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Cyclic voltammetry (CV) was used to investigate their electrochemical properties and showed a more pronounced substituent effect for oxidation than for reduction. Rate constants of superoxide radical (O2\u2022\u2013) reactions with nitrones were determined using a UV\u2013vis stopped-flow method, and phenyl radical (Ph\u2022) trapping rate constants were measured by EPR spectroscopy. The effect of N-tert-butyl substitution on the charge density and electron density localization of the nitronyl carbon as well as on the free energies of nitrone reactivity with O2\u2022\u2013 and HO2\u2022 were computationally rationalized at the PCM\/B3LYP\/6-31+G**\/\/B3LYP\/6-31G* level of theory. Theoretical and experimental data showed that the rates of the reaction correlate with the nitronyl carbon charge density, suggesting a nucleophilic nature of O2\u2022\u2013 and Ph\u2022 addition to the nitronyl carbon atom. Finally, the substituent effect was investigated in cell cultures exposed to hydrogen peroxide and a correlation between the cell viability and the oxidation potential of the nitrones was observed. Through a combination of computational methodologies and experimental methods, new insights into the reactivity of free radicals with nitrone derivatives have been proposed.<\/jats:p>","DOI":"10.1021\/jo501121g","type":"journal-article","created":{"date-parts":[[2014,6,26]],"date-time":"2014-06-26T10:35:57Z","timestamp":1403778957000},"page":"6615-6626","source":"Crossref","is-referenced-by-count":27,"title":["Reactivities of Substituted\n\u03b1-Phenyl-\n                    <i>N<\/i>\n                    -\n                    <i>tert<\/i>\n                    -butyl Nitrones"],"prefix":"10.1021","volume":"79","author":[{"given":"Marie","family":"Rosselin","sequence":"first","affiliation":[{"name":"Avignon Universite\u0301 , , 33 rue Louis Pasteur , ,","place":["Avignon, France, F-84000"]},{"name":"Institut des Biomole\u0301cules Max Mousseron (UMR 5247) , 15 avenue Charles Flahault , ,","place":["Montpellier Cedex 05, France, F-34093"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Fanny","family":"Choteau","sequence":"additional","affiliation":[{"name":"Avignon Universite\u0301 , , 33 rue Louis Pasteur , ,","place":["Avignon, France, F-84000"]},{"name":"Institut des Biomole\u0301cules Max Mousseron (UMR 5247) , 15 avenue Charles Flahault , ,","place":["Montpellier Cedex 05, France, F-34093"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kamal","family":"Ze\u0301amari","sequence":"additional","affiliation":[{"name":"Aix-Marseille Universite\u0301-CNRS , , avenue Escadrille Normandie-Niemen , ,","place":["Marseille Cedex 20, France, F-13397"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kevin M.","family":"Nash","sequence":"additional","affiliation":[{"name":"The Ohio State University , , , ,","place":["Columbus, Ohio, United States, 43210"]},{"name":"The Ohio State University , , , ,","place":["Columbus, Ohio, United States, 43210"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Amlan","family":"Das","sequence":"additional","affiliation":[{"name":"The Ohio State University , , , ,","place":["Columbus, Ohio, United States, 43210"]},{"name":"The Ohio State University , , , ,","place":["Columbus, Ohio, United States, 43210"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Robert","family":"Lauricella","sequence":"additional","affiliation":[{"name":"Aix-Marseille Universite\u0301-CNRS , , avenue Escadrille Normandie-Niemen , ,","place":["Marseille Cedex 20, France, F-13397"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Elisabeth","family":"Lojou","sequence":"additional","affiliation":[{"name":"CNRS-Aix-Marseille Universite\u0301 , , 31 chemin Joseph Aiguier , ,","place":["Marseille Cedex 20, France, F-13402"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Be\u0301atrice","family":"Tuccio","sequence":"additional","affiliation":[{"name":"Aix-Marseille Universite\u0301-CNRS , , avenue Escadrille Normandie-Niemen , ,","place":["Marseille Cedex 20, France, F-13397"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Frederick A.","family":"Villamena","sequence":"additional","affiliation":[{"name":"The Ohio State University , , , ,","place":["Columbus, Ohio, United States, 43210"]},{"name":"The Ohio State University , , , ,","place":["Columbus, Ohio, United States, 43210"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Gre\u0301gory","family":"Durand","sequence":"additional","affiliation":[{"name":"Avignon Universite\u0301 , , 33 rue Louis Pasteur , ,","place":["Avignon, France, F-84000"]},{"name":"Institut des Biomole\u0301cules Max Mousseron (UMR 5247) , 15 avenue Charles Flahault , ,","place":["Montpellier Cedex 05, France, F-34093"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2014,6,26]]},"reference":[{"key":"2026090305473796100_cit1","doi-asserted-by":"crossref","first-page":"619","DOI":"10.1089\/152308604773934387","volume":"6","author":"Villamena","year":"2004","journal-title":"Antioxid. 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