Reaction of 2,2-Diphenyl-1-picrylhydrazyl with HO•, O2•–, HO– ,and HOO– Radicals and Anions
Abstract
:1. Introduction
2. Results and discussion
2.1. Reaction with potassium superoxide in the presence of crown ether 18C6
Time (min) | Unreacted DPPH (%) |
---|---|
5 | 95.66 |
25 | 93.59 |
45 | 91.94 |
65 | 90.70 |
90 | 87.40 |
120 | 83.05 |
1440 (24h) | 71.90 |
Reaction c | DPPH-H b 2a | O2N-DPPH-Hb 2b | Ph2NHa 4 | Ph2N-NPh2a 6 | HO-DPPH-H b 7 | Betaineb 8 | ||||||
Rf | % | Rf | % | Rf | % | Rf | % | Rf | % | Rf | % | |
A (HO–) | 0.67 | 46 | – | – | 0.44 | 22 | 0.68 | 1 | 0.59 | 8 | 0.04 | 6 |
B (HO•) | 0.68 | 20 | 0.31 | 12 | 0.44 | 25 | – | – | 0.57 | 11 | 0.04 | 9 |
C (O2•–) | 0.67 | 65 | 0.30 | 12 | 0.43 | 4 | 0.67 | 0.4 | – | – | – | – |
D (HOO–) | 0.67 | 70 | 0.29 | 10 | 0.44 | 3 | – | – | – | – | 0.03 | 5 |
2.2. Reaction of DPPH with the hydroxide anion and the hydroxy free radical
- (i)
- As shown in Table 2, in the photochemical reaction, in addition to compounds 2b, 7, and 8, diphenylamine (4) was also identified and determined quantitatively.
- (ii)
- From the reaction with solid potassium hydroxide the same four products were detected qualitatively.
- (iii)
- The reaction with benzyltrimethylammonium hydroxide afforded 2b, 6, 7, and tetraphenylhydrazine (4).
2.3. Reaction of DPPH with the hydrogen peroxide anion
2.4. Comparison between reactions of DPPH with O2•–, HO•, HO–, and HOO–
3. Conclusions
4. Experimental part
Reactions of 2,2-diphenyl-1-picrylhydrazyl, DPPH (1a) with KO2, KOH, benzyltrimethylammonium hydroxide, FotoFentonTM2, and H2O2 at room temperature.
Kinetics of the reaction between DPPH (1a) and potassium superoxide.
Reaction of the supramolecular complex [18C6…K]+DPPH− with potassium superoxide.
NMR Identification of reaction products mono-nitro-DPPH-H (2b), diphenylamine (4), and tetraphenylhydrazine (6).
Acknowledgements
References
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Hristeac, E.N.; Caproiu, M.T.; Pencu, G.; Hillebrand, M.; Constantinescu, T.; Balaban, A.T. Reaction of 2,2-Diphenyl-1-picrylhydrazyl with HO•, O2•–, HO– ,and HOO– Radicals and Anions. Int. J. Mol. Sci. 2006, 7, 130-143. https://doi.org/10.3390/i7050130
Hristeac EN, Caproiu MT, Pencu G, Hillebrand M, Constantinescu T, Balaban AT. Reaction of 2,2-Diphenyl-1-picrylhydrazyl with HO•, O2•–, HO– ,and HOO– Radicals and Anions. International Journal of Molecular Sciences. 2006; 7(5):130-143. https://doi.org/10.3390/i7050130
Chicago/Turabian StyleHristeac, Elena N., Miron T. Caproiu, Gabriela Pencu, Mihaela Hillebrand, Titus Constantinescu, and Alexandru T. Balaban. 2006. "Reaction of 2,2-Diphenyl-1-picrylhydrazyl with HO•, O2•–, HO– ,and HOO– Radicals and Anions" International Journal of Molecular Sciences 7, no. 5: 130-143. https://doi.org/10.3390/i7050130