zhpsЖурнал прикладной спектроскопииZhurnal Prikladnoii Spektroskopii0514-7506B. I. Stepanov Institute of Physics of the National Academy of Scienceszhps-2348Research ArticleАННОТАЦИИ АНГЛОЯЗЫЧНЫХ СТАТЕЙABSTRACTS ENGLISH-LANGUAGE ARTICLESСтруктурные, спектроскопические и электронные свойства триазоксидаExperimental and Theoretical Investigations on Structural, Spectroscopic and Electronic Properties of TriazoxideGökceH.GökceH.

Гиресун 

Giresun 

halil.gokce@giresun.edu.trBahçeliS.BahçeliS.

Анкара 

Ankara 

halilgokce.hg@gmail.comПрофессиональное училище медицинских услуг, Университет ГиресунаТурцияVocational School of Health Services, Department of Medical Services and Techniques, Giresun UniversityTurkeyУниверситет Турецкой авиационной ассоциацииТурцияFaculty of Aeronautics and Astronautics, Department of Astronautical Engineering, Turkish Aeronautical Association UniversityTurkey20260809202693457013Copyright © Gökce H., Bahçeli S., 20262026Gökce H., Bahçeli S.Gökce H., Bahçeli S.Данная работа распространяется под лицензией Creative Commons Attribution 4.0.This work is licensed under a Creative Commons Attribution 4.0 License.https://zhps.ejournal.by/jour/article/view/2348

Триазоксид как фунгицид экспериментально охарактеризован с помощью ИК-спектроскопии с преобразованием Фурье (FTIR), спектроскопии ЯМР 1H/13C и УФ-видимой спектроскопии. Теоретическое моделирование проведено на вычислительном уровне DFT/B3LYP/6-311++G(df,pd). Исследована корреляция между экспериментальными и рассчитанными спектральными данными. Конформационный анализ использован для получения наиболее стабильной молекулярной геометрии. Вычисления проведены для двух наиболее стабильных конформационных форм (C1 и C2) триазоксида. Колебательные частоты и отнесения помогли определить молекулярные колебательные движения. Выявлено влияние делокализации электронов в π-системах триазоксида на его молекулярную структуру и некоторые колебательные частоты. Результаты ЯМР-спектроскопии проанализированы с помощью метода GIAO. Внутримолекулярные электронные переходы, соответствующие УФ-видимой спектроскопии. Длины волн определены с помощью моделирования локализации электронов в HOMO/LUMO. Плотность электронов в занятых/вакантных молекулярных орбиталях исследована с помощью анализа плотности состояний.

Triazoxide as a fungicide was experimentally characterized via the help of the FTIR, 1H/13C NMR chemical shifts and UV-Vis spectroscopies. Theoretical modeling was performed using the DFT/B3LYP/6- 311++G(df,pd) computational level. The correlation between experimental and computed spectral data was investigated. The conformational analysis was used to obtain the most stable molecular geometry. Computational studies were performed for the two most stable conformational forms (C1 and C2) of triazoxide. The vibrational frequencies and assignments helped to determine the molecular vibrational motions. The effect of electron delocalization within the π-systems of triazoxide on its molecular structure and some vibrational wavenumbers was uncovered. The computational NMR results were analyzed with the GIAO method. The intra-molecular electronic transitions corresponding to the UV-Vis wavelengths were elucidated with simulations of the HOMO/LUMO electron localizations. The electron densities within the occupied/unoccupied molecular orbitals were investigated with the density of states analysis.

