2024-03-29T00:04:18Zhttps://riubu.ubu.es/oai/requestoai:riubu.ubu.es:10259/47862022-04-29T12:02:45Zcom_10259_4363com_10259_5086com_10259_2604col_10259_4364
Structure, tautomerism, spectroscopic and DFT study of o-vanillin derived Schiff bases containing thiophene ring
Rodríguez, María R.
Plá, Julián del
Piro, Oscar Enrique
Echeverría, Gustavo A.
Espino Ordóñez, Gustavo
Pis Diez, Reinaldo
Parajón Costa, Beatriz S.
González Baró, Ana C.
Thiophene
o-vanillin
X-ray crystal structure
Tautomerism
Spectroscopy
DFT
Two Schiff bases derived from o-vanillin (o-HVA), a well-known antioxidant hydroxo aldehyde, have been obtained from condensation with 2-thiophenecarboxilic acid hydrazide (TPNNH) and 2-thiophenemethylamine (TPNH2), respectively. The inclusion of thiophene is based on its significance in the development of effective therapeutic agents. The study of the compounds oVATPNNH and oVATPNH2 includes solid state structural and spectroscopic analysis by single-crystal X-ray diffraction and vibrational spectroscopy (FTIR and Raman). The crystal structure of oVATPNH2 shows a peculiar rotational disorder in the heterocycle. Tautomeric equilibria in solution, which depends on the molecule structure and the nature of the solvent, were analysed by means of 1H and 13C{1H} NMR along with electronic spectroscopy. Tautomerism plays an important role not only in the molecular interactions but also in the behaviour of the Schiff base when acting as a ligand in coordination compounds. Results obtained from DFT calculations were used in the interpretation of the experimental data and in the spectral assignments.
2018-05-16
2018-08
2020-08
info:eu-repo/semantics/article
0022-2860
http://hdl.handle.net/10259/4786
10.1016/j.molstruc.2018.03.120
eng
Journal of Molecular Structure. 2018, V. 1165, p. 381-390
https://doi.org/10.1016/j.molstruc.2018.03.120
info:eu-repo/grantAgreement/MINECO/CTQ2014-58812-C2-1-R
info:eu-repo/grantAgreement/MINECO/CTQ2015-70371-REDT
http://creativecommons.org/licenses/by-nc-nd/4.0/
info:eu-repo/semantics/openAccess
Attribution-NonCommercial-NoDerivatives 4.0 International
Elsevier