zhpsЖурнал прикладной спектроскопииZhurnal Prikladnoii Spektroskopii0514-7506B. I. Stepanov Institute of Physics of the National Academy of Scienceszhps-146Research Article******СИHТЕЗ, ВИБРАЦИОННЫЕ СПЕКТРЫ И МОДЕЛИРОВАНИЕ МЕТОДОМ ТЕОРИИ ФУНКЦИОНАЛА ПЛОТНОСТИ 3-БРОМО-2-МЕТИЛ-5-(4-НИТОФЕНИЛ)ТИОФЕНАSYNTHESIS, VIBRATIONAL SPECTRA, AND DFT SIMULATIONS OF 3-BROMO-2-METHYL-5-(4-NITROPHENYL)THIOPHENEBalakitA. A.BalakitA. A.asim_alsalehi@hotmail.comSertY. .SertY. .noemail@neicon.ruÇırakÇ. .ÇırakÇ. .noemail@neicon.ruSmithK. .SmithK. .noemail@neicon.ruKariukiB. M.KariukiB. M.noemail@neicon.ruEl-HitiG. A.El-HitiG. A.noemail@neicon.ruКолледж фармации, Вавилонский университетCollege of Pharmacy, University of BabylonУниверситет Бозока; Соргунское профессиональное училище, Университет БозокаBozok University; Sorgun Vocational School, Bozok UniversityУниверситет ЭрзинджанаErzincan UniversityШкола химии, Университет КардиффаSchool of Chemistry, Cardiff UniversityКолледж прикладных медицинских наук, Университет короля СаудаCollege of Applied Medical Sciences, King Saud University201710032020845834(1)-834(12)Copyright © Balakit A.A., Sert Y..., Çırak Ç..., Smith K..., Kariuki B.M., El-Hiti G.A., 20202020Balakit A.A., Sert Y..., Çırak Ç..., Smith K..., Kariuki B.M., El-Hiti G.A.Balakit A.A., Sert Y..., Çırak Ç..., Smith K..., Kariuki B.M., El-Hiti G.A.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/146

C помощью реакции Сузуки связывания 4-бром-5-метилтиофен-2-илбороновой кислоты (1) и 4-иоднитробензола синтезировано новое производное тиофена 3-бром-2-метил-5-(4-нитрофенил) тиофен (2). Его структура подтверждена методами ЯМР, масс-спектрометрии низкого и высокого разрешения, ИК-фурье-спектроскопии, рентгеновских исследований кристаллической структуры. Исследованы его экспериментальные ИК-фурье-спектры (4000-400 см-1) и спектры комбинационного рассеяния (4000-100 см-1). Рассчитанные геометрические параметры и частоты колебаний согласуются с экспериментальными данными. Вычислены энергии для высшей занятой и низшей вакантной молекулярных орбиталей, а также другие параметры для соединения 2. Методами B3LYP и HF получены потенциалы ионизации -0.30456 и -0.30501 эВ.

A new thiophene derivative, 3-bromo-2-methyl-5-(4-nitrophenyl)thiophene (2), was synthesized through the Suzuki coupling reaction of 4-bromo-5-methylthiophen-2-ylboronic acid (1) and 4-iodonitrobenzene, and its structure was confirmed by nuclear magnetic resonance (NMR), low and high resolution mass spectrometry (HRMS), Fourier transform infrared spectroscopy (FT-IR), and X-ray investigations of the crystal structure. The FT-IR spectra (4000-400 cm-1), Raman spectra (4000-100 cm-1), and theoretical vibrational frequencies of this new substance were investigated. Its theoretically established geometric parameters and calculated vibrational frequencies are in good agreement with the reported experimental data. The highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energies and other related parameters of the compound were calculated. The ionization potentials given by the B3LYP and HF (Hartree-Fock) methods for this new compound are -0.30456 and -0.30501 eV, respectively.

