Radical-scavenging activity of the reaction products of isoeugenol with thiol, thiophenol, mercaptothiazoline or mercaptomethylimidazole using the induction period method

The reaction products in the presence of Lewis acid of isoeugenol (1) with ethanethiol, thiophenol, 2-mercaptothiazoline or 2-mercapto-1-methylimidazole (ISO-S1-ISO-S-4) were obtained. The radical-scavenging activity of these compounds was investigated using the induction period method for polymerization of methyl methacrylate (MMA) initiated by thermal decomposition of 2,2'-azobisisobutyronitrile (AIBN) and benzoyl peroxide (BPO) and monitored by differential scanning calorimetry (DSC). For BPO, the stoichiometric factor (number of free radicals trapped by one mole of antioxidant moiety, n) declined in the order isoeugenol (1.8) > ISO-S-1 (1.6) > ISO-S-2 (1.2) > ISOS- 3 (0.9) > ISO-S-4 (0.3), whereas for AIBN, their n values were about 1, except for ISOS- 3 (0.6). The ratio of the rate constant of inhibition to that of propagation (k(inh)/k(p)) for BPO declined in the order ISO-S-4 (56) > ISO-S-3 (15) > ISO-S-2 (11) >ISO-S-1 (9) > isoeugenol (8). Similarly, for AIBN the k(inh)/k(p) of the reaction products (33-57) was greater than that of isoeugenol (31). The reaction products of isoeugenol with a SH group showed greater inhibition rate constants (kinh) than the parent compound isoeugenol.     

Polypyrroles as antioxidants: kinetic studies on reactions of bilirubin and biliverdin dimethyl esters and synthetic model compounds with peroxyl radicals in solution. Chemical calculations on selected typical structures

[reaction: see text] Rate constants for hydrogen-atom transfer (HAT) from bilirubin dimethyl ester (BRDE) and biliverdin dimethyl ester (BVDE) to peroxyl radicals during inhibited autoxidation of styrene initiated by azo-bisisobutyronitrile (AIBN) were k(inh)(BRDE) = 22.5 x 10(4) and k(inh)(BVDE) = 10.2 x 10(4) M(-1) s(-1), and the stoichiometric factors (n) were 2.0 and 2.7, respectively. A synthetic tetrapyrrole (bis(dipyrromethene)) containing the alpha-central (2,2') CH2 linkage gave k(inh) = 39.9 x 10(4) M(-1) s(-1) and n = 2.3, whereas the beta-linked (3,3') isomer was not an active antioxidant. Several dipyrrinones were synthesized as mimics of the two outer heterocyclic rings of bilirubin and biliverdin. The dipyrrinones containing N-H groups in each ring were active antioxidants, whereas those lacking two such "free" N-H groups, such as N-CH3 dipyrrinones and dipyrromethenes, did not exhibit antioxidant activity. Overall, the relative k(inh) values compared to those of phenolic antioxidants, 2,6-di-tert-butyl-4-methoxyphenol (DBHA) and 2,6-di-tert-butyl-4-methylphenol (BHT), were 2,2'-bis(dipyrromethene) > BRDE > DBHA > dipyrrinones > BVDE > BHT. This general trend in antioxidant activities was also observed for the inhibited autoxidation of cumene initiated by AIBN. Chemical calculations of the N-H bond dissociation enthalpies (BDEs) of the typical structures support a HAT mechanism from N-H groups to trap peroxyl radicals. Intramolecular hydrogen bonding of intermediate nitrogen radicals has a major influence on the antioxidant activities of all compounds studied. Indeed, chemical calculations showed that the initial nitrogen radical from a dipyrrinone is stabilized by 9.0 kcal/mol because of H-bonding between the N-H remaining on one ring and the ground-state pyrrolyl radical of the adjacent ring in the natural zusammen structure. The calculated minimum structure of bilirubin shows strong intramolecular H-bonding of the N-H groups with carbonyl groups resulting in the known "ridge-tile" structure which is not an active HAT antioxidant. The calculated minimum structure of biliverdin is planar. BRDE is readily converted into BVDE by reaction with the electron-deficient DPPH* radical under argon in chlorobenzene. An electron-transfer mechanism is proposed for the initiating step in this reaction, and this is supported by the relatively low ionizing potential of a model dipyrrole representing the two central rings of bilirubin.     

