Synthesis, characterization and computational studies of 1,3-bis[(
E)-furan-2-yl)methylene]urea and 1,3-bis[(
E)-furan-2-yl)methylene]thiourea

Kazeem Adelani Alabi; Ibrahim Olasegun Abdulsalami; Moriam Dasola Adeoye; Shukurat Modupe Aderinto; Rasheed Adewale Adigun

doi:10.1515/psr-2019-0134

Article

Synthesis, characterization and computational studies of 1,3-bis[( E)-furan-2-yl)methylene]urea and 1,3-bis[( E)-furan-2-yl)methylene]thiourea

Kazeem Adelani Alabi , Ibrahim Olasegun Abdulsalami , Moriam Dasola Adeoye , Shukurat Modupe Aderinto and Rasheed Adewale Adigun

Published/Copyright: November 5, 2020

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From the journal Physical Sciences Reviews Volume 7 Issue 8

Abstract

Urea and thiourea derivatives: 1,3-bis[(E)-furan-2-yl)methylene]urea (BFMU) and 1,3-bis[(E)-furan-2-yl)methylene]thiourea (BFMT) were synthesized and characterized by spectrometry analyses (UV, IR, ¹H NMR and ¹³C NMR). They were screened for antibacterial (Salmonella typhi, Staphylococcus aureus, Pseudomonas aeruginosa, Xanthomonas axonopodis and Streptococcus bovis) and antifungal (Fusarium oxysporum, Colletotrichum gloeosporioides and Cercospora zeae-maydis) activities. Quantum chemical calculations of frontier molecular orbital energies (E_HOMO and E_LUMO), and their associated global parameters were carried out by DFT levels of theory, with complete relaxation in the potential energy surface using 6-31G* basis set (DFT/B3LYP/6-31G*). Azomethine functional groups (C=N) appeared at δ 7.6 ppm and δ 7.0 ppm in the proton spectra, the peaks between δ 105 and δ 160 ppm of ¹³C spectra represent the methylene carbons (C=C). BFMU is a better inhibitor of P. aeruginosa and S. bovis, while BFMT is a better inhibitor of S. typhi, S. aureus and X. axonopodis and the fungi isolates (F. oxysporum, C. gloeosporioides and C. zeae-maydis) used. The global parameters agreed favorably with the experimental results, indicating the higher activity of BFMT.

Keywords: 1,3-bis[(E)-furan-2-yl)methylene]thiourea; 1,3-bis[(E)-furan-2-yl)methylene]urea; furfural and NMR spectra

Corresponding author: Kazeem Adelani Alabi, Ph.D, Department of Chemical Sciences, Organic Synthesis and Natural Product Group, Fountain University, Osogbo, Nigeria. E-mail: qasimade@gmail.com

Author contribution: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.
Research funding: None declared.
Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

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Published Online: 2020-11-05

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https://doi.org/10.1515/psr-2019-0134

Keywords for this article

1,3-bis[(E)-furan-2-yl)methylene]thiourea; 1,3-bis[(E)-furan-2-yl)methylene]urea; furfural and NMR spectra