Synthesis of Enaminones-Based Benzo[d]imidazole Scaffold: Characterization and Molecular Insight Structure
Abstract
:1. Introduction
2. Materials and Methods
- General:
2.1. (E)-1-(1H-Benzo[d]imidazol-2-yl)-3-(dimethylamino)prop-2-en-1-one 1
2.2. (E)-3-(Dimethylamino)-1-(1-methyl-1H-benzo[d]imidazol-2-yl)prop-2-en-1-one 2
2.3. 1-(6-(1H-Benzo[d]imidazol-2-yl)-2-methylpyridin-3-yl)ethan-1-one 3
2.4. (E)-1-(6-(1H-benzo[d]imidazol-2-yl)-2-methylpyridin-3-yl)-3-(dimethylamino)prop-2-en-1-one 4
3. Results and Discussion
3.1. Synthesis of β-enaminones
3.2. X-ray Structure
3.3. Hirshfeld Analysis
3.4. DFT Studies
3.5. Reactivity Studies
3.6. NMR Spectra
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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Compound | 2 | 3 |
---|---|---|
CCDC code | 1999582 | 2032100 |
Empirical formula | C13H15N3O | C15H13N3O |
Formula weight | 229.28 | 251.28 |
Temperature/K | 104(2) | 120(2) |
Radiation | CuKα (λ = 1.54178) | CuKα (λ = 1.54178) |
Crystal system | monoclinic | Orthorhombic |
Space group | P21/n | P212121 |
a/Å | 9.8953(3) | 6.82950(10) |
b/Å | 5.7545(2) | 8.00540(10) |
c/Å | 21.7891(7) | 22.4779(2) |
β/° | 100.627(2) | |
Volume/Å3 | 1219.45(7) | 1228.93(3) |
Z | 4 | 4 |
Crystal size/mm3 | 0.170 × 0.140 × 0.080 | 0.271 × 0.203 × 0.089 |
ρcalcg/cm3 | 1.249 | 1.358 |
μ/mm−1 | 0.657 | 0.710 |
F(000) | 488 | 528 |
2Θ range for data collection/° | 4.13 to 68.20 | 3.933 to 77.074. |
Index ranges | −11 ≤ h ≤ 11, −6 ≤ k ≤ 6, −25 ≤ l ≤ 26 | −8 ≤ h ≤ 8, −10 ≤ k ≤ 10, −28 ≤ l ≤ 28 |
Reflections collected | 8164 | 29119 |
Goodness-of-fit on F2 | 1.057 | 1.072 |
Data/restraints/parameters | 2209/0/157 | 2597/0/178 |
Independent reflections | 2209 [Rint = 0.0334] | 2597 [Rint = 0.0313] |
Final R indexes [all data] | R1 = 0.0555, wR2 = 0.1352 | R1 = 0.0283, wR2 = 0.0742 |
Final R indexes [I ≥ 2σ (I)] | R1 = 0.0464, wR2 = 0.1268 | R1 = 0.0288, wR2 = 0.0747 |
Largest diff. peak/hole/e Å−3 | 0.18/–0.20 | 0.137/–0.217 |
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Alshahrani, S.; Soliman, S.M.; Alamary, A.S.; Al-Majid, A.M.; Haukka, M.; Yousuf, S.; Barakat, A. Synthesis of Enaminones-Based Benzo[d]imidazole Scaffold: Characterization and Molecular Insight Structure. Crystals 2020, 10, 955. https://doi.org/10.3390/cryst10100955
Alshahrani S, Soliman SM, Alamary AS, Al-Majid AM, Haukka M, Yousuf S, Barakat A. Synthesis of Enaminones-Based Benzo[d]imidazole Scaffold: Characterization and Molecular Insight Structure. Crystals. 2020; 10(10):955. https://doi.org/10.3390/cryst10100955
Chicago/Turabian StyleAlshahrani, Saeed, Saied M. Soliman, Abdullah Saleh Alamary, Abdullah Mohammed Al-Majid, Matti Haukka, Sammer Yousuf, and Assem Barakat. 2020. "Synthesis of Enaminones-Based Benzo[d]imidazole Scaffold: Characterization and Molecular Insight Structure" Crystals 10, no. 10: 955. https://doi.org/10.3390/cryst10100955