A1 Journal article (refereed)
Synthesis, X-Ray Structure, Tautomerism Aspect, and Chemical Insight of The 3-(1H-Indol-2-yl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-6-ol (2021)
Boraei, A. T., Haukka, M., Soliman, S. M., & Barakat, A. (2021). Synthesis, X-Ray Structure, Tautomerism Aspect, and Chemical Insight of The 3-(1H-Indol-2-yl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-6-ol. Journal of Molecular Structure, 1227, Article 129429. https://doi.org/10.1016/j.molstruc.2020.129429
JYU authors or editors
Publication details
All authors or editors: Boraei, Ahmed T.A.; Haukka, Matti; Soliman, Saied M.; Barakat, Assem
Journal or series: Journal of Molecular Structure
ISSN: 0022-2860
eISSN: 1872-8014
Publication year: 2021
Volume: 1227
Article number: 129429
Publisher: Elsevier BV
Place of Publication: Amsterdam
Publication country: Netherlands
Publication language: English
DOI: https://doi.org/10.1016/j.molstruc.2020.129429
Publication open access: Not open
Publication channel open access:
Publication is parallel published (JYX): https://jyx.jyu.fi/handle/123456789/73782
Abstract
The 3-(1H-indol-2-yl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-6-ol 2 was obtained exclusively in the enol configuration starting from triazolyl-indole derivative 1 and alkyl halo-esters in the presence of K2CO3. Chemical structure elucidations with the aid of physicochemical characterizations were used to predict its molecular structure while single crystal X-ray diffraction technique was used to shed the light on the supramolecular structure of 2. DFT calculations agreed very well with the reported X-ray structure where the most stable form thermodynamically is the enol form. Its optimized geometry agreed very well with the experimental structure where the correlation coefficients between the calculated and experimental geometric parameters are very close to 1. Using Hirshfeld analysis, the most significant intermolecular contacts are the N…H, H…C(π), O…H, S…H and C…C contacts.
Keywords: synthesis; tautomerism; supramolecular chemistry
Free keywords: triazolyl-indole; tautomerism; Hirshfeld surface analysis; DFTNBO
Contributing organizations
Ministry reporting: Yes
VIRTA submission year: 2021
JUFO rating: 1