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

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...

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Bibliographic Details
Published in:Journal of applied spectroscopy 2017-11, Vol.84 (5), p.888-899
Main Authors: Balakit, A. A., Sert, Y., Çırak, Ç., Smith, K., Kariuki, B. M., El-Hiti, G. A.
Format: Article
Language:English
Subjects:
Analytical Chemistry
Atomic/Molecular Structure and Spectra
Chemical synthesis
Coupling (molecular)
Crystal structure
FOURIER TRANSFORM SPECTROMETERS
Fourier transforms
HARTREE-FOCK METHOD
HYDROFLUORIC ACID
Infrared radiation
INFRARED SPECTRA
Infrared spectroscopy
INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY
Ionization potentials
Mass spectrometry
MASS SPECTROSCOPY
Mathematical analysis
MOLECULAR ORBITAL METHOD
Molecular orbitals
NMR
NUCLEAR MAGNETIC RESONANCE
Physics
Physics and Astronomy
RAMAN SPECTRA
Raman spectroscopy
Thiophene
Vibrational spectra
X RADIATION
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Summary: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.
ISSN:0021-9037
1573-8647
DOI:10.1007/s10812-017-0561-9