PMID: 11916389Mar 28, 2002Paper

Direct evidence for base-mediated decomposition of alkyl hydroperoxides (ROOH) in the gas phase

Journal of the American Chemical Society
Stephen J BlanksbyShuji Kato

Abstract

The reaction of F(-) with CH(3)OOH has been studied in the gas phase using a tandem flowing afterglow-selected ion flow tube apparatus. The reaction is rapid (k = 1.23 x 10(-9) cm(3) s(-1), 49% efficiency), and formation of HO(-) + CH(2)O + HF is the major reaction channel observed (85%). Isotopic labeling, reactions of F(-) with larger alkyl hydroperoxides, and computational studies demonstrate that the major product ion, HO(-), is formed via a concerted elimination mechanism that appears to be general to all alkyl hydroperoxides possessing an alpha-hydrogen. This mechanism represents a base-mediated decomposition of alkyl hydroperoxides in the gas phase that may have important implications for solution and biochemical reactions. The reverse reaction, CH(3)OO(-) + HF is also efficient (k = 2.43 x 10(-9) cm(3) s(-1)). The major product ensemble HO(-) + CH(2)O + HF (81%) is identical to that of the forward reaction, and represents a novel neutral-catalyzed decomposition of the anion.

References

Feb 26, 2000·Carcinogenesis·L J Marnett
Nov 20, 2001·Chemical Reviews·R C MurphyJ Hevko

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Citations

Jul 26, 2006·The Journal of Chemical Physics·Grigoriy VaynerWilliam L Hase
Feb 3, 2015·Critical Reviews in Biotechnology·Ruud HeshofJohanna Buchert
Jan 25, 2017·Journal of the American Chemical Society·Subha PratiharWilliam L Hase
Oct 18, 2014·Physical Chemistry Chemical Physics : PCCP·Sui SoGabriel da Silva
Jun 10, 2010·European Journal of Mass Spectrometry·Stephanie M VillanoW Carl Lineberger
Oct 16, 2010·Journal of Computational Chemistry·Jie LuoXiumei Pan
May 27, 2005·Organic & Biomolecular Chemistry·Steven M Bachrach, Andrey Pereverzev
Mar 23, 2017·Philosophical Transactions. Series A, Mathematical, Physical, and Engineering Sciences·Xinyou Ma, William L Hase
Apr 22, 2020·Annual Review of Physical Chemistry·Bhumika Jayee, William L Hase
Mar 4, 2021·Physical Chemistry Chemical Physics : PCCP·Ezequiel Fragoso Vieira LeitãoElizete Ventura
Jul 18, 2008·The Journal of Physical Chemistry. a·Jack Simons
Feb 27, 2009·The Journal of Physical Chemistry. a·Upakarasamy Lourderaj, William L Hase
Oct 16, 2009·The Journal of Physical Chemistry. a·Stephanie M VillanoW Carl Lineberger
Jul 31, 2007·Journal of the American Chemical Society·José G LópezWilliam L Hase

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