Palladium(0) Catalyzed Synthesis of (E)-4-Bromo-N-((3-bromothiophen-2-yl)methylene)-2-methylaniline Derivatives via Suzuki Cross-Coupling Reaction: An Exploration of Their Non-Linear Optical Properties, Reactivity and Structural Features
Abstract
:1. Introduction
2. Results and Discussion
2.1. Chemistry
2.2. Density Functional Theory (DFT) Studies
2.2.1. Frontier Molecular Orbital (FMO) Studies
2.2.2. Nonlinear Optical Properties
2.2.3. Molecular Electrostatic Potential
2.2.4. Conceptual DFT Reactivity Descriptors
3. Materials and Methods
3.1. General
3.2. Generalized Methodology for the Synthesis of 3a and 3b
3.3. Generalized Methodology for the Suzuki Coupling of 3a and 3b
3.4. Characterization Data
3.5. Computational Methods
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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Compound | EHOMO | ELUMO | HOMO-LUMO Gap | Hyperpolarizability |
---|---|---|---|---|
5a | −5.95 | −2.01 | 3.94 | 4218.78 |
5b | −5.75 | −2.00 | 3.76 | 9932.64 |
5c | −6.23 | −2.08 | 4.15 | 1460.58 |
5d | −5.88 | −2.16 | 3.72 | 7588.64 |
6a | −6.09 | −2.09 | 4.00 | 2709.57 |
6b | −5.81 | −1.84 | 3.97 | 2751.87 |
6c | −5.98 | −2.03 | 3.95 | 3232.40 |
6d | −5.96 | −2.02 | 3.94 | 3605.95 |
Compounds | Ionization Potential, I (eV) | Electron Affinity, A (eV) | Chemical Hardness, ƞ (eV) | Electronic Chemical Potential, μ (eV) | Electrophilicity Index, ω (eV) |
---|---|---|---|---|---|
5a | 5.95 | 2.01 | −1.97 | 3.98 | −4.03 |
5b | 5.75 | 2.00 | −1.88 | 3.87 | −4.00 |
5c | 6.23 | 2.08 | −2.07 | 4.16 | −4.16 |
5d | 5.88 | 2.16 | −1.86 | 4.02 | −4.35 |
6a | 6.09 | 2.09 | −2.00 | 4.09 | −4.18 |
6b | 5.81 | 1.84 | −1.99 | 3.82 | −3.68 |
6c | 5.98 | 2.03 | −1.98 | 4.01 | −4.06 |
6d | 5.96 | 2.02 | −1.97 | 3.99 | −4.04 |
Sample Availability: Samples of the compounds are not available from the authors. |
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Rizwan, K.; Rasool, N.; Hashmi, M.A.; Noreen, S.; Zubair, M.; Arshad, M.; Shah, S.A.A. Palladium(0) Catalyzed Synthesis of (E)-4-Bromo-N-((3-bromothiophen-2-yl)methylene)-2-methylaniline Derivatives via Suzuki Cross-Coupling Reaction: An Exploration of Their Non-Linear Optical Properties, Reactivity and Structural Features. Molecules 2021, 26, 5605. https://doi.org/10.3390/molecules26185605
Rizwan K, Rasool N, Hashmi MA, Noreen S, Zubair M, Arshad M, Shah SAA. Palladium(0) Catalyzed Synthesis of (E)-4-Bromo-N-((3-bromothiophen-2-yl)methylene)-2-methylaniline Derivatives via Suzuki Cross-Coupling Reaction: An Exploration of Their Non-Linear Optical Properties, Reactivity and Structural Features. Molecules. 2021; 26(18):5605. https://doi.org/10.3390/molecules26185605
Chicago/Turabian StyleRizwan, Komal, Nasir Rasool, Muhammad Ali Hashmi, Sadia Noreen, Muhammad Zubair, Mahwish Arshad, and Syed Adnan Ali Shah. 2021. "Palladium(0) Catalyzed Synthesis of (E)-4-Bromo-N-((3-bromothiophen-2-yl)methylene)-2-methylaniline Derivatives via Suzuki Cross-Coupling Reaction: An Exploration of Their Non-Linear Optical Properties, Reactivity and Structural Features" Molecules 26, no. 18: 5605. https://doi.org/10.3390/molecules26185605