Dihalide and pseudohalide radical anions as oxidizing agents in nonaqueous solvents

The Journal of Physical Chemistry. a
R MichalskiA Marcinek

Abstract

The dihalide and pseudohalide radical anions, strong one-electron oxidants, can be selectively generated in aqueous solutions by pulse radiolysis. Radiolysis of salts of the bulky 1-butyl-3-methylimidazolium cation with Cl(-), Br(-), SCN(-), and N(3)(-) anions allows efficient generation of the same species (Cl(2)(*-), Br(2)(*-), (SCN)(2)(*-), and N(6)(*-) radical anions) also in neat ionic liquids and in nonaqueous solvents with the addition of small amounts of the salt. The oxidative power of dichloride radical anion, lowered in the dichloromethane as compared to the aqueous solution, remains sufficient for oxidation of N,N,N',N'-tetramethyl-p-phenylenediamine (TMPD, (2)k = (2.0 +/- 0.1) x 10(9) M(-1) s(-1)), phenothiazine (PZ, (2)k = (2.1 +/- 0.1) x 10(9) M(-1) s(-1)), 10-methylphenothiazine (MPZ, (2)k = (9.3 +/- 0.1) x 10(7) M(-1) s(-1)), and 3-methylindole (scatole, SCT, (2)k = (6.8 +/- 0.1) x 10(7) M(-1) s(-1)). It diminishes on going to Br(2)(*-) (reacts only with TMPD, (2)k = (5.4 +/- 0.3) x 10(8) M(-1) s(-1), and PZ, (2)k = (4.8 +/- 0.3) x 10(8) M(-1) s(-1)) while (SCN)(2)(*-) and N(6)(*-) radical anions oxidize only TMPD, (2)k = (5.1 +/- 0.5) x 10(8) M(-1) s(-1) and (2)k approximately 10(8) M(-1) s(-1), respectively.

References


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Citations

Jan 28, 2014·Photochemistry and Photobiology·Laura A PeñaPatrick E Hoggard
Jul 4, 2013·The Journal of Physical Chemistry. a·Ilya A ShkrobJames F Wishart
Jan 17, 2015·Physical Chemistry Chemical Physics : PCCP·Sergiy V Rosokha, Alfredo Traversa
Jun 10, 2017·The Journal of Chemical Physics·Ireneusz JanikG N R Tripathi
Jun 12, 2013·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Alissa M ChanPatrick E Hoggard
Oct 12, 2010·The Journal of Physical Chemistry. a·Radosław MichalskiAndrzej Marcinek
Aug 23, 2018·The Journal of Physical Chemistry. B·V I Borovkov

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