триазоксидконформационный анализмолекулярная спектроскопияанализ HOMO/LUMOанализ плотности состоянийtriazoxideconformational analysismolecular spectroscopyHOMO/LUMO analysisdensity of states analysisReferencesS. Cascioferro, B. Parrino, V. Spano, A. Carbone, A. Montalbano, P. Barraja, P. Diana, G. Cirrincione, Eur. J. Med. Chem., 142, 328–375 (2017).S. Cascioferro, B. Parrino, V. Spano, A. Carbone, A. Montalbano, P. Barraja, P. Diana, G. Cirrincione, Eur. J. Med. Chem., 142, 328–375 (2017).C.-I. Lee, C.-M. Huang, W.-H. Huang, A.-R. Lee, Anti-Cancer Agents Med. Chem., 14, No. 10, 1428–1446 (2014).C.-I. Lee, C.-M. Huang, W.-H. Huang, A.-R. Lee, Anti-Cancer Agents Med. Chem., 14, No. 10, 1428–1446 (2014).J. K. Horner, D. W. Henry, J. Med. Chem., 11, No. 5, 946–949 (1968).J. K. Horner, D. W. Henry, J. Med. Chem., 11, No. 5, 946–949 (1968).B. A. Regan, J. W. Hanifin, M. J. Landes, A. C. Osterberg, G. J. Patel, D. N. Ridge, A. E. Sloboda, S. A. Lang Jr., J. Pharm. Sci., 69, No. 7, 789–793 (1980).B. A. Regan, J. W. Hanifin, M. J. Landes, A. C. Osterberg, G. J. Patel, D. N. Ridge, A. E. Sloboda, S. A. Lang Jr., J. Pharm. Sci., 69, No. 7, 789–793 (1980).E. Polmickaite-Smirnova, J. Sarlauskas, K. Krikstopaitis, Z. Luksiene, Z. Staniulyte, Z. Anusevicius, Appl. Sci., 10, No. 12, 4062 (2020).E. Polmickaite-Smirnova, J. Sarlauskas, K. Krikstopaitis, Z. Luksiene, Z. Staniulyte, Z. Anusevicius, Appl. Sci., 10, No. 12, 4062 (2020).E. M. Zeman, J. M. Brown, M. J. Lemmon, V. K. Hirst, W. W. Lee, Int. J. Rad. Oncol. Biol. Phys., 12, No. 7, 1239–1242 (1986).E. M. Zeman, J. M. Brown, M. J. Lemmon, V. K. Hirst, W. W. Lee, Int. J. Rad. Oncol. Biol. Phys., 12, No. 7, 1239–1242 (1986).D. R. Gandara, P. N. Lara Jr., Z. Goldberg, Q. T. Le, P. C. Mack, D. H. Lau, P. H. Gumerlock, Sem. Oncol., 29, No. 1, 102–109 (2002).D. R. Gandara, P. N. Lara Jr., Z. Goldberg, Q. T. Le, P. C. Mack, D. H. Lau, P. H. Gumerlock, Sem. Oncol., 29, No. 1, 102–109 (2002).W. A. Denny, Anti-Cancer Agents Med. Chem., 4, No. 5, 395–399 (2004).W. A. Denny, Anti-Cancer Agents Med. Chem., 4, No. 5, 395–399 (2004).S. B. Reddy, S. K. Williamson, Expert Opin. Invest. Drugs., 18, No. 1, 77–87 (2009).S. B. Reddy, S. K. Williamson, Expert Opin. Invest. Drugs., 18, No. 1, 77–87 (2009).D. P. Chong, J. Chin. Chem. Soc., 63, No. 1, 109–120 (2016).D. P. Chong, J. Chin. Chem. Soc., 63, No. 1, 109–120 (2016).N. Ahmadinejad, M. T. Tari, Russ. J. Phys. Chem. A, 89, No. 11, 2155–2157 (2015).N. Ahmadinejad, M. T. Tari, Russ. J. Phys. Chem. A, 89, No. 11, 2155–2157 (2015).L.-C. Li, D. Zha, Y.-Q. Zhu, M.-H. Xu, N.-B. Wong, Chem. Phys. Lett., 408, No. 4-6, 329–334 (2005).L.-C. Li, D. Zha, Y.-Q. Zhu, M.