ИК-фурье-спектроскопияспектр комбинационного рассеяния света3-бром -2-метил-5-(4-нитрофенил)тиофенвибрационные частотыпограничные молекулярные орбиталиFT-IR spectraRaman spectra3-bromo-2-methyl-5-(4-nitrophenyl)thiophenevibrational frequenciesfrontier molecular orbitalReferencesM. Irie, Chem. Rev., 100, 1685-1716(2000).M. Irie, Chem. Rev., 100, 1685-1716(2000).M. Balter, S. Li, J. R. Nilsson, J. Andreasson, U. Pischel, J. Am. Chem. Soc., 135, 10230-10233 (2013).M. Balter, S. Li, J. R. Nilsson, J. Andreasson, U. Pischel, J. Am. Chem. Soc., 135, 10230-10233 (2013).J.-C. Boyer, C-J. Carling, B. D. Gates, N. R. Branda, J. Am. Chem. Soc., 132, 15766-15772(2010).J.-C. Boyer, C-J. Carling, B. D. Gates, N. R. Branda, J. Am. Chem. Soc., 132, 15766-15772(2010).T. C. Pijper, T. Kudernac, W. R. Browne, B. L. Feringa, J. Phys. Chem. C, 117, 17623-17632 (2013).T. C. Pijper, T. Kudernac, W. R. Browne, B. L. Feringa, J. Phys. Chem. C, 117, 17623-17632 (2013).N. Soh, K. Yoshida, H. Nakajima, K. Nakano, T. Imato, T. Fukaminatob, M. Irie, M. Chem. Commun., 5206-5208 (2007). 834-11N. Soh, K. Yoshida, H. Nakajima, K. Nakano, T. Imato, T. Fukaminatob, M. Irie, M. Chem. Commun., 5206-5208 (2007). 834-11Handbook of Organopalladium Chemistry for Organic Synthesis; Ed. E. Negishi, Wiley-Interscience, New York, Part III, 213 (2002).Handbook of Organopalladium Chemistry for Organic Synthesis; Ed. E. Negishi, Wiley-Interscience, New York, Part III, 213 (2002).J. J. Li, G. W. Gribble, Palladium in Heterocyclic Chemistry; Pergamon, Amsterdam (2000).J. J. Li, G. W. Gribble, Palladium in Heterocyclic Chemistry; Pergamon, Amsterdam (2000).J. J. Dong, D. Roy, J. R. Roy, M. Ionita, H. Doucet, Synthesis, 3530-3546 (2011).J. J. Dong, D. Roy, J. R. Roy, M. Ionita, H. Doucet, Synthesis, 3530-3546 (2011).G. Vamvounis, D. Gendron, Tetrahedron Lett.,54, 3785-3787 (2013).G. Vamvounis, D. Gendron, Tetrahedron Lett.,54, 3785-3787 (2013).W. Renjie, P. Shouzhi, L. Gang, C. Bing, Tetrahedron, 69, 5537-5544 (2013).W. Renjie, P. Shouzhi, L. Gang, C. Bing, Tetrahedron, 69, 5537-5544 (2013).K. A. Browne, D. D. Deheyn, G. A. El-Hiti, K. Smith, I. Weeks, J. Am. Chem. Soc., 133, 14637-14648 (2011).K. A. Browne, D. D. Deheyn, G. A. El-Hiti, K. Smith, I. Weeks, J. Am. Chem. Soc., 133, 14637-14648 (2011).K. Smith, G. A. El-Hiti, A. S. Hegazy, Chem. Commun., 46, 2790-2792 (2010).K. Smith, G. A. El-Hiti, A. S. Hegazy, Chem. Commun., 46, 2790-2792 (2010).K. Smith, G. A. El-Hiti, A. C. Hawes, Synthesis, 2047-2052(2003).K. Smith, G. A. El-Hiti, A. C. Hawes, Synthesis, 2047-2052(2003).K. Smith, G. A. El-Hiti, G. Pritchard, A. Hamilton, A. J. Chem. Soc., Perkin Trans. I, 