Exchange of organic radicals with organo-cobalt complexes formed in the living radical polymerization of vinyl acetate

Exchange of organic radicals between solution and organo-cobalt complexes is experimentally observed and the reaction pathway is probed through DFT calculations. Cyanoisopropyl radicals from AIBN (2,2'-azobisisobutyronitrile) enter solutions of cobalt(II) tetramesityl porphyrin ((TMP)Co(II)*, 1) and vinyl acetate (VAc) in benzene and react to produce transient hydride (TMP)Co-H and radicals (*CH(OAc)CH2C(CH3)2CN (R1*)) that proceed on to form organo-cobalt complexes (TMP)Co-CH(OAc)CH3 (4, Co-R2) and (TMP)Co-CH(OAc)CH2C(CH3)2CN (3, Co-R1), respectively. Rate constants for cyanoisopropyl radical addition with vinyl acetate and hydrogen atom transfer to (TMP)Co(II)* are reported through kinetic studies for the formation and transformation of organo-cobalt species in this system. Rate constants for near-degenerate exchanges of radicals in solution with organo-cobalt complexes are deduced from (1)H NMR studies and kinetic modeling. DFT computations revealed formation of an unsymmetrical adduct of (TMP)Co-CH(OAc)CH3 (4) with *CH(OAc)CH3 (R2*) and support an associative pathway for radical interchange through a three-centered three-electron transition state [R...Co...R]. Associative radical interchange of the latent radical groups in organo-cobalt porphyrin complexes with freely diffusing radicals in solution that is observed in this system provides a pathway for mediation of living radical polymerization of vinyl acetate.     

Selective Activation of C=C Bond in Sustainable Phenolic Compounds from Lignin via Photooxidation: Experiment and Density Functional Theory Calculations

Lignocellulosic biomass can be converted to high‐value phenolic compounds, such as food additives, antioxidants, fragrances and fine chemicals. We investigated photochemical and heterogeneous photocatalytic oxidation of two isomeric phenolic compounds from lignin, isoeugenol and eugenol, in several nonprotic solvents, for the first time by experiment and the density functional theory (DFT) calculations. Photooxidation was conducted under ambient conditions using air, near‐UV light and commercial P25 TiO₂ photocatalyst, and the products were determined by TLC, UV–Vis absorption spectroscopy, HPLC‐UV and HPLC‐MS. Photochemical and photocatalytic oxidation of isoeugenol proceeds via the mild oxidative “dimerization” to produce the lignan dehydrodiisoeugenol (DHDIE), while photooxidation of eugenol does not proceed. The DFT calculations suggest a radical stepwise mechanism for the oxidative “dimerization” of isoeugenol to DHDIE as was calculated for the first time.     

Preparation of Polystyrenylphosphonous Acid of Low Polymerization Degree and Influence of Initiators upon the Free Radical Reaction Mechanism

Organophosphorus chemistry plays an important role in chemical engineering, pesticide, medicine and catalysis1,2. In recent years, after extensive research and widespread application, synthesis and preparation of new organophosphorus compounds have attracted increasing research interest. Polystyrene is a very important and versatile matrix or precursor of various kinds of functional polymer. Usually, introducing of phosphonic PO3H2 or phosphinic PO2H2 group into polystyrene matrix through…     

A temperature-dependent relative-rate study of the OH initiated oxidation of n-butane: the kinetics of the reactions of the 1- and 2-butoxy radicals

The kinetics of the reactions of 1-and 2-butoxy radicals have been studied using a slow-flow photochemical reactor with GC-FID detection of reactants and products. Branching ratios between decomposition, CH3CH(O*)CH2CH3 --> CH3CHO + C2H5, reaction (7), and reaction with oxygen, CH3CH(O*)CH2CH3+ O2 --> CH3C(O)C2H5+ HO2, reaction (6), for the 2-butoxy radical and between isomerization, CH3CH2CH2CH2O* --> CH2CH2CH2CH2OH, reaction (9), and reaction with oxygen, CH3CH2CH2CH2O* + O2 --> C3H7CHO + HO2, reaction (8), for the 1-butoxy radical were measured as a function of oxygen concentration at atmospheric pressure over the temperature range 250-318 K. Evidence for the formation of a small fraction of chemically activated alkoxy radicals generated from the photolysis of alkyl nitrite precursors and from the exothermic reaction of 2-butyl peroxy radicals with NO was observed. The temperature dependence of the rate constant ratios for a thermalized system is given by k7/k6= 5.4 x 10(26) exp[(-47.4 +/- 2.8 kJ mol(-1))/RT] molecule cm(-3) and k9/k8= 1.98 x 10(23) exp[(-22.6 +/- 3.9 kJ mol(-1))/RT] molecule cm(-3). The results agree well with the available experimental literature data at ambient temperature but the temperature dependence of the rate constant ratios is weaker than in current recommendations.     

