Science and Technology Production
Article
Authorship
Cardona López, Jessica
;
LEZAMA, JOSÉ OSVALDO GUY
;
Bonesi, Sergio Mauricio
;
Robles, Norma Lis
Date
2025
Publishing House and Editing Place
ELSEVIER SCIENCE BV
Magazine
JOURNAL OF MOLECULAR STRUCTURE,
vol. 1322
ELSEVIER SCIENCE BV
Summary
Information provided by the agent in
SIGEVA
This investigation deals with an alternative thionation synthetic strategy for the preparation of N-(4-fluorophenyl)furan-2-carbothioamide using elemental sulphur and applying the Willgerodt-Kindler reaction. The carbothioamide was obtained with ca 30 % yield assessing the purity (higher than 90 %) with GC/MS spectrometry, and the compound was fully characterised by NMR (1H, 13C), FTIR and UV–visible spectroscopies. Indeed, 1H NMR spectroscopic analysis demonstrated that a single conforme...
This investigation deals with an alternative thionation synthetic strategy for the preparation of N-(4-fluorophenyl)furan-2-carbothioamide using elemental sulphur and applying the Willgerodt-Kindler reaction. The carbothioamide was obtained with ca 30 % yield assessing the purity (higher than 90 %) with GC/MS spectrometry, and the compound was fully characterised by NMR (1H, 13C), FTIR and UV–visible spectroscopies. Indeed, 1H NMR spectroscopic analysis demonstrated that a single conformer with anti-anti geometry was formed attributed to the observation of only one N-H signal (9.37 ppm) of the NH-C=S group and, FTIR spectroscopy (NH stretching at 3372 cm−1) also reinforces this observation. UV-visible absorption and fluorescence emission spectra were recorded in different polar and nonpolar solvents (acetonitrile, ethanol and n-heptane) and the λ0,0 cross point displays a bathochromic shift of 11 nm with the increasing solvent polarity. The fluorescence quantum yield (ϕf) has been measured at room temperature concluding that this carbothioamide derivative is not a fluorescent compound showing a ϕf value of 0.0002. Finally, theoretical calculations have been carried out to estimate the NMR chemical shifts as well as vibrational frequencies values of the anti-anti isomer and these values were compared with the experimental data obtaining satisfactorily correlations.
Show more
Show less
Key Words
ECO-FRIENDLY SYNTHETIC METHODOLOGYCARBOTHIOAMIDESQUANTUM CHEMICAL CALCULATIONSSPECTROSCOPY CHARACTERIZATIONS