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 editorsBoraei, Ahmed T.A.; Haukka, Matti; Soliman, Saied M.; Barakat, Assem

Journal or seriesJournal of Molecular Structure

ISSN0022-2860

eISSN1872-8014

Publication year2021

Volume1227

Article number129429

PublisherElsevier BV

Place of PublicationAmsterdam

Publication countryNetherlands

Publication languageEnglish

DOIhttps://doi.org/10.1016/j.molstruc.2020.129429

Publication open accessNot 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.


Keywordssynthesistautomerismsupramolecular chemistry

Free keywordstriazolyl-indole; tautomerism; Hirshfeld surface analysis; DFTNBO


Contributing organizations


Ministry reportingYes

Reporting Year2021

JUFO rating1


Last updated on 2024-03-04 at 20:46