-H. Xu, N.-B. Wong, Chem. Phys. Lett., 408, No. 4-6, 329–334 (2005).S. Avarand, A. Morsali, M. M. Heravi, S. A. Beyramabadi, Quim. Nova, 41, No. 1, 49–54 (2018).S. Avarand, A. Morsali, M. M. Heravi, S. A. Beyramabadi, Quim. Nova, 41, No. 1, 49–54 (2018).J. Romero, T. Maihom, P. Limao-Vieira, M. Probst, J. Mol. Model., 27, 177 (2021).J. Romero, T. Maihom, P. Limao-Vieira, M. Probst, J. Mol. Model., 27, 177 (2021).J. Sarlauskas, K. Tulaite, J. Tamuliene, J. Mol. Model., 28, 96 (2022).J. Sarlauskas, K. Tulaite, J. Tamuliene, J. Mol. Model., 28, 96 (2022).S. Hillebrand, K. Tietjen, J.-L. Zundel, In: Fungicides with Unknown Mode of Action, 2, Eds. P. Jeschke, M. Witschel, W. Krämer, U. Schirmer, Wiley–VCH Verlag GmbH & Co. KGaA, 911–932 (2019).S. Hillebrand, K. Tietjen, J.-L. Zundel, In: Fungicides with Unknown Mode of Action, 2, Eds. P. Jeschke, M. Witschel, W. Krämer, U. Schirmer, Wiley–VCH Verlag GmbH & Co. KGaA, 911–932 (2019).S. Dutzmann, BCPC Monogr., 57, 85–89 (1994).S. Dutzmann, BCPC Monogr., 57, 85–89 (1994).C. Kucuk, S. Yurdakul, B. Erdem, Chem. Pap., 76, 2833–2854 (2022).C. Kucuk, S. Yurdakul, B. Erdem, Chem. Pap., 76, 2833–2854 (2022).M. Faris, H. E. Bostancı, İ. Özcan, M. Öztürk, Ü. M. Koçyiğit, T. Erdoğan, H. Tahtaci, ACS Omega, 9, No. 19, 20937–20956 (2024).M. Faris, H. E. Bostancı, İ. Özcan, M. Öztürk, Ü. M. Koçyiğit, T. Erdoğan, H. Tahtaci, ACS Omega, 9, No. 19, 20937–20956 (2024).D. Dwarakanath, Y. N. Nayak, A. Kulal, S. Pandey, K. S. R. Pai, S. L. Gaonkar, Sci. Rep., 15, No. 1, 9809 (2025).D. Dwarakanath, Y. N. Nayak, A. Kulal, S. Pandey, K. S. R. Pai, S. L. Gaonkar, Sci. Rep., 15, No. 1, 9809 (2025).A. D. Becke, J. Chem. Phys., 98, No. 7, 5648–5652 (1993).A. D. Becke, J. Chem. Phys., 98, No. 7, 5648–5652 (1993).C. Lee, W. Yang, R. G. Parr, Phys. Rev. B, 37, No. 2, 785–789 (1988).C. Lee, W. Yang, R. G. Parr, Phys. Rev. B, 37, No. 2, 785–789 (1988).M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, et al., Gaussian 09, Revision C.01, Gaussian, Inc., Wallingford, CT (2009).M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, et al., Gaussian 09, Revision C.01, Gaussian, Inc., Wallingford, CT (2009).R. Dennington, T. Keith, J. Millam, GaussView, Version 5, Semichem Inc., Shawnee Mission, KS (2009).R. Dennington, T. Keith, J. Millam, GaussView, Version 5, Semichem Inc., Shawnee Mission, KS (2009).P. M. Wojciechowski, D. Michalska, Spectrochim. Acta A: Mol. Biomol. Spectrosc., 68, No. 3, 948–955 (2007).P. M. Wojciechowski, D. Michalska, Spectrochim. Acta A: Mol. Biomol. Spectrosc., 68, No. 3, 948–955 (2007).M. H. Jamr’oz, Vibrational Energy Distribution Analysis VEDA4, Warsaw (2004).M. H. Jamr’oz, Vibrational