N. V. Chizhova, Russ. J. Coord. Chem. 23, 130 (1997).
E. A. Kokareva, O. A. Petrov, and O. G. Khelevina, Macroheterocycles 2, 157 (2009).
Molecular Interactions, Ed. by H. Ratajczak and W. J. Orwill-Thomas (Wiley, New York, 1989).
G. Zundell, Hydrogen Bonds with Large Proton Polarizability and Transfer Processes in Electrochemistry and Biology, Ed. by I. Prigogine and S. F. Rise (Wiley, New York, 2000).
C. Reichardt, Solvents and Solvent Effects in Organic Chemistry (VCH, Weinheim, 1988).
P. Stuzhin, O. Khelevina, and B. Berezin, Phthalocyanines: Properties and Applications (VCH, New York, 1996), Vol. 4, p. 23.
O. A. Petrov, E. L. Kuzmina, V. E. Maizlish, and A. V. Rodionov, Russ. J. Phys. Chem. A 88, 7 (2014).
The Handbook of Chemistry and Physics, Ed. by W. M. Haynes (Taylor and Francis, Boca Raton, 2013).
F. A. L. Anet and I. Yavari, J. Am. Chem. Soc. 99, 2794 (1977).
I. D. Blackburne, A. R. Katritzky, and Y. Takeuchi, Acc. Chem. Res. 8, 300 (1975).
Funding
This work was supported by the Ivanovo State University of Chemistry and Technology, grant no. 13-ISUCT-21.
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
The authors declare they have no conflicts of interest.
Additional information
Translated by K. Utegenov
Rights and permissions
About this article
Cite this article
Petrov, O.A. Destruction of Porphyrazines in Organic Proton-Acceptor Media. Russ. J. Phys. Chem. 96, 470–477 (2022). https://doi.org/10.1134/S0036024422030207
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S0036024422030207