Quantum chemical and master equation simulations of the oxidation and isomerization of vinoxy radicals

The vinoxy radical, a common intermediate in gas-phase alkene ozonolysis, reacts with O2 to form a chemically activated alpha-oxoperoxy species. We report CBS-QB3 energetics for O2 addition to the parent (*CH2CHO, 1a), 1-methylvinoxy (*CH2COCH3, 1b), and 2-methylvinoxy (CH3*CHCHO, 1c) radicals. CBS-QB3 predictions for peroxy radical formation agree with experimental data, while the G2 method systematically overestimates peroxy radical stability. RRKM/master equation simulations based on CBS-QB3 data are used to estimate the competition between prompt isomerization and thermalization for the peroxy radicals derived from 1a, 1b, and 1c. The lowest energy isomerization pathway for radicals 4a and 4c (derived from 1a and 1c, respectively) is a 1,4-shift of the acyl hydrogen requiring 19-20 kcal/mol. The resulting hydroperoxyacyl radical decomposes quantitatively to form *OH. The lowest energy isomerization pathway for radical 4b (derived from 1b) is a 1,5-shift of a methyl hydrogen requiring 26 kcal/mol. About 25% of 4a, but only approximately 5% of 4c, isomerizes promptly at 1 atm pressure. Isomerization of 4b is negligible at all pressures studied.     

Trapping effect of eugenol on hydroxyl radicals induced by L-DOPA in vitro

Many researchers have stated that eugenol might inhibit lipid peroxidation at the stage of initiation, propagation, or both, and many attempts have been made to elucidate the mechanism of its antioxidant activity. Nevertheless, details of its mechanism are still obscure. This study was carried out to investigate the trapping effect of eugenol on hydroxyl radical generated from L-3,4-dihydroxyphenylalanine (DOPA) in MiliQ water and the generation mechanism of the hydroxyl radical by this system which uses no metallic factor. This was studied by adding L-DOPA and 5,5-dimethyl-1-pyrroline N-oxide (DMPO) to phosphate buffered saline (PBS) or MiliQ water, and the generation of hydroxyl radical was detected on an ESR spectrum. By this method, the effect of antioxidants was detected as a modification of ESR spectra. We found that the eugenol trapped hydroxyl radicals directly, because it had no iron chelating action, did not trap L-DOPA semiquinone radical and inhibited hydroxyl radicals with or without iron ion.     

Study of the reaction products of flavonols with 2,2-diphenyl-1-picrylhydrazyl using liquid chromatography coupled with negative electrospray ionization tandem mass spectrometry

The products obtained after the reaction between flavonols and the stable free radical 2,2-diphenyl-1-picrylhydrazyl (DPPH(*)) in both methanol and acetonitrile were characterized using liquid chromatography coupled with negative electrospray ionization tandem mass spectrometry (LC/ESI-MS/MS) and NMR spectroscopy. The flavonols studied were quercetin, kaempferol and myricetin. In methanol, two reaction products of oxidized quercetin were identified using LC/ESI-MS/MS and NMR. Quercetin was oxidized through a transfer of two H-atoms to DPPH(*) and subsequently incorporated either two CH(3)OH molecules or one CH(3)OH- and one H(2)O molecule giving the products 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-2,3-dimethoxy-2,3-dihydrochromen-4-one and 2-(3,4-dihydroxyphenyl)-3,3,5,7-tetrahydroxy-2-methoxy-2,3-dihydrochromen-4-one, respectively. LC/ESI-MS/MS analysis revealed that in methanol, kaempferol and myricetin also gave rise to methoxylated oxidation products similar to that identified for quercetin. Kaempferol, in addition, also exhibited products where a kaempferol radical, obtained by a transfer of one H-atom to DPPH(*), reacted with CH(3)OH through the addition of CH(3)O(*), yielding two isomeric products. When the reaction took place in acetonitrile, LC/ESI-MS/MS analysis showed that both quercetin and myricetin formed stable isomeric quinone products obtained by a transfer of two H-atoms to DPPH(*). In contrast, kaempferol formed two isomeric products where a kaempferol radical reacted with H(2)O through the addition of OH(*), i.e. similar to the reaction of kaempferol radicals with CH(3)OH.     

