Effect of solvent polarizability on the keto/enol equilibrium of selected bioactive molecules from the 1,3,4-thiadiazole group with a 2,4-hydroxyphenyl function
Authors:
- Arkadiusz Matwijczuk,
- Dariusz Karcz,
- Radosław Walkowiak,
- Justyna Furso,
- Bożena Gładyszewska,
- Sławomir Wybraniec,
- Andrzej Niewiadomy,
- Grzegorz P. Karwasz,
- Mariusz Gagoś
Abstract
Three novel 1,3,4-tiadiazole-derived compounds with biological-activity, i.e. 4-(5-(methylamino)-1,3,4-thiadiazol-2-yl)benzene-1,3-diol (MDFT), 4-(5-(phenylamino)-1,3,4-thiadiazol-2-yl)benzene-1,3-diol (PhATB), and 4-(5-(4-chlorophenylamino)-1,3,4-thiadiazol-2-yl)benzene-1,3-diol (4-CIPhATB) were characterized with the use of several spectroscopic methods. Detailed UV-Vis studies revealed keto/enol tautomerism of the examined compounds. The absorption spectra recorded in non-polar solvents exhibited bands that were characteristic of keto tautomers, while in polar solvents the enol form was predominant. A number of spectra revealed the presence of both tautomeric forms in the solution. The keto/enol equilibria observed were both solvent- and temperature-dependent. The keto/enol equilibrium was also observed using FTIR spectroscopy. A detailed analysis of the spectroscopic data leads to a conclusion that the solvent-induced tautomerism of the selected compounds from the 1,3,4-thiadiazole group does not depend on the electric dipole moment of the solvent but more likely on its average electric polarizability. Additionally, a clear effect of the substituent present in the molecule on the tautomeric equilibrium in the selected 1,3,4-thiadiazole analogues was noted. View: PDF | PDF w/ Links Related Content
- Record ID
- CUTe9d6c123aa764770aa717e829d6b6feb
- Publication categories
- ;
- Author
- Journal series
- Journal of Physical Chemistry A, ISSN 1089-5639, e-ISSN 1520-5215
- Issue year
- 2017
- Vol
- 121
- No
- 7
- Pages
- 1402-1411
- Other elements of collation
- tab.; wykr.; Bibliografia (na s.) - 1410-1411; Bibliografia (liczba pozycji) - 50; Oznaczenie streszczenia - Abstr.; Numeracja w czasopiśmie - Vol. 121, Iss. 7
- Keywords in English
- solvent polarizability, keto/enol equilibrium, 1,3,4-thiadiazole
- DOI
- DOI:10.1021/acs.jpca.6b08707 Opening in a new tab
- URL
- http://pubs.acs.org/doi/abs/10.1021/acs.jpca.6b08707 Opening in a new tab
- Language
- eng (en) English
- Score (nominal)
- 30
- Additional fields
- Indeksowana w: Web of Science, Scopus
- Uniform Resource Identifier
- https://cris.pk.edu.pl/info/article/CUTe9d6c123aa764770aa717e829d6b6feb/
- URN
urn:pkr-prod:CUTe9d6c123aa764770aa717e829d6b6feb
* presented citation count is obtained through Internet information analysis, and it is close to the number calculated by the Publish or PerishOpening in a new tab system.