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Synthesis, Vibrational Spectra, and DFT Simulations of 3-bromo-2-methyl-5-(4-nitrophenyl)thiophene

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Journal of Applied Spectroscopy Aims and scope

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.

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Authors and Affiliations

  1. College of Pharmacy, University of Babylon, P.O. Box 4, Babylon, Iraq

    A. A. Balakit

  2. Bozok University, Department of Physics, Faculty of Art & Sciences, 66100, Yozgat, Turkey

    Y. Sert

  3. Sorgun Vocational School, Bozok University, 66100, Yozgat, Turkey

    Y. Sert

  4. Erzincan University, Department of Physics, Faculty of Art & Sciences, 24100, Erzincan, Turkey

    Ç. Çırak

  5. School of Chemistry, Cardiff University, Main Building, Park Place, Cardiff, CF10 3AT, UK

    K. Smith & B. M. Kariuki

  6. Cornea Research Chair, Department of Optometry, College of Applied Medical Sciences, King Saud University, P.O. Box 10219, Riyadh, 11433, Saudi Arabia

    G. A. El-Hiti

Authors
  1. A. A. Balakit
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  2. Y. Sert
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  3. Ç. Çırak
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  4. K. Smith
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  5. B. M. Kariuki
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  6. G. A. El-Hiti
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Corresponding authors

Correspondence to A. A. Balakit, Y. Sert or G. A. El-Hiti.

Additional information

Abstract of article is published in Zhurnal Prikladnoi Spektroskopii, Vol. 84, No. 5, p. 834, September–October, 2017.

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Balakit, A.A., Sert, Y., Çırak, Ç. et al. Synthesis, Vibrational Spectra, and DFT Simulations of 3-bromo-2-methyl-5-(4-nitrophenyl)thiophene. J Appl Spectrosc 84, 888–899 (2017). https://doi.org/10.1007/s10812-017-0561-9

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  • DOI: https://doi.org/10.1007/s10812-017-0561-9

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