Fundamental studies of grafting reactions in free radical copolymerization. III. Grafting of styrene,acrylate, and methacrylate monomers onto cis-polybutadiene using benzoyl peroxide initiator in solution polymerization

Benzoyl peroxide (BPO), due to its higher radical reactivity as compared to AIBN, is known to promote grafting onto cis-polybutadiene. Switching from AIBN to BPO initiator made a dramatic difference in the extent of grafting for styrene and methacrylate monomers, but only a modest difference for acrylate monomer. For styrene and methacrylate monomers, graft site formation is due to BPO initiator radical attack onto the backbone via allylic hydrogen abstraction. Significant levels of grafting are achieved and depend upon the relative concentrations of monomer and backbone polymer but not upon the level of initiator. For acrylic monomer, graft site formation was found to be due to polymer radical attack at the double bond in the backbone. Abstraction of allylic hydrogen also occurs but results in retardation of the overall reaction rate. Graft level was dependent upon initiator and back-bone polymer concentrations but not upon monomer concentration. The effective role of the initiator is only to produce polymer radicals; the BPO has no direct role in the formation of effective graft sites. © 1995 John Wiley & Sons, Inc.     

Antioxidant activity and kinetics studies of eugenol and 6-bromoeugenol

In this work, we report the antioxidant and free radical scavenging activity of 6-bromoeugenol and eugenol. EC₅₀, the concentration providing 50% inhibition, is calculated and the antioxidant activity index (AAI) is evaluated. The antioxidant activity was evaluated using 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical-scavenging method. EC₅₀ values of 6-bromoeugenol, ascorbic acid and eugenol were 34.270 μg/mL, 54.888 μg/mL and 130.485 μg/mL, respectively. 6-Bromoeugenol showed higher AAI value (1.122) followed by ascorbic acid (0.700), then by eugenol (0.295). We also investigate the kinetics of DPPH radical scavenging activity of our products to determine the useful parameter TEC₅₀ to evaluate their antiradical efficiency (ARE). Our results have shown high ARE. This study has provided the following ARE ( × 10^? 3) order for the tested antioxidants: ascorbic acid (70.119)>6-bromoeugenol (34.842) > eugenol (21.313). Finally, we classify ascorbic acid and eugenol as fast kinetics reaction (TEC₅₀ 8.82 and 11.38 min, respectively) and 6-bromoeugenol as medium kinetics reaction (TEC₅₀ 39.24 min).     

不同引发剂引发SBS接枝马来酸酐的机理研究

采用FTIR和1 H NMR研究了引发剂过氧化二苯甲酰 (BPO)和偶氮二异丁腈 (AIBN)对聚苯乙烯 聚丁二烯 聚苯乙烯 (SBS)接枝马来酸酐 (MAH)的影响 ,讨论了相应的接枝机理 ,通过丁二烯 (PB)段碳碳双键(CC)随接枝率变化的规律进一步验证了机理 .结果表明 ,BPO与AIBN引发接枝的机理不同 ,BPO可引发PB的双键和烯丙位碳氢键 ,但引发烯丙位的速率比引发双键大 ;当BPO浓度达到一定量时 ,大量烯丙位的引发保护了碳碳双键 ,随BPO浓度的增大 ,碳碳双键的含量先减少后增加 .AIBN不能引发PB段烯丙位的碳氢键 ,只能引发双键接枝     

Antioxidative properties of hydroxycinnamic acid derivatives and a phenylpropanoid glycoside. A pulse radiolysis study

Spectral and redox properties of the phenoxyl radicals from hydroxycinnamic acid derivatives and one selected component of phenylpropanoid glycosides, verbascoside, were studied using pulse radiolysis techniques. On the basis of the pH dependence of phenoxyl radical absorptions, the pK_a values for deprotonation of sinapic acid radical and ferulic acid radical are 4.9 and 5.2. The rate constants of one electron oxidation of those antioxidants by azide radical and bromide radical ion were determined at pH 7. The redox potentials of those antioxidants were determined as 0.59–0.71 V vs NHE at pH 7 with reference standard 4-methoxyphenol and resorcinol.     

