Intramolecular Hydrogen Bonding and Electronic Structure of Thiadiazole Annulated Hemihexaphyrazine

Arseniy A. Otlyotov,^@ Anton P. Merlyan,Vladimir V. Veretennikov, Alexander E. Pogonin, Evgeny N. Ivanov, Yana E. Filippova, Yuriy A. Zhabanov,^@ and Mikhail K. Islyaikin^@

Dedicated to Professor Oleg Aleksandrovich Golubchikov on the occasion of his 70-th birthday

Institute of Macroheterocycles, Ivanovo State University of Chemistry and Technology (ISUCT), 153000 Ivanovo, Russian Federation

^@Corresponding authors E-mails: arseney_otlyotov@mail.ru, zhabanov@gmail.com, islyaikin@isuct.ru

DOI: 10.6060/mhc180175o

Macroheterocycles 2018 11(1) 67-72

Different tautomeric structures of thiadiazole annelated hemihexaphyrazine (TDAHHp) were considered using DFT in B3LYP/pcseg-2 approximation. Energetics of the intramolecular hydrogen bonding was quantitatively estimated by means of NBO and AIM calculations and according to the NBO analysis results, the most energetically favorable tautomer of TDAHHp surprisingly turned out to possess the lowest total H-bond stabilization energy. The results are compared with that for the previously studied hemihexaphyrazine – 2,3,5,10,12,13,15,20,22,23,25,30-dodecaazahexaphyrin (C₃₀H₁₅N₁₅S₃). Electronic absorption and infrared spectra were simulated for the most favorable tautomer of TDAHHp.

References:

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1. Strenalyuk T., Samdal S., Volden H.V. J. Phys. Chem. A 2008, 112(21), 4853–4860.
https://doi.org/10.1021/jp801284c

2. Stępień M., Latos-Grażyński L. Aromaticity and Tautomerism in Porphyrins and Porphyrinoids. In: Aromaticity in Heterocyclic Compounds (Krygowski T.M., Cyrański M.K., Eds.) Berlin, Heidelberg: Springer, 2009. p. 83–153.
https://doi.org/10.1007/978-3-540-68343-8_3

3. Zakharov A.V., Stryapan M.G., Islyaikin M.K. J. Mol. Struct.: THEOCHEM 2009, 906(1-3), 56–62.
https://doi.org/10.1016/j.theochem.2009.03.030

4. Zakharov A.V., Shlykov S.A., Danilova E.A., Krasnov A.V., Islyaikin M.K., Girichev G.V. Phys. Chem. Chem. Phys. 2009, 11(38), 8570–8579.
https://doi.org/10.1039/b905436g

5. Zhabanov Y.A., Zakharov A.V., Shlykov S.A., Trukhina O.N., Danilova E.A., Koifman O.I., Islyaikin M.K. J. Porphyrins Phthalocyanines 2013, 17(03), 220–228.
https://doi.org/10.1142/S1088424613500144

6. Cirera B., Trukhina O., Björk J., Bottari G., Rodríguez-Fernández J., Martin-Jimenez A., Islyaikin M.K., Otero R., Gallego J.M., Miranda R., Torres T., Ecija D. J. Am. Chem. Soc. 2017, 139(40), 14129–14136.
https://doi.org/10.1021/jacs.7b06406

7. Vogt N., Savelyev D.S., Giricheva N.I., Islyaikin M.K., Girichev G.V. J. Phys. Chem. A 2016, 120(44), 8853–8861.
https://doi.org/10.1021/acs.jpca.6b08241

8. Frisch M.J., Trucks G.W., Schlegel H.B., et al., Gaussian 09, Revision D.01 Gaussian, Inc., Wallingford CT, 2016.

9. Becke A.D. J. Chem. Phys. 1993, 98(7), 5648–5652.
https://doi.org/10.1063/1.464913

10. Lee C., Yang W., Parr R.G. Phys. Rev. B 1988, 37(2), 785–789.
https://doi.org/10.1103/PhysRevB.37.785

11. Vosko S.H., Wilk L., Nusair M. Can. J. Phys. 1980, 58(8), 1200–1211.
https://doi.org/10.1139/p80-159

12. Jensen F. J. Chem. Theory Comput. 2014, 10(3), 1074–1085.
https://doi.org/10.1021/ct401026a

13. Glendening E.D., Reed A.E., Carpenter J.E., Weinhold F. NBO Version 3.1.

14. Keith T.A. AIMAll (Version 16.01.09) TK Gristmill Software, Overland Park KS, USA, 2017. (aim.tkgristmill.com).

15. Granovsky A.A. Firefly version 8. www http://classic.chem.msu.su/gran/firefly/index.html.

16. Schmidt M.W., Baldridge K.K., Boatz J.A., Elbert S.T., Gordon M.S., Jensen J.H., Koseki S., Matsunaga N., Nguyen K.A., Su S., Windus T.L., Dupuis M., Montgomery J.A. J. Comput. Chem. 1993, 14(11), 1347–1363.
https://doi.org/10.1002/jcc.540141112

17. Zhurko G.A. Chemcraft – graphical program for visualization of quantum chemistry computations. https://chemcraftprog.com.

18. Espinosa E., Molins E., Lecomte C. Chem. Phys. Lett. 1998, 285(3), 170–173.
https://doi.org/10.1016/S0009-2614(98)00036-0

19. Vishnevskiy Yu.V., Zhabanov Yu.A. J. Phys. Conf. Ser. 2015, 633(1), 012076.
https://doi.org/10.1088/1742-6596/633/1/012076

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Intramolecular Hydrogen Bonding and Electronic Structure of Thiadiazole Annulated Hemihexaphyrazine

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