{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,27]],"date-time":"2026-03-27T06:17:32Z","timestamp":1774592252602,"version":"3.50.1"},"reference-count":42,"publisher":"Wiley","issue":"17","license":[{"start":{"date-parts":[[2006,3,14]],"date-time":"2006-03-14T00:00:00Z","timestamp":1142294400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2006,6,2]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Fullerene derivatives incorporating one or two 3,5\u2010di\u2010<jats:italic>tert<\/jats:italic>\u2010butyl\u20104\u2010hydroxyphenyl groups were synthesized by 1,3\u2010dipolar cycloaddition of azomethine ylides to C<jats:sub>60<\/jats:sub>. The O\uf8ffH bond dissociation enthalpies (BDEs) of these compounds were estimated by studying, by means of EPR spectroscopy, the equilibration of each of these phenols and 2,6\u2010di\u2010<jats:italic>tert<\/jats:italic>\u2010butyl\u20104\u2010methylphenol (BHT) with the corresponding phenoxyl radicals. The antioxidant activity of the investigated phenols was also determined by measuring the rate constants for their reaction with peroxyl radicals in controlled autoxidation experiments and compared to that recorded under identical experimental settings for [60]fullerene itself and unlinked BHT. The results indicate that linking of the BHT structure to C<jats:sub>60<\/jats:sub> does not substantially alter the thermochemistry and kinetics of its reaction with peroxyl radicals, but such adducts may behave as interesting bimodal radical scavengers. The inherent rate constant for trapping of peroxyl radicals by C<jats:sub>60<\/jats:sub> per se (<jats:italic>k<\/jats:italic><jats:sub>inh<\/jats:sub>=3.1\u00b11.1\u00d710<jats:sup>2<\/jats:sup><jats:sc>\u2009m<\/jats:sc><jats:sup>\u22121<\/jats:sup>\u2009s<jats:sup>\u22121<\/jats:sup>) indicates that, contrary to previous reports, [60]fullerene is an extremely weak chain\u2010breaking antioxidant.<\/jats:p>","DOI":"10.1002\/chem.200501495","type":"journal-article","created":{"date-parts":[[2006,3,14]],"date-time":"2006-03-14T05:53:58Z","timestamp":1142315638000},"page":"4646-4653","source":"Crossref","is-referenced-by-count":61,"title":["Synthesis and Antioxidant Activity of [60]Fullerene\u2013BHT Conjugates"],"prefix":"10.1002","volume":"12","author":[{"given":"Roger F.","family":"Enes","sequence":"first","affiliation":[]},{"given":"Augusto C.","family":"Tom\u00e9","sequence":"additional","affiliation":[]},{"given":"Jos\u00e9 A. S.","family":"Cavaleiro","sequence":"additional","affiliation":[]},{"given":"Riccardo","family":"Amorati","sequence":"additional","affiliation":[]},{"given":"Maria Grazia","family":"Fumo","sequence":"additional","affiliation":[]},{"given":"Gian Franco","family":"Pedulli","sequence":"additional","affiliation":[]},{"given":"Luca","family":"Valgimigli","sequence":"additional","affiliation":[]}],"member":"311","published-online":{"date-parts":[[2006,5,23]]},"reference":[{"key":"e_1_2_6_1_2","doi-asserted-by":"publisher","DOI":"10.1007\/s00280-003-0726-5"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1007\/PL00014177"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1007\/s00726-003-0048-2"},{"key":"e_1_2_6_4_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0378-8741(01)00396-8"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1016\/S1353-8020(00)00064-X"},{"key":"e_1_2_6_6_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0891-5849(00)00505-0"},{"key":"e_1_2_6_7_2","doi-asserted-by":"publisher","DOI":"10.1006\/bbrc.2000.3715"},{"key":"e_1_2_6_8_2","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.94.17.9434"},{"key":"e_1_2_6_9_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.254.5035.1183"},{"key":"e_1_2_6_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar950120p"},{"key":"e_1_2_6_11_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.biopha.2005.02.004"},{"key":"e_1_2_6_12_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2004.03.003"},{"key":"e_1_2_6_13_2","unstructured":"BHT is the abbreviated name of butylated hydroxytoluene (2 6\u2010di\u2010tert\u2010butyl\u20104\u2010methylphenol)."