Effect of the Nature of Nitrogen-Containing Organic Base on Destruction of Octa(4-tert-butylphenyl)tetrapyrazinoporphyrazine

Cover Page

Cite item

Full Text

Open Access Open Access
Restricted Access Access granted
Restricted Access Subscription Access

Abstract

The properties of octa(4-tert-butylphenyl)tetrapyrazinoporphyrazine in 2-methylpyridine were studied. During the acid-base interaction of molecules, a kinetically stable complex was formed with proton transfer. The addition of morpholine, piperidine, n-butylamine, and diethylamine to 2-methylpyridine led to the destruction of this complex, unlike the addition of tert-butylamine and triethylamine. The influence of the proton-accepting ability and spatial structure of the nitrogen-containing base, as well as the basicity of the medium, on the process of the tetrapyrazinoporphyrazine macrocycle decomposition was considered, and a destruction scheme was proposed.

Full Text

Restricted Access

About the authors

O. A. Petrov

Ivanovo State University of Chemistry and Technology

Author for correspondence.
Email: poa@isuct.ru
ORCID iD: 0000-0003-3424-7135
Russian Federation, Ivanovo, 153000

K. A. Volzhankina

Ivanovo State University of Chemistry and Technology

Email: poa@isuct.ru
ORCID iD: 0009-0009-9355-3600
Russian Federation, Ivanovo, 153000

References

  1. Novakova V., Donzello M.P., Ercolani C., Zimcik P., Stuzhin P. // Coord. Chem. Rev. 2018. Vol. 361. Р. 1. doi: 10.1016/j.ccr.2018.01.015
  2. Петров О.А. // Изв. АН. Сер. хим. 2022. Т. 71. С. 613; Petrov O.A. // Russ. Chem. Bull. 2022. Vol. 71. P. 613. doi: 10.1007/S11172-022-34-59-5
  3. Петров О.А.// ЖФХ. 2022. Т. 96. № 3. С. 324; Petrov O.A. // Russ. J. Phys. Chem. (A). 2022. Vol. 96. N 3. P. 470. doi: 10.31857/S0044453722030207
  4. Петров О.А. // ЖОрХ. 2022. Т. 58. № 3. С. 303; Petrov O.A. // Russ. J. Org. Chem. 2022. Vol. 58. N 3. P. 315. doi: 10.31857/S05147492220300
  5. Donzello M.P., Ou Z., Monacelli F., Ricciardi G., Rizzoli C., Ercolani C., Kadish K.M. // Inorg. Chem. 2004. Vol. 43. N 7. P. 8626. doi: 10.1021/ic048909w
  6. Молекулярные взаимодействия / Под ред. Г. Ратайчак, У. Орвилл-Томаса. М.: Мир, 1984. 599 с.
  7. Zundell G. Hydrogen Bonds with Large Proton Polarizability and Transfer Processes in Electrochemistry and Biology / Eds I. Prigogin, S.F. Rise. New York: Willy and Sons Inc., 2000. 217 p.
  8. Райхардт К. Растворители и эффекты среды в органической химии. М.: Мир, 1991.764 с.
  9. The Hadbook of Chemistry and Physics / Ed. W.M. Haynes. Boca Raton; London; New York: Taylor and Francis, 2013. 2668 p.
  10. Stuzhin P.A. // J. Porph. Phthal. 2003. Vol. 7. P. 813. doi: 10.1142/s1088424603001014
  11. Фиалков Ю.Я. // Растворители как средство управления химическим процессом. Л.: Химия, 1990. 237 с.
  12. Blackburne I.D., Katritzky A.R., Takeuchi Y. // Acc. Chem. Res. 1975. Vol. 8. P. 300. doi: 10.1021/ar50093a003
  13. Anet F.A.L., Yavari I. // J. Am. Chem. Soc. 1977. Vol. 99. P. 2794. doi: 10.1021/ja00450a064
  14. Иванова Ю.Б., Дмитриева О.А., Хрушкова Ю.В., Любимова Т.В., Семейкин А.С., Мамардашвили Н.Ж. // ЖОХ. 2020. Т. 90. № 4. С. 760; Ivanova Yu.B., Dmitrieva O.A., Khrushkova Yu.B., Lyubimova T.V., Semeikin A.S., Mamardashvili N.Z. // Russ. J. Gen. Chem. 2020. Vol. 90. N 4. P. 817. doi: 10.31857//S0044460Х20050157

Supplementary files

Supplementary Files
Action
1. JATS XML
Download
2. Scheme 1.

Download (68KB)
Indexing metadata
3. Fig. 1. The electronic absorption spectrum of H2PA(Pyz)4R8 in benzene at 298 K.

Download (54KB)
Indexing metadata
4. Fig. 2. The electronic absorption spectrum of H2PA(Pyz)4R8 in 2-methylpyridine at 298 K.

Download (50KB)
Indexing metadata
5. Fig. 3. Change in the electronic absorption spectrum H2PA(Pyz)4R8*2MePy in the 2-methylpyridine–di- ethylamine system for 65 min at [Et2NH] = 2.41 mol/l at 323 K.

Download (76KB)
Indexing metadata
6. Fig. 4. Change in the electronic absorption spectrum H2PA(Pyz)4R8*2MePy in the 2-methylpyridine–morpholine system for 47 min at cMorph = 2.87 mol/l at 318 K.

Download (72KB)
Indexing metadata
7. Fig. 5. Dependence of lg(c0/c) on the destruction time of the H2PA(Pyz)4R8×2MePy complex in BuNH2(1), Et2NH (2), Morph (3), Pip (4) at T = 298 (3, 4), 318 (1), 323 K (2) and [BuNH2] = 2.53, [Et2NH] = 7.25, [Morph] = 8.61, [Pip] = 2.53 mol/l.

Download (63KB)
Indexing metadata
8. Fig. 6. Dependence of lgkn on lgc0 B Destruction reactions H2PA(Pyz)4R8*2MePy in the presence of BuNH2(1), Et2NH (2), Morph (3), Pip (4) in 2-methylpyridine at T = 298 (1), 303 (2), 308 (3) and 318 K (4).

Download (60KB)
Indexing metadata

Copyright (c) 2024 Russian Academy of Sciences