2299-2304 (1999).K. Smith, G. A. El-Hiti, G. Pritchard, A. Hamilton, A. J. Chem. Soc., Perkin Trans. I, 2299-2304 (1999).Y. Sert, A. A. Balakit, N. Öztürk, F. Ucun, G. A. El-Hiti, Spectrochim. Acta A, 131, 502-511 (2014).Y. Sert, A. A. Balakit, N. Öztürk, F. Ucun, G. A. El-Hiti, Spectrochim. Acta A, 131, 502-511 (2014).Y. Sert, F. Ucun, G. A. El-Hiti, K. Smith, A. S. Hegazy, J. Spectrosc., (2016) http://dx.doi.org/10.1155/2016/5396439.Y. Sert, F. Ucun, G. A. El-Hiti, K. Smith, A. S. Hegazy, J. Spectrosc., (2016) http://dx.doi.org/10.1155/2016/5396439.G. M. Sheldrick, Acta Crystallogr., A64, 112-122 (2008).G. M. Sheldrick, Acta Crystallogr., A64, 112-122 (2008).A. Frish, A. B. Nielsen, A. J. Holder, Gauss View User Manual, Gaussian Inc., Pittsburg, PA (2001).A. Frish, A. B. Nielsen, A. J. Holder, Gauss View User Manual, Gaussian Inc., Pittsburg, PA (2001).D. C. Young, Computational Chemistry A Practical Guide for Applying Techniques to Real-World Problems (Electronics), John Wiley and Sons, New York (2001).D. C. Young, Computational Chemistry A Practical Guide for Applying Techniques to Real-World Problems (Electronics), John Wiley and Sons, New York (2001).Gaussian 09, Revision A.1, Gaussian, Wallingford CT (2009).Gaussian 09, Revision A.1, Gaussian, Wallingford CT (2009).M. H. Jamróz, Vibrational Energy Distribution Analysis VEDA 4, Warsaw (2004).M. H. Jamróz, Vibrational Energy Distribution Analysis VEDA 4, Warsaw (2004).M. H. Jamróz, Spectrochim. Acta A, 114, 220-230 (2013).M. H. Jamróz, Spectrochim. Acta A, 114, 220-230 (2013).G. A. El-Hiti, K. Smith, A. A. Balakit, A. Masmali, B. M. Kariuki, Acta Crystallogr., E69, o1385 (2013).G. A. El-Hiti, K. Smith, A. A. Balakit, A. Masmali, B. M. Kariuki, Acta Crystallogr., E69, o1385 (2013).A. Ünal, B. Eren, Spectrochim. Acta A, 114, 129-136 (2013).A. Ünal, B. Eren, Spectrochim. Acta A, 114, 129-136 (2013).M. Karabacak, S. Bilgili, T. Mavis, M. Eskici, A. Atac, Spectrochim. Acta A, 115, 709-718 (2013).M. Karabacak, S. Bilgili, T. Mavis, M. Eskici, A. Atac, Spectrochim. Acta A, 115, 709-718 (2013).W. T. Harrison, C. S. C. Kumar, H. S. Yathirajan, B. V. Ashalatha, B. Narayana, Acta Crystallogr., E66, o2477 (2010).W. T. Harrison, C. S. C. Kumar, H. S. Yathirajan, B. V. Ashalatha, B. Narayana, Acta Crystallogr., E66, o2477 (2010).X. Li, X. Jia, J. Li, Acta Crystallogr., E69, o848 (2013).X. Li, X. Jia, J. Li, Acta Crystallogr., E69, o848 (2013).M. M. Bader, Acta Crystallogr., E65, o2119 (2009).M. M. Bader, Acta Crystallogr., E65, o2119 (2009).M. Akkurt, Ş. P. Yalçın, A. M. Asiri, O. Büyükgüngör, Acta Crystallogr., E64, o923(2008).M. Akkurt, Ş. P. Yalçın, A. M. Asiri, O. Büyükgüngör, Acta