期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 87, 期 22, 页码 15530-15538出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.2c02080
关键词
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资金
- European Social Fund [2020/37/N/ST4/01562]
- National Science Center, Poland
- NCN
- [2018/31/B/ST4/02354]
- [POWR.03.02.00-00-I007/16-00]
The reaction between the stable nitroxyl radical TEMPO center dot and the 2,2'-diphenyl-1-picrylhydrazyl radical (dpph(center dot)) is greatly accelerated in the presence of resveratrol. This surprising synergistic effect is proposed to occur through a mutual activation mechanism between TEMPO center dot/RSV, resulting in extremely fast scavenging of dpph(center dot) radical.
The reaction of the 2,2'-diphenyl-1-picrylhydrazyl radical (dpph(center dot)) with resveratrol in methanol (k(MeOH) = 192 M-1 s(-1)) is greatly accelerated in the presence of stable nitroxyl radical TEMPO center dot (k(m)(ix)(MeOH) = 1.4 x 10(3) M-1 s(-1)). This synergistic effect is surprising because TEMPO center dot alone reacts with dpph(center dot) relatively slowly (k(S) = 31 M-1 s(-1) in methanol and 0.03 M-1 s(-1) in nonpolar ethyl acetate). We propose a putative mechanism in which a mutual activation occurs within the acid-base pair TEMPO center dot/RSV to the resveratrol (RSV) anion and TEMPOH center dot+ radical cation, both being extremely fast scavengers of the dpph(center dot) radical. The fast initial reaction is followed by a much slower but continuous decay of dpph(center dot) because a nitroxyl radical is recovered from the TEMPOnium cation, which is reduced directly by RSV/RSV- to TEMPO center dot or recovered indirectly via a reaction with methanol, producing TEMPOH subsequently oxidized by dpph(center dot) to TEMPO center dot.
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