Summary: A quinone fungicide used for treatment of seeds and foliage.

Top Publications

  1. Duymus H, Arslan M, Kucukislamoglu M, Zengin M. Charge transfer complex studies between some non-steroidal anti-inflammatory drugs and pi-electron acceptors. Spectrochim Acta A Mol Biomol Spectrosc. 2006;65:1120-4 pubmed
    ..with some pi-acceptors, such as tetracyanoethylene (TCNE), 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ), p-chloranil (p-CHL), have been investigated spectrophotometrically in chloroform at 21 degrees C...
  2. Arslan M, Masnovi J. Charge transfer complex formation between p-chloranil and 1,n-di(9-anthryl)alkanes. Spectrochim Acta A Mol Biomol Spectrosc. 2006;64:711-6 pubmed
    ..Charge transfer (CT) complexes of anthracene, 9-methylanthracene and 1,n-di(9-anthryl)alkanes with p-chloranil (p-CHL) have been investigated spectrophotometrically in dichloromethane...
  3. Alqaradawi S, Bazzi H, Mostafa A, Nour E. Synthesis, spectroscopic and thermal investigations of solid charge-transfer complexes of 1,4,7-trimethyl-1,4,7-triazacyclononane and the acceptors iodine, TCNE, TCNQ and chloranil. Spectrochim Acta A Mol Biomol Spectrosc. 2008;71:1594-8 pubmed publisher
    ..The chloranil CT-solid complex cannot be isolated in pure form.
  4. Singh P, Kumar P, Katyal A, Kalra R, Dass S, Prakash S, et al. Synthesis and electrochemical studies of charge-transfer complexes of thiazolidine-2,4-dione with sigma and pi acceptors. Spectrochim Acta A Mol Biomol Spectrosc. 2010;75:983-91 pubmed publisher
    ..novel charge-transfer complexes of thiazolidine-2,4-dione (TZD) with sigma acceptor (iodine) and pi acceptors (chloranil, dichlorodicyanoquinone, picric acid and duraquinone)...
  5. Kim S, Lee J, Lee M, Chung S, Bae O, Chung J. Association of quinone-induced platelet anti-aggregation with cytotoxicity. Toxicol Sci. 2001;62:176-82 pubmed
    ..In one instance, however, p-chloranil demonstrated a potent anti-aggregative effect, but did not induce significant LDH leakage...
  6. Rufino J, Pezza H, Pezza L. Flow-injection spectrophotometric determination of azithromycin in pharmaceutical formulations using p-chloranil in the presence of hydrogen peroxide. Anal Sci. 2008;24:871-6 pubmed
    ..The method is based on the reaction of azithromycin with tetrachloro-p-benzoquinone (p-chloranil) accelerated by hydrogen peroxide and conducted in a methanol medium, producing a purple-red color compound (..
  7. He X, Liu D, Liu R. Sodium borohydride/chloranil-based assay for quantifying total flavonoids. J Agric Food Chem. 2008;56:9337-44 pubmed publisher
    A novel sodium borohydride/chloranil-based (SBC) assay for quantifying total flavonoids, including flavones, flavonols, flavonones, flavononols, isoflavonoids, flavanols, and anthocyanins, has been developed...
  8. Adikwu M, Holtje H. Mechanistic appraisal of the charge-transfer complexes of promethazine with chloranil: a modelling approach. Chem Pharm Bull (Tokyo). 2001;49:669-74 pubmed
    ..capable of pi-pi interaction as well as N-methyl group capable of forming a complex with the weak Lewis acid, p-chloranil. Our modelling studies revealed that the situation where the p-chloranil interacts with a protonated N-methyl ..
  9. Fukuzumi S, Kotani H, Lee Y, Nam W. Sequential electron-transfer and proton-transfer pathways in hydride-transfer reactions from dihydronicotinamide adenine dinucleotide analogues to non-heme oxoiron(IV) complexes and p-chloranil. Detection of radical cations of NADH analogues in acid-. J Am Chem Soc. 2008;130:15134-42 pubmed publisher
    ..Hydride transfer from the NADH analogues to p-chloranil (Cl 4Q) also occurs to produce the corresponding NAD (+) analogues and the hydroquinone anion (Cl 4QH (-))...