Crystallogr., E64, o923(2008).Z. H. Choban, M. Hanif, M. N. Tahir, Acta Crystallogr., E65, o117 (2009).Z. H. Choban, M. Hanif, M. N. Tahir, Acta Crystallogr., E65, o117 (2009).G. Varsayani, Assignments for Vibrational Spectra of Seven Hundred Benzene Derivatives, vols. 1 and 2, Academic Kiado, Budapest (1973).G. Varsayani, Assignments for Vibrational Spectra of Seven Hundred Benzene Derivatives, vols. 1 and 2, Academic Kiado, Budapest (1973).M. Jag, Organic Spectroscopy-Principles and Applications, 2nd ed., Narosa Publishing House, New Delhi (2001).M. Jag, Organic Spectroscopy-Principles and Applications, 2nd ed., Narosa Publishing House, New Delhi (2001).V. Balachandran, A. Janaki, A. Nataraj, Spectrochim. Acta A, 118, 321-330 (2014).V. Balachandran, A. Janaki, A. Nataraj, Spectrochim. Acta A, 118, 321-330 (2014).J. Svoboda, J. Sedlacek, J. Zednik, G. Dvorakova, O. Trhlikova, D. Redrova, H. Balcar, J. Vohlidal, J. Pol. Sci., 46, 2776-2787 (2008).J. Svoboda, J. Sedlacek, J. Zednik, G. Dvorakova, O. Trhlikova, D. Redrova, H. Balcar, J. Vohlidal, J. Pol. Sci., 46, 2776-2787 (2008).C. I. Sainz-Diaz, M. Francisco-Marquez, A. Vivier-Bunge, Theor. Chem. Acc., 125, 83-95 (2010).C. I. Sainz-Diaz, M. Francisco-Marquez, A. Vivier-Bunge, Theor. Chem. Acc., 125, 83-95 (2010).T. D. Klots, R. D. Chirico, W. V. Steele, Spectrochim. Acta A, 5, 765-795 (1994).T. D. Klots, R. D. Chirico, W. V. Steele, Spectrochim. Acta A, 5, 765-795 (1994).M. Karabacak, C. Karaca, A. Atac, M. Eskici, A. Karanfil, E. Köse, Spectrochim. Acta A, 97, 556-567 (2012).M. Karabacak, C. Karaca, A. Atac, M. Eskici, A. Karanfil, E. Köse, Spectrochim. Acta A, 97, 556-567 (2012).N. P. G. Roeges, A Guide to the Complete Interpretation of Infrared Spectra of Organic Structures, Wiley, New York (1994).N. P. G. Roeges, A Guide to the Complete Interpretation of Infrared Spectra of Organic Structures, Wiley, New York (1994).N. B. Colthup, L. H. Daly, S. E. Wiberly, Introduction to Infrared and Raman Spectroscopy, 3rd ed., Academic Press, Boston (1990).N. B. Colthup, L. H. Daly, S. E. Wiberly, Introduction to Infrared and Raman Spectroscopy, 3rd ed., Academic Press, Boston (1990).B. Smith, Infrared Spectral Interpretation, A systematic Approach, CRP Press, Washington, DC (1999).B. Smith, Infrared Spectral Interpretation, A systematic Approach, CRP Press, Washington, DC (1999).A. Kumar, V. Deval, P. Tandom, A. Gupta, E. D. D'silva, Spectrochim. Acta A, 130, 41-53 (2014).A. Kumar, V. Deval, P. Tandom, A. Gupta, E. D. D'silva, Spectrochim. Acta A, 130, 41-53 (2014).S. Periandy, S. Mohan, Proc. Natl. Acad. Sci. India, 68(A), III (1998).S. Periandy, S. Mohan, Proc. Natl. Acad. Sci. India, 68(A), III (1998).V. R. Dani, Organic Spectroscopy, Tata-MacGraw Hill Publishing Company, New Delhi, p. 139 (1995).V. R. Dani, Organic Spectroscopy, Tata-MacGraw Hill Publishing Company, New Delhi, p. 139 (1995).E. Fereyduni, M. K. Rofouei, M. Kamae, S. Ramalingam, S. M. Sharifkhani, Spectrochim. Acta A, 90, 193-201 (2012).E. Fereyduni, M. K. Rofouei, M. Kamae, S. Ramalingam, S. M. Sharifkhani, Spectrochim. Acta A, 90, 193-201 (2012).H. Abdel-Shafy, H. Perlmutter, H. Kimmel, J. Mol. Struct., 42, 37-49 (1977).H. Abdel-Shafy, H. Perlmutter, H. Kimmel, J. Mol. Struct., 42, 37-49 (1977).V. K. Kumar, V. Balachandran, Spectrochim. Acta A, 61, 1811-1819 (2005).V. K. Kumar, V. Balachandran, Spectrochim. Acta A, 61, 1811-1819 (2005).A. Kovacs, G. Keresztury, V. Izvekov, Chem. Phys., 253, 193-204 (2000).A. Kovacs, G. Keresztury, V. Izvekov, Chem. Phys., 253, 193-204 (2000).K. Sarojini, H. Krishnan, C. C. Kanakam, S. Muthu, Spectrochim. Acta A, 108, 159-170 (2013). 834-12K. Sarojini, H. Krishnan, C. C. Kanakam, S. Muthu, Spectrochim. Acta A, 108, 159-170 (2013). 834-12N. Sundaraganesan, S. Ilakiamani, H. Saleem, S. Mohan, Indian J. Pure Appl. Phys., 42, 585-590 (2004).N. Sundaraganesan, S. Ilakiamani, H. Saleem, S. Mohan, Indian J. Pure Appl. Phys., 42, 585-590 (2004).S. Ayyapan, N. Sundaraganesan, M. Kurt, T. R. Sertbakan, M. Ozduran, J. Raman Spectrosc., 41, 1379-1387 (2010).S. Ayyapan, N. Sundaraganesan, M. Kurt, T. R. Sertbakan, M. Ozduran, J. Raman Spectrosc., 41, 1379-1387 (2010).K. Chaitanya, Spectrochim. Acta A, 86, 159-173 (2012).K. Chaitanya, Spectrochim. Acta A, 86, 159-173 (2012).E. Kavitha, N. Sundaraganesan, S. Sebastian, Indian J. Pure Appl. Phys., 48, 20-30 (2010).E. Kavitha, N. Sundaraganesan, S. Sebastian, Indian J. Pure Appl. Phys., 48, 20-30 (2010).A. Jayaprakash, V. Arjunan, S. Mohan, Spectrochim. Acta A, 81, 620-630 (2011).A. Jayaprakash, V. Arjunan, S. Mohan, Spectrochim. Acta A, 81, 620-630 (2011).S. Subashchandrabose, H. Saleem, Y. Erdogdu, G. Rajarajan, V. Thanikachalam, Spectrochim. Acta A, 82, 260-269 (2011).S. Subashchandrabose, H. Saleem, Y. Erdogdu, G. Rajarajan, V. Thanikachalam, Spectrochim. Acta A, 82, 260-269 (2011).T. Vijayakumar, I. Hubert Joe, C. P. R. Nair, V. S. Jayakumar, Chem. Phys., 343, 83-99 (2008).T. Vijayakumar, I. Hubert Joe, C. P. R. Nair, V. S. Jayakumar, Chem. Phys., 343, 83-99 (2008).M. Govindarajan, M. Karabacak, A. Suvitha, S. Periandy, Spectrochim. Acta A, 89,137-148 (2012).M. Govindarajan, M. Karabacak, A. Suvitha, S. Periandy, Spectrochim. Acta A, 89,137-148 (2012).

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