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
| Autor: | Matti Haukka, Saied M. Soliman, Abdullah Mohammed Al-Majid, El Sayed H. El Tamany, Assem Barakat, Ahmed T. A. Boraei |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2021 |
| Předmět: |
General Chemical Engineering
tautomerism aspect Inorganic Chemistry symbols.namesake General Materials Science typpiyhdisteet Debye chemistry.chemical_classification kemiallinen synteesi Crystallography X-ray Condensed Matter Physics indolyl-triazole-3-thione Tautomer Schiff bases Hirshfeld Surface Analysis Dipole chemistry QD901-999 Thiol symbols 1 2 4 triazole 3 thione Single crystal tautomeria Natural bond orbital |
| Zdroj: | Crystals; Volume 11; Issue 9; Pages: 1041 Crystals, Vol 11, Iss 1041, p 1041 (2021) |
| ISSN: | 2073-4352 |
| DOI: | 10.3390/cryst11091041 |
| Popis: | 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). |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|