More Information


  1. Zhu B, Shan G. Potential mechanism for pentachlorophenol-induced carcinogenicity: a novel mechanism for metal-independent production of hydroxyl radicals. Chem Res Toxicol. 2009;22:969-77 pubmed publisher
  2. Dai M, Rogers J, Warner J, Copley S. A previously unrecognized step in pentachlorophenol degradation in Sphingobium chlorophenolicum is catalyzed by tetrachlorobenzoquinone reductase (PcpD). J Bacteriol. 2003;185:302-10 pubmed
    ..Thus, we proposed and verified experimentally that PcpD is a tetrachlorobenzoquinone reductase that catalyzes the NADPH-dependent reduction of tetrachlorobenzoquinone to tetrachlorohydroquinone. ..
  3. Mostafa A, Bazzi H. Synthesis and spectroscopic studies on charge-transfer molecular complexes formed in the reaction of imidazole and 1-benzylimidazole with ?- and ?-acceptors. Spectrochim Acta A Mol Biomol Spectrosc. 2011;79:1613-20 pubmed publisher
  4. Zhang Q, Xu Y, Wu W, Schramm K, Kettrup A. Reduction of polychlorinated dibenzo- p-dioxins and dibenzofurans levels in chloranil from China. Bull Environ Contam Toxicol. 2002;69:459-62 pubmed
  5. Ferreyra D, Reynoso E, Cordero P, Spesia M, Alvarez M, Milanesio M, et al. Synthesis and properties of 5,10,15,20-tetrakis[4-(3-N,N-dimethylaminopropoxy)phenyl] chlorin as potential broad-spectrum antimicrobial photosensitizers. J Photochem Photobiol B. 2016;158:243-51 pubmed publisher
    ..of the corresponding porphyrin TAPP with p-toluenesulfonhydrazide, followed by selective oxidation with o-chloranil. Spectroscopic properties and the photodynamic activity of these photosensitizers were compared in N,N-..
  6. Wibowotomo B, Eun J, Rhee J. Development of a Sequential Injection Analysis System for the Determination of Saccharin. Sensors (Basel). 2017;17: pubmed publisher
    ..This method is based on the reaction of saccharin with p-chloranil in an ethanol medium with a hydrogen peroxide (H?O?) acceleration, and the resultant violet-red compound was ..
  7. Chakraborty B, Mukherjee A, Seal B. Charge-transfer complex formation between o-chloranil and a series of polynuclear aromatic hydrocarbons. Spectrochim Acta A Mol Biomol Spectrosc. 2001;57:223-9 pubmed
    ..constants, enthalpies and entropies of formation of molecular electron donor-acceptor (EDA) complexes of o-chloranil with a series of aromatic hydrocarbons have been determined spectrophotometrically...
  8. Abraham C, Paull D, Bekele T, Scerba M, Dudding T, Lectka T. A surprising mechanistic "switch" in Lewis acid activation: a bifunctional, asymmetric approach to alpha-hydroxy acid derivatives. J Am Chem Soc. 2008;130:17085-94 pubmed publisher
    ..This new method was applied to the syntheses of several pharmaceutical targets, each of which was obtained in high yield and enantioselectivity. ..
  9. Ezendam J, Vissers I, Bleumink R, Vos J, Pieters R. Immunomodulatory effects of tetrachlorobenzoquinone, a reactive metabolite of hexachlorobenzene. Chem Res Toxicol. 2003;16:688-94 pubmed
    ..Present data show that TCHQ and TCBQ are capable of inducing neoantigen specific T cell help and that TCHQ can induce a compound specific memory response. ..
  10. Wendlandt A, Stahl S. Quinone-Catalyzed Selective Oxidation of Organic Molecules. Angew Chem Int Ed Engl. 2015;54:14638-58 pubmed publisher
    ..Para-quinones with high reduction potentials, such as DDQ and chloranil, are widely used and typically promote hydride abstraction...
