Статья
2020
Interaction between meso-Phenyl-Substituted Porphirinioids and Carboxylic Acids, and a Thermal Analysis of Their Cationic Salts
A. E. Likhonina, M. A. Krest’yaninov, F. K. Morshnev, E. L. Kritskii, T. V. Kudayarova, D. B. Berezin
Российский журнал физической химии А
https://doi.org/10.1134/S0036024420010185
Abstract / Full Text
Thermogravimetry and quantum chemistry, including NBO analysis, are used to study the thermal stability and NH acidity of single and double protonated forms of tetrapyrrole macroheterocyclic ligands (porphyrins, their inverted and N-substituted analogs, and corroles). The temperature ranges of the destruction of porphyrinium acetates and trifluoroacetates, the enthalpies of evaporation of acid molecules from the crystalline phase, and the composition of cationic salts are calculated. The structures of protonated forms of macrocycles are optimized. The energies of porphyrin–acid interaction and the values of charge transfer during the formation of bonds are calculated.
Author information
- Research Institute of Macroheterocyclic Compounds, Ivanovo State University of Chemistry and Technology, 153000, Ivanovo, RussiaA. E. Likhonina, F. K. Morshnev, E. L. Kritskii, T. V. Kudayarova & D. B. Berezin
- Krestov Institute of Solution Chemistry, Russian Academy of Sciences, 153045, Ivanovo, RussiaM. A. Krest’yaninov
References
- The Porphyrin Handbook, Ed. by K. M. Kadish, K. M. Smith, and R. Guilard (Academic, New York, CA, 2000), Vol. 2.
- J. Mack, N. Kobayashi, and Z. Shen, in Handbook of Porphyrin Science, Ed. by K. M. Kadish, K. M. Smith, and R. Guilard (Academic, New York, 2013), Vol. 23, pp. 109, 281.
- R. Paolesse, Applications of Porphyrinoids (Springer, New York, 2014).
- A. V. Kustov and M. B. Berezin, J. Chem. Eng. Data 58, 2502 (2013). https://doi.org/10.1021/je400388j
- A. V. Kustov, N. L. Smirnova, D. B. Berezin, and M. B. Berezin, J. Chem. Thermodyn. 89, 123 (2015). https://doi.org/10.1016/j.jct.2015.05.016
- A. V. Kustov, N. L. Smirnova, D. B. Berezin, and M. B. Berezin, J. Chem. Thermodyn. 83, 104 (2015). https://doi.org/10.1016/j.jct.2014.12.013
- V. G. Andrianov, D. B. Berezin, and O. V. Malkova, in Advances in Porphyrin Chemistry (SPbGU, St. Petersburg, 2001), Vol. 3, p. 107 [in Russian].
- A. Rosa, G. Ricciardi, and E. J. Baerends, J. Porphyr. Phthalocian. 10, 381 (2006).
- M. Presselt, W. Dehaen, W. Maes, A. Klamt, T. Martinez, W. J. D. Beenken, and M. Kruk, Phys. Chem. Chem. Phys. 17, 14096 (2015). https://doi.org/10.1039/C5CP01808K
- A. V. Kustov, S. O. Kruchin, N. L. Smirnova, and D. B. Berezin, Macroheterocycles 9, 373 (2016). https://doi.org/10.6060/mhc160647k
- B. D. Berezin, V. G. Andrianov, and D. B. Berezin, Koord. Khim. 20, 350 (1994).
- D. B. Berezin, Doctoral (Chem.) Dissertation (Ivanovo State Chem. Technol. Univ., Ivanovo, 2007).
- O. A. Petrov, Russ. J. Gen. Chem. 83, 1136 (2013). https://doi.org/10.1134/S1070363213060224
- D. B. Berezin and D. R. Karimov, Macroheterocycles 2, 42 (2009).
- V. S. Chirvony, A. van Hoek, V. A. Galievsky, et al., J. Phys. Chem. 104, 9909 (2000).
