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A tri(potassium sulfonate) derivative of perchlorotriphenylmethyl radical (PTM) as a stable water soluble radical-scavenger of the hydroxyl radical more powerful than 5,5-dimethyl-1-pyrroline-N-oxide†
Juan Antonio Mesa,Sergei Chávez,Lluís Fajarí,Josep Lluís Torres,Luis Juliá
RSC Advances Pub Date : 04/18/2013 00:00:00 , DOI:10.1039/C3RA41499J
Abstract

The tripotassium salt of tris(2,3,5,6-tetrachloro-4-hydroxysulfonylphenyl)methyl radical (3 K+ TSPTM3−) reacts in water with hydroxyl radical very fast with a rate constant (k = 2.4 × 1011 M−1 s−1) much higher than that of the reaction of hydroxyl radical with the spin trap 5,5-dimethyl-1-pyrroline-N-oxide (DMPO) (k = 3.4 × 109 M−1 s−1). The reaction affects the radical character of the molecule and is monitored by electron paramagnetic resonance (EPR). The hydroxyl radical scavenging is established by the characterization of the resulting water-soluble product as the dipotassium salt of 4-[bis(2,3,5,6-tetrachloro-4-hydroxysulfonylphenyl)methylene]-2,3,5,6-tetrachlorocyclohexa-2,5-dien-1-one (2).

Graphical abstract: A tri(potassium sulfonate) derivative of perchlorotriphenylmethyl radical (PTM) as a stable water soluble radical-scavenger of the hydroxyl radical more powerful than 5,5-dimethyl-1-pyrroline-N-oxide
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