  11. O Sullivan S, McCarthy R, Vargo M, Colman R, Sheehan D. Chemical modification at subunit 1 of rat kidney Alpha class glutathione transferase with 2,3,5,6-tetrachloro-1,4-benzoquinone: close structural connectivity between glutathione conjugation activity and non-substrate ligand binding. Biochem Pharmacol. 2006;71:1629-36 pubmed
    ..Homology modelling of rGSTA1-1 modified at Cys-17 of one subunit revealed only modest structural perturbations in the second subunit and tends to exclude global structural effects. ..
  12. Kot M, Zaborska W. Inhibition of jack bean urease by tetrachloro-o-benzoquinone and tetrachloro-p-benzoquinone. J Enzyme Inhib Med Chem. 2006;21:537-42 pubmed
    ..No recovery of urease activity bound in the urease-inhibitor complexes proves that the complexes are stable and strong...
  13. Arslan M, Masnovi J, Krafcik R. Charge-transfer complex formation between p-chloranil and 1,n-dicarbazolylalkanes. Spectrochim Acta A Mol Biomol Spectrosc. 2007;66:1063-7 pubmed
    ..Charge-transfer (CT) complexes of carbazole, N-ethylcarbazole and 1,n-di(N-carbazolyl)alkanes with p-chloranil (p-CHL) have been investigated spectrophotometrically in dichloromethane...
  14. Messerschmidt M, Tschentscher T, Cammarata M, Meents A, Sager C, Davaasambuu J, et al. Ultrafast potential energy surface softening of one-dimensional organic conductors revealed by picosecond time-resolved Laue crystallography. J Phys Chem A. 2010;114:7677-81 pubmed publisher
    ..has been employed to study the structural dynamics of a one-dimensional organic conductor (tetrathiafulvalene-p-chloranil) during photoexcitation in the regime of the neutral to ionic phase transition...
  15. Zhao B, Yang Y, Wang X, Chong Z, Yin R, Song S, et al. Redox-active quinones induces genome-wide DNA methylation changes by an iron-mediated and Tet-dependent mechanism. Nucleic Acids Res. 2014;42:1593-605 pubmed publisher
    ..Moreover, both Tet1/Tet2 knockout and dimethyloxalylglycine-induced Tet inhibition diminished the 5 hmC increase. These results suggest an iron-regulated Tet-dependent DNA demethylation mechanism mediated by redox-active biomolecules. ..
  16. Dutta D, Tummanapelli A. Spectroscopic and computational investigations on the origin of charge transfer between included neutral guest molecules and a functionalized anionic layered host. Phys Chem Chem Phys. 2016;18:22379-89 pubmed publisher
    ..interactions can be used as a driving force for the insertion of neutral guest molecules (ortho- and para-chloranil) within the galleries of an Mg-Al LDH by forming a charge-transfer complex with aniline pre-intercalated as p-..
  17. Giovenzana G, Masciocchi N, Negri R, Palmisano G, Penoni A, Toma L. Quinone-related hexacyclic by-products in the production process of exemestane. Steroids. 2017;120:26-31 pubmed publisher
    ..e., a dehydrogenation to introduce the ?1-unsaturation, is normally performed with quinones such as p-chloranil or DDQ...
  18. Nakamura M, Horiuchi S, Kagawa F, Ogawa N, Kurumaji T, Tokura Y, et al. Shift current photovoltaic effect in a ferroelectric charge-transfer complex. Nat Commun. 2017;8:281 pubmed publisher
    ..Here, we report the photovoltaic effect in an organic molecular crystal tetrathiafulvalene-p-chloranil with a large ferroelectric polarization mostly induced by the intermolecular charge transfer...
  19. Gouda A. Utility of certain sigma- and pi-acceptors for the spectrophotometric determination of ganciclovir in pharmaceutical formulations. Talanta. 2009;80:151-7 pubmed publisher
    ..The recovery percentages ranged from 99.45+/-0.73% to 100.35+/-1.40%. The results were compared favourably with the reported method. ..
