Synthesis, vibrational spectra, and DFT simulations of 3-bromo-2-methyl-5-(4-nitrophenyl)thiophene

Balakit, A. A., Sert, Y., Çırak, Ç., Smith, Keith, Kariuki, Benson ORCID: https://orcid.org/0000-0002-8658-3897 and El-Hiti, G. A. 2017. Synthesis, vibrational spectra, and DFT simulations of 3-bromo-2-methyl-5-(4-nitrophenyl)thiophene. Journal of Applied Spectroscopy 84 (5) , pp. 888-899. 10.1007/s10812-017-0561-9

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Abstract

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.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Chemistry
Publisher:	Springer
ISSN:	0021-9037
Date of First Compliant Deposit:	22 November 2017
Date of Acceptance:	16 November 2017
Last Modified:	27 Nov 2024 01:30
URI:	https://orca.cardiff.ac.uk/id/eprint/106933

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