Synthesis and X-ray Crystal Structure of New Substituted 3-4′-Bipyrazole Derivatives : Hirshfeld Analysis, DFT and NBO Studies
Boraei, A. T. A., Haukka, M., Sarhan, A. A. M., Soliman, S. M., Al-Majid, A. M., & Barakat, A. (2021). Synthesis and X-ray Crystal Structure of New Substituted 3-4′-Bipyrazole Derivatives : Hirshfeld Analysis, DFT and NBO Studies. Crystals, 11(8), Article 953. https://doi.org/10.3390/cryst11080953
DisciplineEpäorgaaninen ja analyyttinen kemiaEpäorgaaninen kemiaInorganic and Analytical ChemistryInorganic Chemistry
© 2021 by the authors. Licensee MDPI, Basel, Switzerland.
A new compounds named 3-4′-bipyrazoles 2 and 3 were synthesized in high chemical yield from a reaction of pyran-2,4-diketone 1 with aryl hydrazines under thermal conditions in MeOH. Compound 2 was unambiguously confirmed by single-crystal X-ray analysis. It crystalizes in a triclinic crystal system and space group P-1. Its crystal structure was found to be in good agreement with the spectral characterizations. With the aid of Hirshfeld calculations, the H…H (54.8–55.3%) and H…C (28.3–29.2%) intermolecular contacts are the most dominant, while the O…H (5.8–6.5%), N…H (3.8–4.6%) and C…C (3.0–4.9%) are less dominant. The compound has a polar nature with a net dipole moment of 6.388 Debye. The BD(2)C31-C32→BD*(2)N4-C34 (27.10 kcal/mol), LP(1)N5→BD*(2)C31-C32 (36.90 kcal/mol), BD(1)C32-C34→BD*(1)C18-C31 (6.78 kcal/mol) and LP(1)N4→BD*(1)N5-C31 (7.25 kcal/mol) are the strongest π→π*, n→π*, σ-σ* and n→σ* intramolecular charge transfer processes, respectively.
Publication in research information system
MetadataShow full item record
Additional information about fundingThe authors would like to extend their sincere appreciation to the Researchers Supporting Project (RSP-2021/64), King Saud University, Riyadh, Saudi Arabia.
Showing items with similar title or keywords.
Synthesis, X-ray Structure, Conformational Analysis, and DFT Studies of a Giant s-Triazine bis-Schiff Base Almarhoon, Zainab M.; Al-Zaben, Maha I.; Ben Bacha, Abir; Haukka, Matti; El-Faham, Ayman; Soliman, Saied M. (MDPI AG, 2021)The current work involves the synthesis of 2,2′-(6-(piperidin-1-yl)-1,3,5-triazine-2,4-diyl)bis(hydrazin-2-yl-1-ylidene))bis(methanylylidene))diphenol 4, characterization, and the DFT studies of the reported compound. The ...
Synthesis of Enaminones-Based Benzo[d]imidazole Scaffold : Characterization and Molecular Insight Structure Alshahrani, Saeed; Soliman, Saied M.; Alamary, Abdullah Saleh; Al-Majid, Abdullah Mohammed; Haukka, Matti; Yousuf, Sammer; Barakat, Assem (MDPI AG, 2020)(E)-1-(1H-Benzo[d]imidazol-2-yl)-3-(dimethylamino)prop-2-en-1-one 2 was synthesized by one-pot synthesis protocol of 2-acetyl benzo[d]imidazole with dimethylformamide dimethylacetal (DMF-DMA) in xylene at 140 °C for 8 h. ...
Efficient Consecutive Synthesis of Ethyl-2-(4-Aminophenoxy) Acetate, a Precursor for Dual GK and PPARγ Activators, X-ray Structure, Hirshfeld Analysis, and DFT Studies Altowyan, Mezna Saleh; Soliman, Saied M.; Ismail, Magda M. F.; Haukka, Matti; Barakat, Assem; Ayoup, Mohammed Salah (MDPI AG, 2022)Herein, we report a facile synthesis of ethyl-2-(4-aminophenoxy)acetate 4 as a building synthon for novel dual hypoglycemic agents. This building template was synthesized by alkylation of 4-nitrophenol with ethyl bromo-acetate ...
N-(2,3,5,6-Tetrafluoropyridyl)sulfoximines : synthesis, X-ray crystallography, and halogen bonding Schumacher, Christian; Fergen, Hannah; Puttreddy, Rakesh; Truong, Khai-Nghi; Rinesch, Torsten; Rissanen, Kari; Bolm, Carsten (Royal Society of Chemistry, 2020)In the presence of KOH, NH-sulfoximines react with pentafluoropyridine to give N-(tetrafluoropyridyl)sulfoximines (NTFP-sulfoximines) in moderate to excellent yields. Either a solution-based or a superior solvent-free ...
Synthesis of Unexpected Dimethyl 2-(4-Chlorophenyl)-2,3-dihydropyrrolo[2,1-a]isoquinoline-1,3-dicarboxylate via Hydrolysis/Cycloaddition/Elimination Cascades : Single Crystal X-ray and Chemical Structure Insights Altowyan, Mezna Saleh; Soliman, Saied M.; Haukka, Matti; Al-Shaalan, Nora H.; Alkharboush, Aminah A.; Barakat, Assem (MDPI AG, 2022)Hydrolysis/[3 + 2] cycloaddition/elimination cascades employed for the synthesis of unexpected tricyclic compound derived from isoquinoline. Reaction of ethylene derivative 1 with the isoquinoline ester iminium ion 2 in ...