  20. Shao J, Huang C, Kalyanaraman B, Zhu B. Potent methyl oxidation of 5-methyl-2'-deoxycytidine by halogenated quinoid carcinogens and hydrogen peroxide via a metal-independent mechanism. Free Radic Biol Med. 2013;60:177-82 pubmed publisher
    ..This is the first report that halogenated quinoid carcinogens and H2O2 can induce potent methyl oxidation of 5mdC via a metal-independent mechanism, which may partly explain their potential carcinogenicity. ..
  21. Pandey R, Mukhopadhyay S, Ramasesha S, Das P. Structure of the pyridine-chloranil complex in solution: a surprise from depolarized hyper-Rayleigh scattering measurements. J Phys Chem B. 2011;115:13842-6 pubmed publisher
    In this article, we report the structure of a 1:1 charge transfer complex between pyridine (PYR) and chloranil (CHL) in solution (CHCl(3)) from the measurement of hyperpolarizability (?(HRS)) and linear and circular depolarization ratios,..
  22. Liu W, Tao F, Zhang W, Li S, Zheng M. Contamination and emission factors of PCDD/Fs, unintentional PCBs, HxCBz, PeCBz and polychlorophenols in chloranil in China. Chemosphere. 2012;86:248-51 pubmed publisher
    The production of chloranil is regarded as a potentially significant source of unintentional POPs...
  23. Medien H, Zahran A. Spectrophotometric kinetic and determination of quinones and barbiturates. Spectrochim Acta A Mol Biomol Spectrosc. 2001;57:2505-11 pubmed
    The kinetics of 1,3-dimethylbarbituric acid with some quinones, namely 1,4-benzoquinone, 1,4-naphthoquinone and p-chloranil in 50% methyl alcohol-water mixture have been investigated spectrophotometrically at 30-50 degrees C...
  24. Yamamoto Y, Itonaga K. Synthesis of chromans via [3 + 3] cyclocoupling of phenols with allylic alcohols using a Mo/o-chloranil catalyst system. Org Lett. 2009;11:717-20 pubmed publisher
    The combination of a molybdenum complex (CpMoCl(CO)(3) or [CpMo(CO)(3)](2)) and o-chloranil was used as a catalyst in the [3 + 3] cyclocoupling of phenols and allylic alcohols under microwave heating conditions...
  25. Balraj C, Ganesh K, Elango K. Molecular complexes of ketaconazole and oxatomide with p-chloranil: spectroscopic and spectrofluorimetric studies. Spectrochim Acta A Mol Biomol Spectrosc. 2011;79:1137-44 pubmed publisher
    ..of the donors ketaconazole (KTZ) and oxatomide (OXA) drugs with 2,3,5,6-tetrachloro-1,4-benzoquinone (p-chloranil, p-CHL) have been investigated spectroscopically (UV-vis, FT-IR and 1H NMR) and spectrofluorimetrically in ..
  26. Alqaradawi S, Nour E. Spectroscopic investigation of the charge-transfer interactions between 1,4,7-trimethyl-1,4,7-triazacyclononane and the acceptors iodine, TCNE, TCNQ and chloranil. Spectrochim Acta A Mol Biomol Spectrosc. 2007;68:908-11 pubmed
    ..pi-acceptors tetracyanoethylene (TCNE), 7,7,8,8-tetracyanoquinodimethane (TCNQ) and tetrachloro-p-benzoquinone (chloranil) have been studied spectrophotometrically and cyclic voltametrically in chloroform at 20 degrees C...
  27. Miyamura H, Maehata K, Kobayashi S. In situ coupled oxidation cycle catalyzed by highly active and reusable Pt-catalysts: dehydrogenative oxidation reactions in the presence of a catalytic amount of o-chloranil using molecular oxygen as the terminal oxidant. Chem Commun (Camb). 2010;46:8052-4 pubmed publisher
    An in situ coupled oxidation cycle that allows catalytic oxidation of a substrate with catalytic amounts of o-chloranil and novel reusable polymer-immobilized platinum nanocluster catalysts using molecular oxygen as the terminal oxidant ..