Experimental and theoretical study of the structures and binding energies of eugenol (H2O)n, n=0-2

Eugenol (4-Allyl-2-methoxyphenol), a phenol-derivative with an intramolecular -OH ...OCH(3) hydrogen bond (H bond), has been studied in a supersonic expansion using a number of complementary laser spectroscopic techniques. The mass-resolved excitation spectrum of eugenol and its water complexes are reported for the first time. The most intense set of bands on the resonantly enhanced multiphoton ionization (REMPI) spectrum of eugenol originate in a conformer whose S(1)<--S(0) transition is at 35 202 cm(-1) and the ionization threshold at (I(0)<--S(0)) 62 544+/-150 cm(-1) (7.755+/-0.019 eV). In addition, two low intensity features redshifted with respect to the 0(0) (0) transition have been identified as due to a second, less stable conformer. Ab initio calculations show that the potential energy landscape depicts at least three minima associated with one folded and two extended conformers, one of which is the most stable. Clusters of eugenol/water were prepared in a supersonic expansion by seeding eugenol and water in noble gas He and examined by two-color REMPI (R2PI) and IR-UV double resonance spectroscopies. Only one single isomer was observed for both 1:1 and 1:2 complexes, in contrast with the several stable conformers provided by the computations. The dissociation energies of the 1:1 and 1:2 complexes have been determined by the fragmentation threshold method and the results compared with those from ab initio calculations conducted at the B3LYP and MP2 levels with a variety of basis sets.     

Kinetic studies on stilbazulenyl-bis-nitrone (STAZN), a nonphenolic chain-breaking antioxidant in solution, micelles, and lipid membranes

The rate constants, k(inh), for reaction of stilbazulenyl-bis-nitrone (STAZN, 1) with peroxyl radicals and the number of radicals trapped, n, are compared with those of phenolic antioxidants 2,2,5,7,8-pentamethyl-6-hydroxychroman (PMHC, 4a), 2,5,7,8-tetramethyl-6-hydroxychroman-2-carboxylic acid (Trolox, 4b), and 2,6-di-tert-butyl-4-methoxyphenol (DBHA, 5). The behavior of STAZN depended markedly on the media and type of initiator used, water-soluble or lipid-soluble. In styrene/chlorobenzene and initiation by azo-bis(isobutyronitrile) (AIBN), k(inh) (STAZN) = 0.64 k(inh) (5) = 0.02k(inh) (4a). On addition of methanol, the k(inh) of STAZN increased 6-fold to be four times that of 5 while that of 4a decreased 6-fold. In aqueous SDS-micelles containing methyl linoleate and initiation with water-soluble azo-bis(amidinopropane)2HCl, ABAP, the relative k(inh) values were 1 >or= 4b > 5. In dilinoleoylphosphatidyl choline (DLPC) bilayers and initiation with lipid-soluble azo-bis-2,4(dimethylvaleronitrile) (DMVN), the k(inh) order was 5 > 4b > 1. During initiation with ABAP in micelles and bilayers, the calculated values of k(inh) for STAZN changed during the induction period. The experimental results are interpreted in terms of the conformation of STAZN, which is transoid in homogeneous solution but cisoid in aqueous dispersions of lipids. In such dispersions, the STAZN lies at the lipid-water interface where it traps water-soluble peroxyl radicals by a single electron-transfer mechanism. The cisoid conformation at lipid-water interfaces is supported by theoretical calculations.     

Potent 2,2-diphenyl-1-picrylhydrazyl radical-scavenging activity of novel antioxidants, double-stranded tyrosine residues conjugating pyrocatechol

New potent antioxidants conjugating the catechol (=pyrocatechol; pyrCat) group to two N-termini of modified double-stranded tyrosine residues were synthesized and showed radical scavenging activity with 2,2-diphenyl-1-picrylhydrazyl radical (DPPH radical, DPPH˙) as a free radical model, second-order rate constants for the DPPH˙ scavenging reaction, and the results from electron spin resonance (ESR) studies. It was found that the tyrosine (Tyr) residue and pyrCat containing new antioxidants developed in the study have about 3-20 times more potent antioxidative activity than Trolox, pyrCat, and L-ascorbic acid (VC). In order to elucidate the relationship between antioxidant activity and the molecular orbital states, and to design potent antioxidants we present an interesting approach using an absolute hardness (η)-absolute electronegativity (χ) diagram based on chemical hardness. It was shown that quantum chemicals were required to develop potent antioxidants.     

