A1 Alkuperäisartikkeli tieteellisessä aikakauslehdessä
Synthesis of Enaminones-Based Benzo[d]imidazole Scaffold : Characterization and Molecular Insight Structure (2020)

Alshahrani, S., Soliman, S. M., Alamary, A. S., Al-Majid, A. M., Haukka, M., Yousuf, S., & Barakat, A. (2020). Synthesis of Enaminones-Based Benzo[d]imidazole Scaffold : Characterization and Molecular Insight Structure. Crystals, 10(10), Article 955. https://doi.org/10.3390/cryst10100955

JYU-tekijät tai -toimittajat

Julkaisun tiedot

Julkaisun kaikki tekijät tai toimittajat: Alshahrani, Saeed; Soliman, Saied M.; Alamary, Abdullah Saleh; Al-Majid, Abdullah Mohammed; Haukka, Matti; Yousuf, Sammer; Barakat, Assem

Lehti tai sarja: Crystals

eISSN: 2073-4352

Julkaisuvuosi: 2020

Ilmestymispäivä: 21.10.2020

Volyymi: 10

Lehden numero: 10

Artikkelinumero: 955

Kustantaja: MDPI AG

Julkaisumaa: Sveitsi

Julkaisun kieli: englanti

DOI: https://doi.org/10.3390/cryst10100955

Julkaisun avoin saatavuus: Avoimesti saatavilla

Julkaisukanavan avoin saatavuus: Kokonaan avoin julkaisukanava

Julkaisu on rinnakkaistallennettu (JYX): https://jyx.jyu.fi/handle/123456789/72472

Tiivistelmä

(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. Reaction of enaminone derivative 1 with acetylacetone in the presence of AcOH/NH4OAc under reflux afforded the cyclized pyridino-benzo[d]imidazole derivative 3. The latter compound was converted into the corresponding β-enaminone 4 with DMF-DMA. The single crystal X-ray diffraction technique eventually confirmed the assigned chemical structure of the N-alkyl-β-enaminone 2 and pyridino-benzo[d]imidazole derivative 3. N-alkyl-β-enaminone 2 crystallized in the monoclinic space group P21/n with unit cell parameters of a = 9.8953(3) Å, b = 5.7545(2) Å, c = 21.7891(7) Å, and β =100.627(2)°, and with one molecule per asymmetric unit. On the other hand, compound 3 crystallized in the orthorhombic crystal system and space group P212121 with unit cell parameters of a = 6.82950(10) Å, b = 8.00540(10) Å, c = 22.4779(2) Å, and also with one molecule per asymmetric unit. Based on Hirshfeld analysis, the H...H (51.3%), O...H (10.0%), N...H (10.3%), and C...H (27.6%) contacts in 2 and the H...H (46.8%), O...H (9.9%), N...H (13.0%), and C...H (21.6%) in addition to the C…C (6.7%) interactions in 3 are the most important towards crystal stability via molecular packing. The main difference is the presence of π–π interaction among the molecular units of 3 but not in 2. The calculated 1H and 13C NMR chemical shifts showed good agreements with experimental data. Electronic properties and reactivity parameters of both compounds are also calculated and compared.

YSO-asiasanat: kemiallinen synteesi; orgaaniset yhdisteet; kiteet; tiheysfunktionaaliteoria

Vapaat asiasanat:  benzo[d]imidazole; β-enaminone; DMF-DMA; Hirshfeld analysis; DFT

Liittyvät organisaatiot

OKM-raportointi: Kyllä

Raportointivuosi: 2020

JUFO-taso: 1