  28. Sharma K, Sharma S, Lahiri S. Spectrophotometric, Fourier transform infrared spectroscopic and theoretical studies of the charge-transfer complexes between methyldopa [(S)-2 amino-3-(3,4-dihydroxyphenyl)-2-methyl propanoic acid] and the acceptors (chloranilic acid, o-chloranil an. Spectrochim Acta A Mol Biomol Spectrosc. 2012;92:212-24 pubmed publisher
    ..between methyldopa, a centrally acting antihypertensive agent of limited use with the known acceptors like o-chloranil (o-ClN), chloranilic acid (ClA) and dichlorodicyanobenzoquinone (DDQ)...
  29. Ulu S. Rapid and sensitive spectrofluorimetric determination of enrofloxacin, levofloxacin and ofloxacin with 2,3,5,6-tetrachloro-p-benzoquinone. Spectrochim Acta A Mol Biomol Spectrosc. 2009;72:1038-42 pubmed publisher
    ..preparations through charge transfer (CT) complex formation with 2,3,5,6-tetrachloro-p-benzoquinone (chloranil,CLA)...
  30. Ganesh K, Balraj C, Elango K. Spectroscopic and spectrofluorimetric studies on the interaction of irbesartan with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone and iodine. Spectrochim Acta A Mol Biomol Spectrosc. 2011;79:1621-9 pubmed publisher
    ..Solvent variation studies indicated that the binding constant increased with an increase in polarity of the medium. ..
  31. Filatov M. On multiferroicity of TTF-CA molecular crystal. Phys Chem Chem Phys. 2011;13:144-8 pubmed publisher
    ..The dependence of the magnetic coupling parameters on the crystal structure is studied and the implications for experimental observation of magnetic properties of TTF-CA are discussed. ..
  32. Fukuzumi S, Kotani H, Prokop K, Goldberg D. Electron- and hydride-transfer reactivity of an isolable manganese(V)-oxo complex. J Am Chem Soc. 2011;133:1859-69 pubmed publisher
    ..The logarithms of the observed second-order rate constants of hydride transfer (k(H)) from NADH analogues to 1 are linearly correlated with those of hydride transfer from the same series of NADH analogues to p-chloranil.
  33. Zhu B, Mao L, Huang C, Qin H, Fan R, Kalyanaraman B, et al. Unprecedented hydroxyl radical-dependent two-step chemiluminescence production by polyhalogenated quinoid carcinogens and H2O2. Proc Natl Acad Sci U S A. 2012;109:16046-51 pubmed publisher unprecedented two-step CL can be produced by the carcinogenic tetrachloro-1,4-benzoquinone (also known as p-chloranil) and H(2)O(2), which was found to be well-correlated to and directly dependent on its two-step metal-independent ..
  34. Balraj C, Elango K. Spectroscopic studies on the intermolecular charge transfer interaction of Fe(II)- and Fe(III)-phthalocyanines with 2,3,5,6-tetrachloro-1,4-benzoquinone and its application in colorimetric sensing of amino acids and amines. Spectrochim Acta A Mol Biomol Spectrosc. 2012;86:44-50 pubmed publisher
    The interactions of Fe(II)Pc and Fe(III)Pc with ?-acceptor 2,3,5,6-tetrachloro-1,4-benzoquinone (p-chloranil, p-CHL) have been investigated spectroscopically (UV/vis and FT-IR) and spectrofluorimetrically at three different temperatures...
  35. Adikwu M, Ajali U, Okide G, Odoh U. Detection of alpha-methyldopa on thin-layer plates using pi-acceptors in 1,4-dioxane. Boll Chim Farm. 2002;141:315-6 pubmed
    pi-Acceptors (P-chloranil and chloranilic acid) in 1,4-dioxane were used to detect alpha-methyldopa on thin layer plates. Thin layer plates coated to a thickness of 0...
  36. de Lijser H, Rangel N. Photochemical acetalization of carbonyl compounds in protic media using an in situ generated photocatalyst. J Org Chem. 2004;69:8315-22 pubmed
    ..good yields and short reaction times by means of a photochemical reaction in methanol with a catalytic amount of chloranil (2,3,5,6-tetrachloro-1,4-benzoquinone, CA) as the sensitizer...
