A1 Journal article (refereed)
X-ray Single Crystal Structure, Tautomerism Aspect, DFT, NBO, and Hirshfeld Surface Analysis of a New Schiff Bases Based on 4-Amino-5-Indol-2-yl-1,2,4-Triazole-3-Thione Hybrid (2021)


Boraei, A. T. A., Soliman, S. M., Haukka, M., El Tamany, E. S. H., Al-Majid, A. M., & Barakat, A. (2021). X-ray Single Crystal Structure, Tautomerism Aspect, DFT, NBO, and Hirshfeld Surface Analysis of a New Schiff Bases Based on 4-Amino-5-Indol-2-yl-1,2,4-Triazole-3-Thione Hybrid. Crystals, 11(9), Article 1041. https://doi.org/10.3390/cryst11091041


JYU authors or editors


Publication details

All authors or editors: Boraei, Ahmed T. A.; Soliman, Saied M.; Haukka, Matti; El Tamany, El Sayed H.; Al-Majid, Abdullah Mohammed; Barakat, Assem

Journal or series: Crystals

eISSN: 2073-4352

Publication year: 2021

Publication date: 29/08/2021

Volume: 11

Issue number: 9

Article number: 1041

Publisher: MDPI AG

Publication country: Switzerland

Publication language: English

DOI: https://doi.org/10.3390/cryst11091041

Publication open access: Openly available

Publication channel open access: Open Access channel

Publication is parallel published (JYX): https://jyx.jyu.fi/handle/123456789/78249


Abstract

Four different new Schiff basses tethered indolyl-triazole-3-thione hybrid were designed and synthesized. X-ray single crystal structure, tautomerism, DFT, NBO and Hirshfeld analysis were explored. X-ray crystallographic investigations with the aid of Hirshfeld calculations were used to analyze the molecular packing of the studied systems. The H···H, H···C, S···H, Br···C, O···H, C···C and N···H interactions are the most important in the molecular packing of 3. In case of 4, the S···H, N···H, S···C and C···C contacts are the most significant. The results obtained from the DFT calculations indicated that the thione tautomer is energetically lower than the thiol one by 13.9545 and 13.7464 kcal/mol for 3 and 4, respectively. Hence, the thione tautomer is the most stable one which agree with the reported X-ray structure. In addition, DFT calculations were used to compute the electronic properties while natural bond orbital calculations were used to predict the stabilization energies due to conjugation effects. Both compounds are polar where 4 (3.348 Debye) has a higher dipole moment than 3 (2.430 Debye).


Keywords: nitrogen compounds; chemical synthesis; tautomerism

Free keywords: Schiff bases; indolyl-triazole-3-thione; tautomerism aspect; Hirshfeld Surface Analysis


Contributing organizations


Ministry reporting: Yes

Reporting Year: 2021

JUFO rating: 1


Last updated on 2022-20-09 at 14:42