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

Reporting Year: 2021

JUFO rating: 1