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Simulation of porphyrin-ethanol solvate shell by DFT method

Ivanovo Research Institute of Film Materials and Artificial Leather for Technical Purposes, 153020 Ivanovo, Russia

Research Institute of Macroheterocyclic Compounds, Ivanovo State University of Chemistry and Technology, Sheremetievskiy Avenue 7, 153000 Ivanovo, Russia

International Research Laboratory of Nanomaterials, Ivanovo State University of Chemistry and Technology, Sheremetievskiy Avenue 7, 153000 Ivanovo, Russia

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Irina P. Trifonova

Research Institute of Macroheterocyclic Compounds, Ivanovo State University of Chemistry and Technology, Sheremetievskiy Avenue 7, 153000 Ivanovo, Russia

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Vladimir A. Burmistrov

Research Institute of Macroheterocyclic Compounds, Ivanovo State University of Chemistry and Technology, Sheremetievskiy Avenue 7, 153000 Ivanovo, Russia

E-mail Address: burmistrov@isuct.ru

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, and

Oscar I. Koifman

Research Institute of Macroheterocyclic Compounds, Ivanovo State University of Chemistry and Technology, Sheremetievskiy Avenue 7, 153000 Ivanovo, Russia

International Research Laboratory of Nanomaterials, Ivanovo State University of Chemistry and Technology, Sheremetievskiy Avenue 7, 153000 Ivanovo, Russia

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https://doi.org/10.1142/S1088424615501072Cited by:2 (Source: Crossref)

Abstract

Theoretical studies on porphyrin-ethanol solvates containing from 1 to 8 ethanol molecules have been carried out by density functional theory (DFT) calculations using hybrid (B3LYP) and meta-GGA (M06-L) functionals. It was established that porphirin molecule can be considered as two centered protones acceptor. Specific solvation is at the base of porphyrin-(EtOH)n interactions and results in a distortion of macrocycle planar structure. The nucleophilic solvation energy of the porphirin pyrrole demonstrates dependence on the number of molecules in the ethanol solvate, being the highest for the first two ethanol molecules and decreasing with ethanol association in the solvation shell. Results obtained by this way are in good agreement with data derived from ¹H NMR.

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References

1. (a) Chou JH, Nalwa HS, Kosal ME, Rakow NA and Suslick KS. In The porphyrin Handbook. Applications: past, present and future, Vol. 6, Kadish KM, Smith KM and Guilard R. (Eds.) Academic Press: New York, 2000; pp 43–132. (b) Bottari G, de la Torre G and Torres T. Acc. Chem. Res. 2015; 48: 900–910. Google Scholar
2. Lehninger AL, Nelson DL and Cox MM. Principles of Biochemistry, 2nd edn., New York, 1993; pp. 1090. Google Scholar
3. Kononov VD, Trifonova IP, Alexandriisky VV, Burmistrov VA and Koifman OI. Russ. J. Inorg. Chem. 2009; 54: 460–463. Crossref, Web of Science, Google Scholar
4. Berezin BD, Golubchikov OA and Koifman OI. Russ. J. Phys. Chem. 1974; 12: 2913–2916. Google Scholar
5. Burmistrov VA, Alexandriisky VV, Kononov VD, Trifonova IP, Islyaikin MK, Koifman OI and Syrbu SA. Izv. Vyssh. Uchebn. Zaved. Khim. Khim. Tekhnol. 2008; 51: 53–55. Google Scholar
6. Burmistrov VA, Alexandriisky VV, Kononov VD, Trifonova IP, Koifman OI and Syrbu SA. Izv. Vyssh. Uchebn. Zaved. Khim. Khim. Tekhnol. 2008; 51: 39–42. Google Scholar
7. Becke AD. J. Chem. Phys. 1993; 98: 5648–5652. Crossref, Web of Science, Google Scholar
8. Granovsky AA. Firefly version 8, http://www. classic.chem.msu.su/gran/firefly/index.html. Google Scholar
9. (a) Sousa SF, Fernandes PA and Ramos MJ. J. Phys. Chem. A 2007; 111: 10439–10452. (b) Zhao Y and Truhlar DG. J. Chem. Phys. 2006; 125: 194101-1-194101-18. Google Scholar
10. Valiev M, Bylaska EJ, Govind N, Kowalski K, Straatsma NP, van Dam HJJ, Wang D, Nieplocha J, Apra E, Windus TL and de Jong WA. Comput. Phys. Commun. 2010; 181: 1477–1489. Crossref, Web of Science, Google Scholar
11. Jurko GA. http://www.chemcraftprog.com. Google Scholar
12. http://www.ccdc.cam.ac.uk/Solutions/CSDSystem/Pages/Mercury.aspx. Google Scholar
13. Sousa SF, Fernandes PA and Ramos MJ. J. Phys. Chem. A. 2007; 111: 10439–10452. Crossref, Web of Science, Google Scholar
14. Lavallee DK. Coord. Chem. Rev. 1985; 61: 55–96. Crossref, Web of Science, Google Scholar