},{"key":"e_1_2_6_14_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0308-8146(02)00579-4"},{"key":"e_1_2_6_15_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0378-8741(03)00036-9"},{"key":"e_1_2_6_16_2","unstructured":"For instance the rate constant for the reaction (addition) of benzyl radical with [60]fullerene was reported as 1.4\u00d7107\u2009m\u22121\u2009s\u22121at 298 K [17]which can be compared to the value of 4.8\u00d7103\u2009m\u22121\u2009s\u22121measured at the same temperature for hydrogen abstraction from BHT by neophyl radical.[18]"},{"key":"e_1_2_6_17_2","doi-asserted-by":"publisher","DOI":"10.1021\/j100121a002"},{"key":"e_1_2_6_18_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja982405d"},{"key":"e_1_2_6_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo961039i"},{"key":"e_1_2_6_20_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00310a049"},{"key":"e_1_2_6_21_2","volume-title":"Free Radicals, Vol. 2","author":"Howard J. A.","year":"1975"},{"key":"e_1_2_6_22_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200500315"},{"key":"e_1_2_6_23_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja9941072"},{"key":"e_1_2_6_24_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(98)01245-3"},{"key":"e_1_2_6_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00016a056"},{"key":"e_1_2_6_26_2","doi-asserted-by":"crossref","first-page":"68","DOI":"10.1515\/zna-1983-0113","volume":"38","author":"Fischer V.","year":"1983","journal-title":"Naturforsch. A"},{"key":"e_1_2_6_27_2","doi-asserted-by":"publisher","DOI":"10.1039\/b200323f"},{"key":"e_1_2_6_28_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo025755y"},{"key":"e_1_2_6_29_2","unstructured":"All the BDE values determined in benzene solution by means of the EPR radical equilibration technique [19]based on the O\uf8ffH BDE of 2 4 6\u2010tri\u2010tert\u2010butylphenol determined many years earlier by Mahoney et al.[30]using calorimetric measurements must be downscaled by 1.1 kcal\u2009mol\u22121due to the revision of the heat of formation of (E)\u2010azobenzene.[31]"},{"key":"e_1_2_6_30_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja01042a034"},{"key":"e_1_2_6_31_2","doi-asserted-by":"publisher","DOI":"10.1021\/jp047148f"},{"key":"e_1_2_6_32_2","doi-asserted-by":"publisher","DOI":"10.1039\/b105079f"},{"key":"e_1_2_6_33_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo971944i"},{"key":"e_1_2_6_34_2","doi-asserted-by":"publisher","DOI":"10.1016\/0006-2952(89)90186-X"},{"key":"e_1_2_6_35_2","unstructured":"From the measured oxidizability of cumene (1.72\u00d710\u22123\u2009M\u22121\/2\u2009s\u22121\/2) at 30\u2009\u00b0C the propagation rate constantkp[Eq. (6)] can be derived as 0.37\u2009m\u22121\u2009s\u22121."},{"key":"e_1_2_6_36_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00357a024"},{"key":"e_1_2_6_37_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm990144s"},{"key":"e_1_2_6_38_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja027714p"},{"key":"e_1_2_6_39_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.6710156"},{"key":"e_1_2_6_40_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja027986s"},{"key":"e_1_2_6_41_2","unstructured":"Despite the fact that the BDE differences among the investigated compounds are of the same magnitude as the experimental errors it should be considered that these differences were obtained with the same reference phenol (BHT) and thus reflect the actual BDE hierarchic sequence."},{"key":"e_1_2_6_42_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0141-3910(00)00109-9"}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fchem.200501495","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.200501495","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T20:19:53Z","timestamp":1760300393000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.200501495"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2006,5,23]]},"references-count":42,"journal-issue":{"issue":"17","published-print":{"date-parts":[[2006,6,2]]}},"alternative-id":["10.1002\/chem.200501495"],"URL":"https:\/\/doi.org\/10.1002\/chem.200501495","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2006,5,23]]}}}