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ISSN 1998-9539

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
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.


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