  37. Vaidyanathan V, Villalta P, Sturla S. Nucleobase-dependent reactivity of a quinone metabolite of pentachlorophenol. Chem Res Toxicol. 2007;20:913-9 pubmed
    ..e., multiple types of adducts are formed. Finally, DNA adducts consistent with Cl4BQ reactions are observed when DNA or dGuo is treated with PCP and a peroxidase-based bioactivating system. ..
  38. de Lijser H, Rangel N, Tetalman M, Tsai C. Mechanistic aspects of the formation of aldehydes and nitriles in photosensitized reactions of aldoxime ethers. J Org Chem. 2007;72:4126-34 pubmed
    ..Nanosecond laser flash photolysis studies have shown that chloranil (CA)-sensitized reactions of the O-methyl (1), O-ethyl (2), O-benzyl (3), and O-tert-butyl (4) benzaldehyde ..
  39. Fu J, Xia X, Liu Z, Wang Y, Wang Y, Shi Q, et al. The acute exposure of tetrachloro-p-benzoquinone (a.k.a. chloranil) triggers inflammation and neurological dysfunction via Toll-like receptor 4 signaling: The protective role of melatonin preconditioning. Toxicology. 2017;381:39-50 pubmed publisher
  40. Ni Y, Zhang Z, Zhang Q, Chen J, Wu Y, Liang X. Distribution patterns of PCDD/Fs in chlorinated chemicals. Chemosphere. 2005;60:779-84 pubmed
    ..and dibenzofurans (PCDD/F) in five chlorinated chemicals (phthalocyanine copper, phthalocyanine green, chloranil-1 and 2, and triclosan), and to compare their 2,3,7,8-tetrachlordibenzo-IpI-dioxin equivalents (TEQ)...
  41. Du L, Chen C, Li J. [Ultraviolet spectral characteristics of charge-transfer reaction complex in micellar system and its application]. Guang Pu Xue Yu Guang Pu Fen Xi. 2005;25:277-9 pubmed
    Charge-transfer (CT) reaction of chloranil (TCBQ) as a pi-electron acceptor with fleroxacin (FLX) as an electron donor has been studied by ultraviolet spectrophotometry method...
  42. Darwish I, Sultan M, Al Arfaj H. Selective kinetic spectrophotometric method for determination of gatifloxacin based on formation of its N-vinyl chlorobenzoquinone derivative. Spectrochim Acta A Mol Biomol Spectrosc. 2010;75:334-9 pubmed publisher
    ..The proposed methods are superior to all the previously reported spectrophotometric methods in terms of the procedure simplicity and assay selectivity. ..
  43. Jiao G, Castro J, Thoresen L, Burgess K. Microwave-assisted syntheses of regioisomerically pure bromorhodamine derivatives. Org Lett. 2003;5:3675-7 pubmed
    ..derivatives (bromorosamines) were prepared via microwave-accelerated condensation reactions followed by oxidation with chloranil. Reaction optimization was conveniently performed by monitoring UV absorptions attributed to the product.
  44. Asker E, Uzkara E, Zeybek O. Effects of methyl substituent on the charge-transfer complexations of dicarbazolylalkanes with p-chloranil, tetracyanoethylene and tetracyanoquinodimethane. Spectrochim Acta A Mol Biomol Spectrosc. 2011;79:1731-8 pubmed publisher
    ..equilibrium constants, enthalpies, and entropies of their charge-transfer (CT) complexes with the ?-acceptors p-chloranil, tetracyanoethylene, and tetracyanoquinodimethane were investigated...
  45. Vaughan P, Novotny P, Haubrich N, McDonald L, Cochran M, Serdula J, et al. Bacterial growth response to photoactive quinones. Photochem Photobiol. 2010;86:1327-33 pubmed publisher
    ..and natural seawater bacterioplankton, growth inhibition was observed when samples were exposed to dichlone, chloranil and sodium anthraquinone-2-sulfonate (AQ2S)...