Energy Distribution Analysis VEDA4, Warsaw (2004).M. H. Jamr’oz, Spectrochim. Acta A: Mol. Biomol. Spectrosc., 114, 220–230 (2013).M. H. Jamr’oz, Spectrochim. Acta A: Mol. Biomol. Spectrosc., 114, 220–230 (2013).E. Cancès, B. Mennucci, J. Tomasi, J. Chem. Phys., 107, No. 8, 3032–3041 (1997).E. Cancès, B. Mennucci, J. Tomasi, J. Chem. Phys., 107, No. 8, 3032–3041 (1997).F. London, J. Phys. Radium, 8, No. 10, 397–409 (1937).F. London, J. Phys. Radium, 8, No. 10, 397–409 (1937).R. Ditchfield, Mol. Phys., 27, No. 4, 789–807 (1974).R. Ditchfield, Mol. Phys., 27, No. 4, 789–807 (1974).K. Wolinski, J. F. Hinton, P. Pulay, J. Am. Chem. Soc., 112, No. 23, 8251–8260 (1990).K. Wolinski, J. F. Hinton, P. Pulay, J. Am. Chem. Soc., 112, No. 23, 8251–8260 (1990).E. Runge, E. K. U. Gross, Phys. Rev. Lett., 52, No. 12, 997–1000 (1984).E. Runge, E. K. U. Gross, Phys. Rev. Lett., 52, No. 12, 997–1000 (1984).S. Slassi, O. Stetsiuk, A. Amine, M. Aarjane, A. El-Ghayoury, H. Zouihric, K. Yamni, IUCrData, 4, x190036 (2019).S. Slassi, O. Stetsiuk, A. Amine, M. Aarjane, A. El-Ghayoury, H. Zouihric, K. Yamni, IUCrData, 4, x190036 (2019).T. Fuchs, C. L. Barnes, K. S. Gates, J. Chem. Crystallogr., 31, No. 7-8, 387–391 (2001).T. Fuchs, C. L. Barnes, K. S. Gates, J. Chem. Crystallogr., 31, No. 7-8, 387–391 (2001).V. Junnotula, U. Sarkar, C. L. Barnes, P. K. Thallapally, K. S. Gates, J. Chem. Crystallogr., 36, No. 9, 557–561 (2006).V. Junnotula, U. Sarkar, C. L. Barnes, P. K. Thallapally, K. S. Gates, J. Chem. Crystallogr., 36, No. 9, 557–561 (2006).C. Karaca, A. Atac, M. Karabacak, Spectrochim. Acta A: Mol. Biomol. Spectrosc., 140, 85–95 (2015).C. Karaca, A. Atac, M. Karabacak, Spectrochim. Acta A: Mol. Biomol. Spectrosc., 140, 85–95 (2015).J. Lorenc, A. Zając, J. Janczak, R. Lisiecki, J. Hanuza, K. Hermanowicz, J. Mol. Struct., 1265, 133372 (2022).J. Lorenc, A. Zając, J. Janczak, R. Lisiecki, J. Hanuza, K. Hermanowicz, J. Mol. Struct., 1265, 133372 (2022).P. Godlewska, W. Sasiadek, E. Kucharska, P. Ropuszyńska-Robak, L. Dymińska, J. Janczak, R. Lisiecki, M. Ptak, J. Hanuza, Spectrochim. Acta A: Mol. Biomol. Spectrosc., 305, 123426 (2024).P. Godlewska, W. Sasiadek, E. Kucharska, P. Ropuszyńska-Robak, L. Dymińska, J. Janczak, R. Lisiecki, M. Ptak, J. Hanuza, Spectrochim. Acta A: Mol. Biomol. Spectrosc., 305, 123426 (2024).V. H. Rezvan, Results Chem., 7, 101437 (2024).V. H. Rezvan, Results Chem., 7, 101437 (2024).N. B. Colthup, L. H. Daly, E. Wiberley, Introduction to Infrared and Raman Spectroscopy, Academic Press, New York (1964).N. B. Colthup, L. H. Daly, E. Wiberley, Introduction to Infrared and Raman Spectroscopy, Academic Press, New York (1964).L. J. Bellamy, The Infrared Spectra of Complex Molecules, 3rd ed., Wiley, New York (1975).L. J. Bellamy, The Infrared Spectra of Complex Molecules, 3rd ed., Wiley, New York (1975).J. B. Lambert, H. F. Shurvell, R. G. Cooks, Introduction to Organic Spectroscopy, Macmillan Publish, New York (1987).J. B. Lambert, H. F. Shurvell, R. G. Cooks, Introduction to Organic Spectroscopy, Macmillan Publish, New York (1987).R. M. Silverstein, F. X. Webster, Spectroscopic Identification of Organic Compound, 6nd ed., John Willey & Sons, New York (1998).R. M. Silverstein, F. X. Webster, Spectroscopic Identification of Organic Compound, 6nd ed., John Willey & Sons, New York (1998).B. H. Stuart, Infrared Spectroscopy: Fundamentals and Applications, John Willey & Sons, England (2004).B. H. Stuart, Infrared Spectroscopy: Fundamentals and Applications, John Willey & Sons, England (2004).M. Boyd, M. P. Hay, P. D. W. Boyd, Magn. Res. Chem., 44, No. 10, 948–954 (2006).M. Boyd, M. P. Hay, P. D. W. Boyd, Magn. Res. Chem., 44, No. 10, 948–954 (2006).T. Fuchs, G. Chowdhury, C. L. Barnes, K. S. Gates, J. Org. Chem., 66, No. 1, 107–114 (2001).T. Fuchs, G. Chowdhury, C. L. Barnes, K. S. Gates, J. Org. Chem., 66, No. 1, 107–114 (2001).N. M. O’Boyle, A. L. Tenderholt, K. M. Langner, J. Comp. Chem., 29, No. 5, 839–845 (2008).N. M. O’Boyle, A. L. Tenderholt, K. M. Langner, J. Comp. Chem., 29, No. 5, 839–845 (2008).K. Fukui, Science, 218, No. 4574, 747–754 (1982).K. Fukui, Science, 218, No. 4574, 747–754 (1982).R. G. Parr, R. G. Pearson, J. Am. Chem. Soc., 105, No. 26, 7512–7516 (1983).R. G. Parr, R. G. Pearson, J. Am. Chem. Soc., 105, No. 26, 7512–7516 (1983).R. G. Pearson, J. Org. Chem., 54, No. 6, 1430–1432 (1989).R. G. Pearson, J. Org. Chem., 54, No. 6, 1430–1432 (1989).R. G. Parr, L. Szentpaly, S. Liu, J. Am. Chem. Soc., 121, No. 9, 1922–1924 (1999).R. G. Parr, L. Szentpaly, S. Liu, J. Am. Chem. Soc., 121, No. 9, 1922–1924 (1999).P. Geerlings, F. De Proft, W. Langenaeker, Chem. Rev., 103, No. 5, 1793–1873 (2003).P. Geerlings, F. De Proft, W. Langenaeker, Chem. Rev., 103, No. 5, 1793–1873 (2003).C.-G. Zhan, J. A. Nichols, D. A. Dixon, J. Phys. Chem. A, 107, No. 20, 4184–4195 (2003).C.-G. Zhan, J. A. Nichols, D. A. Dixon, J. Phys. Chem. A, 107, No. 20, 4184–4195 (2003).C. U. Kumar, K. G. Krishnan, S. Balachandran, M. V. Pillai, S. Pandiaraj, K. A. Alibrahim, A. N. Alodhayb, A. S. K. Kumar, J. Mol. Struct., 1325, 140961 (2025).C. U. Kumar, K. G. Krishnan, S. Balachandran, M. V. Pillai, S. Pandiaraj, K. A. Alibrahim, A. N. Alodhayb, A. S. K. Kumar, J. Mol. Struct., 1325, 140961 (2025).

The authors declare that there are no conflicts of interest present.