Experimental and Theoretical Reduction Potentials of Some Biologically Active ortho-Carbonyl para-Quinones
Abstract
:1. Introduction
2. Materials and Methods
2.1. Cyclic Voltammetry
2.2. Computational Details
3. Results and Discussion
3.1. Cyclic Voltammetry
3.2. Theoretical First and Second One-Electron Reduction Potentials
4. Conclusions
Supplementary Materials
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Sample Availability: Samples of the compounds 1, 2, 3 and 4 are available from the authors. |
Compounds | Semiquinone | Hidroquinone Dianion | E°I | E°II | ΔEpI | ΔEpII | ||
---|---|---|---|---|---|---|---|---|
EpcIa | EpaIb | EpcIIa | EpaIIb | |||||
1 | −479 ± 2 | −410 ± 6 | −1107 ± 4 | −1044 ± 4 | −445 | −1076 | −69 | −63 |
2 | −650 ± 3 | −571 ± 5 | −1066 ± 4 | −1007 ± 2 | −611 | −1037 | −79 | −59 |
3 | −390 ± 1 | −323 ± 9 | −1022 ± 4 | −923 ± 5 | −357 | −973 | −67 | −99 |
4 | −382 ± 2 | −317 ± 5 | −1033 ± 3 | −945 ± 3 | −350 | −989 | −65 | −88 |
Compounds | ΔE°I–II (mV) | ln K |
---|---|---|
1 | 631 | 25.2 |
2 | 426 | 17.0 |
3 | 616 | 24.6 |
4 | 639 | 25.6 |
Compound | Ered | ||||
---|---|---|---|---|---|
BHandHLYP | M06 | PBE0 | E°(exp) | ||
1st RP | 1 | −644 | −497 | −583 | −445 |
2 | −901 | −725 | −697 | −611 | |
3 | −463 | −314 | −362 | −357 | |
4 | −483 | −306 | −366 | −350 | |
2nd RP | 1 | −2037 | −1769 | −1843 | −1076 |
2 | −2131 | −1842 | −1934 | −1037 | |
3 | −1950 | −1651 | −1624 | −973 | |
4 | −1954 | −1669 | −1660 | −989 |
Molecule | Q | SQ•− | HQ−2 | |||
---|---|---|---|---|---|---|
EHOMO | ELUMO | ESOMO | ELUMO | EHOMO | ELUMO | |
1 | −9.58 | −2.59 | −1.37 | 2.98 | 3.99 | 7.36 |
2 | −8.79 | −2.28 | −1.31 | 2.72 | 3.58 | 5.94 |
3 | −8.55 | −2.69 | −1.87 | 2.23 | 2.93 | 5.71 |
4 | −8.51 | −2.66 | −1.91 | 2.19 | 2.82 | 5.48 |
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Martínez-Cifuentes, M.; Salazar, R.; Ramírez-Rodríguez, O.; Weiss-López, B.; Araya-Maturana, R. Experimental and Theoretical Reduction Potentials of Some Biologically Active ortho-Carbonyl para-Quinones. Molecules 2017, 22, 577. https://doi.org/10.3390/molecules22040577
Martínez-Cifuentes M, Salazar R, Ramírez-Rodríguez O, Weiss-López B, Araya-Maturana R. Experimental and Theoretical Reduction Potentials of Some Biologically Active ortho-Carbonyl para-Quinones. Molecules. 2017; 22(4):577. https://doi.org/10.3390/molecules22040577
Chicago/Turabian StyleMartínez-Cifuentes, Maximiliano, Ricardo Salazar, Oney Ramírez-Rodríguez, Boris Weiss-López, and Ramiro Araya-Maturana. 2017. "Experimental and Theoretical Reduction Potentials of Some Biologically Active ortho-Carbonyl para-Quinones" Molecules 22, no. 4: 577. https://doi.org/10.3390/molecules22040577