A computational and experimental re-examination of the reaction of the benzyloxyl radical with DMSO

Berlett, 1997, Protein oxidation in aging, disease, and oxidative stress, J. Biol. Chem., 272, 20313, 10.1074/jbc.272.33.20313 Davies, 1987, Protein damage and degradation by oxygen radicals. I. General aspects, J. Biol. Chem., 262, 9895, 10.1016/S0021-9258(18)48018-0 Praticò, 2008, Oxidative stress hypothesis in Alzheimer’s disease: a reappraisal, Trends Pharmacol. Sci., 29, 609, 10.1016/j.tips.2008.09.001 Chatgilialoglu, 2009, A reevaluation of the ambident reactivity of the guanine moiety towards hydroxyl radicals, Angew. Chem. Int. Ed., 48, 2214, 10.1002/anie.200805372 Lucarini, 1999, Bond dissociation energies of the N-H Bond and rate constants for the reaction with alkyl, alkoxyl, and peroxyl radicals of phenothiazines and related compounds, J. Am. Chem. Soc., 121, 11546, 10.1021/ja992904u Litwinienko, 2007, Solvent effects on the rates and mechanisms of reaction of phenols with free radicals, Acc. Chem. Res., 40, 222, 10.1021/ar0682029 Koner, 2007, Kinetic solvent effects on hydrogen abstraction reactions, Org. Lett., 9, 2899, 10.1021/ol071165g Aliaga, 2005, Solvent effects on hydrogen abstraction reactions from lactones with antioxidant properties, Org. Lett., 7, 3665, 10.1021/ol050839p Snelgrove, 2001, Kinetic solvent effects on hydrogen-atom abstractions: reliable, quantitative predictions via a single empirical equation, J. Am. Chem. Soc., 123, 469, 10.1021/ja002301e Salamone, 2013, Reactions of the cumyloxyl and benzyloxyl radicals with tertiary amides. Hydrogen abstraction selectivity and the role of specific substrate-radical hydrogen bonding, J. Org. Chem., 78, 5909, 10.1021/jo400535u Salamone, 2012, Reactions of the cumyloxyl and benzyloxyl radicals with strong hydrogen bond acceptors. Large enhancements in hydrogen abstraction reactivity determined by substrate/radical hydrogen bonding, J. Org. Chem., 77, 10479, 10.1021/jo3019889 Salamone, 2011, Hydrogen atom abstraction selectivity in the reactions of alkylamines with the benzyloxyl and cumyloxyl radicals. The importance of structure and of substrate radical hydrogen bonding, J. Am. Chem. Soc., 133, 16625, 10.1021/ja206890y Salamone, 2011, Hydrogen atom abstraction reactions from tertiary amines by benzyloxyl and cumyloxyl radicals: influence of structure on the rate-determining formation of a hydrogen-bonded prereaction complex, J. Org. Chem., 76, 6264, 10.1021/jo201025j Salamone, 2011, Diffusion controlled hydrogen atom abstraction from tertiary amines by the benzyloxyl radical. The importance of C−H/N hydrogen bonding, Org. Lett., 13, 260, 10.1021/ol102690u Pratt, 2004, Bond strengths of toluenes, anilines, and phenols: to Hammett or not, Acc. Chem. Res., 37, 334, 10.1021/ar010010k Johnson, 2009, Radicals as hydrogen bond donors and acceptors, Interdiscip. Sci. Comput. Life Sci., 1, 133, 10.1007/s12539-009-0024-3 Shukla, 2013, Chain-amplified photochemical fragmentation of N-alkoxypyridinium salts: proposed reaction of alkoxyl radicals with pyridine bases to give pyridinyl radicals, J. Org. Chem., 78, 1955, 10.1021/jo301975j Montgomery, 2000, A complete basis set model chemistry. VII. Use of the minimum population localization method, J. Chem. Phys., 112, 6532, 10.1063/1.481224 M.J. Frisch, W.G. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, et al., Gaussian 09, Revision D. 1; Gaussian, 2009. Becke, 1993, Density-functional thermochemistry. III. The role of exact exchange, J. Chem. Phys., 98, 5648, 10.1063/1.464913 Lee, 1988, Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density, Phys. Rev. B, 37, 785, 10.1103/PhysRevB.37.785 Zhao, 2006, Design of density functionals by combining the method of constraint satisfaction with parametrization for thermochemistry, thermochemical kinetics, and noncovalent interactions, J. Chem. Theory Comput., 2, 364, 10.1021/ct0502763 Zhao, 2008, The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of four M06-class functionals and 12 other function, Theor. Chem. Acc., 120, 215, 10.1007/s00214-007-0310-x Torres, 2012, A (nearly) universally applicable method for modeling noncovalent interactions using B3LYP, J. Phys. Chem. Lett., 3, 1738, 10.1021/jz300554y DiLabio, 2013, Extension of the B3LYP-dispersion-correcting potential approach to the accurate treatment of both inter- and intra-molecular interactions, Theor. Chem. Acc., 132, 1389, 10.1007/s00214-013-1389-x Konya, 2000, Laser flash photolysis studies on the first superoxide thermal source. First direct measurements of the rates of solvent-assisted 1,2-hydrogen atom shifts and a proposed new mechanism for this unusual rearrangement, J. Am. Chem. Soc., 122, 7518, 10.1021/ja993570b G.A. Andrienko, Chemcraft, 2015 <http://www.chemcraftprog.com>. Marenich, 2009, Universal solvation model based on solute electron density and a continuum model of the solvent defined by the bulk dielectric constant and atomic surface tensions, J. Phys. Chem. B, 113, 6378, 10.1021/jp810292n Abraham, 1990, Hydrogen-bonding. 10. A scale of solute hydrogen-bond basicity using log k values for complexation in tetrachloromethane, Chem. Soc., Perkin Trans., 2, 521, 10.1039/p29900000521 Galano, 2013, A computational methodology for accurate predictions of rate constants in solution: application to the assessment of primary antioxidant activity, J. Comput. Chem., 34, 2430, 10.1002/jcc.23409 DiLabio, 2007, Lone pair-π and π–π interactions play an important role in proton-coupled electron transfer reactions, J. Am. Chem. Soc., 129, 6199, 10.1021/ja068090g DiLabio, 2005, A theoretical study of the iminoxyl/oxime self-exchange reaction. A five-center, cyclic proton-coupled electron transfer, J. Am. Chem. Soc., 127, 6693, 10.1021/ja0500409 Mayer, 2002, Proton-coupled electron transfer versus hydrogen atom transfer in benzyl/toluene, methoxyl/methanol, and phenoxyl/phenol self-exchange reactions, J. Am. Chem. Soc., 124, 11142, 10.1021/ja012732c Mayer, 2004, Proton-coupled electron transfer: a reaction chemist’s view, Annu. Rev. Phys. Chem., 55, 363, 10.1146/annurev.physchem.55.091602.094446