- D. B. Berezin, V. G. Andrianov, A. S. Semeykin, and M. B. Berezin, Russ. J. Gen. Chem. 70, 1453 (2000).
- D. B. Berezin, D. R. Karimov, and M. B. Berezin, Russ. J. Phys. Chem. A 87, 593 (2013). https://doi.org/10.1134/S0036024413040055
- D. B. Berezin and M. A. Krest’yaninov, Russ. J. Struct. Chem. 55, 822 (2014). https://doi.org/10.1134/S0022476614050047
- D. B. Berezin, A. E. Talanova, I. N. Serov, A. S. Semeikin, and M. A. Krest’yaninov, Russ. J. Phys. Chem. A 90, 1948 (2016). https://doi.org/10.1134/S0036024416100058
- D. B. Berezin, D. R. Karimov, A. S. Semeikin, and V. P. Barannikov, Russ. J. Phys. Chem. A 85, 2171 (2011). https://doi.org/10.1134/S0036024411120041
- D. B. Berezin, D. R. Karimov, and A. V. Kustov, Corroles and their Derivatives: Synthesis, Properties, Possibility for Practical Application (Lenand, Moscow, 2018) [in Russian].
- D. B. Berezin, V. G. Andrianov, and A. S. Semeikin, Opt. Spectrosc. 80, 554 (1996).
- L. Latos-Grazyński, Inorg. Chem. 24, 1681 (1985). https://doi.org/10.1021/ic00205a018
- B. Koszarna and D. T. Gryko, Org. Chem. 71, 3707 (2006). https://doi.org/10.1021/jo060007k
- G. R. Geier III and J. S. Lindsey, Org. Lett. 1, 1455 (1999). https://doi.org/10.1021/ol9910114
- K. Burger, Experimental Methods for Investigation of Solvation, Ionic and Complex Formation Reactions in Nonaqueous Solutions (Akademiai Klado, Budapest, 1982).
- V. P. Barannikov, A. I. Vyugin, E. V. Antina, and G. A. Krestov, Thermochim. Acta 169, 103 (1990).
- M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, et al., Gaussian 09, Revision D.01 (Gaussian Inc., Wallingford CT, 2009).
- R. Ditchfield, W. J. Hehre, and J. A. Pople, J. Chem. Phys. 54, 724 (1971).
- F. Weinhold, J. Mol. Struct.: THEOCHEM 398–399, 181 (1997).
- E. D. Glendening, A. E. Reed, and F. Weinhold, NBO 3.0 Program Manual (Univ. of Wisconsin, Madison, 1998).
- I. V. Alabugin, M. Manoharan, S. Peabody, and F. Weinhold, J. Am. Chem. Soc. 125, 5973 (2003). https://doi.org/10.1021/ja034656e
- I. V. Sazanovich, A. van Hoek, A. Yu. Panarin, et al., J. Porphyr. Phthalocian. 9, 59 (2005). https://doi.org/10.1142/S1088424605000113
- D. B. Berezin, I. A. Mal’tsev, A. S. Semeikin, and V. L. Bolotin, Russ. J. Phys. Chem. A 79, 1980 (2005).
- D. B. Berezin, N-Substituted Porphyrinoids: Structure, Spectroscopy, Reactivity (LAP Lambert, Saarbrucken, 2012).
- R. Sakashita, M. Ishida, and H. Furuta, J. Phys. Chem. A 119, 1013 (2015). https://doi.org/10.1021/jp512229k
- V. B. Sheinin, O. M. Kulikova, V. V. Aleksandriiskii, and O. I. Koifman, Macroheterocycles 9, 353 (2016). https://doi.org/10.6060/mhc161067s
- D. B. Berezin, Vu Thi Thao, A. A. Azorina, O. V. Shukhto, S. S. Guseinov, and N. M. Berezina, Russ. J. Inorg. Chem. 60, 1267 (2015).
- D. B. Berezin, O. V. Shukhto, Vu Thi Thao, B. D. Berezin, Russ. J. Inorg. Chem. 59, 1522 (2014). https://doi.org/10.1134/S0036023614120067