羧基化氧化石墨烯的可控合成及血液相容性

采用自由基引发剂偶氮二异丁腈(AIBN)作为功能改性剂, 通过AIBN分解产生的异丁腈自由基进攻氧化石墨烯上五元环与七元环的缺陷点, 形成氰基改性氧化石墨烯中间体, 再通过水解反应制得羧基化氧化石墨烯[GeneO-C(CH₃)₂-COOH]纳米材料. 采用傅里叶变换红外光谱(FTIR), X射线衍射(XRD), 热重分析(TGA)和原子力显微镜(AFM)等方法对合成的材料进行了表征, 并采用复钙时间测试考察了材料的血液相容性. 研究结果表明, 氧化石墨烯中羧基的含量可以通过调整AIBN和GeneO的投料比来控制. 本方法不但可提高氧化石墨烯的羧基含量, 而且可使其具有良好的血液相容性.     

Novel diastereoselective synthesis of bicyclic beta-lactams through radical cyclization and their reduction toward 2-(1-alkoxy-2-hydroxyethyl)piperidines and 2-(1-alkoxy-2-hydroxyethyl)azepanes

1-Allyl- and 1-(3-phenylallyl)-substituted 4-(2-bromo-1,1-dimethylethyl)azetidin-2-ones were transformed into 3-substituted 7-alkoxy-5,5-dimethyl-1-azabicyclo[4.2.0]octane-8-ones through radical cyclization by means of n-tributyltin hydride and AIBN in toluene with excellent diastereocontrol (>or=99%). The radical cyclization of 4-(2-bromo-1,1-dimethylethyl)-1-(2-methylallyl)azetidin-2-ones afforded 8-alkoxy-3,6,6-trimethyl-1-azabicyclo[5.2.0]nonan-9-ones in good diastereomeric excess (75-78%). The reductive ring opening of 1-azabicyclo[4.2.0]octane-8-ones and 1-azabicyclo[5.2.0]nonan-9-ones with lithium aluminum hydride resulted in novel 2-(1-alkoxy-2-hydroxyethyl)piperidines and -azepanes, which were isolated as single isomers.     

Determination of reactions between free radicals and selected Chilean wines and transition metals by ESR and UV-vis technique

Four different types of Chilean wines (Cabernet Sauvignon, Merlot, Carmenere and Syrah) were selected and examined in their free radical scavenging capacities by electron spin resonance (ESR) and spectrophotometric methods. The free radical scavenging properties were evaluated against 2,2-diphenyl-1-picrylhydrazyl (DPPH*) radical, 2,6-di-tert-butyl-alpha-(3,5-di-tert-butyl-4-oxo-2,5-cyclohexadien-1-ylidene)-p-tolyloxy (Galvinoxyl) radical and hydroxyl radical (HO*). The possible effect on these scavenging properties of added transition metals to these wines was evaluated. Among the wines evaluated, Cabernet Sauvignon was the one with the highest activity against all radicals tested. The presence of added copper or iron to wines resulted in a reduced free radical scavenging capacity for all type of wines studied. The formation of redox inactive complexes between polyphenols of wine and transition metals is the possible cause of this reduction in antioxidant activity.     

Kinetic and redox characteristics of phenoxyl radicals of eugenol and isoeugenol: A pulse radiolysis study

The phenoxyl radicals of eugenol (EgOH) and isoeugenol (iEgOH) were generated by the specific one‐electron oxidant N₃^· using pulse radiolysis technique, and were characterized by their absorption spectra, decay and formation kinetics, and one‐electron reduction potential (E₇¹) values. Reactivities of eugenol phenoxyl radical with the biologically important molecule, trolox C (analogue of vitamin E, α‐tocopheral), were determined. Reactions of OH with these phenols were studied at different pHs and suitable mechanisms for these reactions were suggested. Scavenging abilities of the phenols toward highly damaging Br^·, NO₂^·, and CCl₃O₂^· radicals were evaluated. © 2000 John Wiley & Sons, Inc. Int J Chem Kinet 32: 17–23, 2000