  46. Bhattacharya S, Banerjee M, Mukherjee A. Room temperature solution studies of complexation between o-chloranil and a series of anilines by spectrophotometric method. Spectrochim Acta A Mol Biomol Spectrosc. 2001;57:2409-16 pubmed
    Electron donor-acceptor (EDA) complex formation between o-chloranil and a series of anilines has been studied in CCl4 medium. In all the cases, EDA complexes are formed instantaneously on mixing the donor and acceptor solutions...
  47. Mostafa A, Bazzi H. Synthesis and spectroscopic studies of the charge transfer complexes of 2- and 3-aminopyridine. Spectrochim Acta A Mol Biomol Spectrosc. 2009;74:180-7 pubmed publisher
    ..DDQ), 2-chloro-1,3,5-trinitrobenzene (picryl chloride, PC), and 2,3,5,6-tetrachloro-1,4-benzoquinone (chloranil) were studied spectrophotometrically in chloroform at room temperature...
  48. Xiong A, Yang L, Zhang F, Yang X, Wang C, Wang Z. Determination of total retronecine esters-type hepatotoxic pyrrolizidine alkaloids in plant materials by pre-column derivatization high-performance liquid chromatography. Biomed Chromatogr. 2009;23:665-71 pubmed publisher
    ..The RET-HPAs reacted with o-chloranil in methanolic solution heated for 3 h, and an oxidative derivative was produced that could be detected at a ..
  49. Alnabari M, Bittner S. New quinone-amino acid conjugates linked via a vinylic spacer. Amino Acids. 2001;20:381-7 pubmed
    b>Chloranil and 2,3-dichloro-1,4-naphthoquinone have been linked to different natural and unnatural amino acids via a vinylic spacer...
  50. Ghosh B, Deb N, Mukherjee A. Determination of individual proton affinities of reserpine from its UV-vis and charge-transfer spectra. J Phys Chem A. 2008;112:6929-35 pubmed publisher
    ..absorption spectra (i) of reserpine itself and (ii) of the charge-transfer (CT) spectra of its complexes with o-chloranil, p-chloranil, and DDQ in aqueous medium (containing 0.1% ethanol v/v)...
  51. Lin P, Nakamura J, Yamaguchi S, Upton P, La D, Swenberg J. Oxidative damage and direct adducts in calf thymus DNA induced by the pentachlorophenol metabolites, tetrachlorohydroquinone and tetrachloro-1,4-benzoquinone. Carcinogenesis. 2001;22:627-34 pubmed
    ..These lesions may have important implications for PCP clastogenicity and carcinogenicity. ..
  52. Darwish I. Development and validation of spectrophotometric methods for determination of fluoxetine, sertraline, and paroxetine in pharmaceutical dosage forms. J AOAC Int. 2005;88:38-45 pubmed
    ..e., chloranil, bromanil, and 2,3-dichloronaphthoquinone, to give colored vinylamino-substituted quinones...
  53. Adikwu M, Holtje H. Charge-oriented modelling in charge-transfer systems. Boll Chim Farm. 2002;141:279-81 pubmed
    ..A modelling approach is applied in this study to examine this mechanism as well as other mechanism. A charge-oriented mechanism is proposed in solvent systems that may not favour this mechanism of interaction. ..
  54. Matos M, Gehlen M. Charge transfer complexes of 9-vinyl-carbazole with pi acceptors in homogeneous and in micellar solutions. Spectrochim Acta A Mol Biomol Spectrosc. 2004;60:1421-6 pubmed
    The molecular association of 9-vinyl-carbazole (CBZ) with three electron acceptors, p-chloranil (CHL), 2,7-dinitro-9-fluorenone (FL), and tetracyano-p-quinodimethane (TCNQ), is studied in acetonitrile and in micellar aqueous solution of ..
  55. Wurche F, Sicking W, Sustmann R, Klärner F, Rüchardt C. The effect of pressure on hydrogen transfer reactions with quinones. Chemistry. 2004;10:2707-21 pubmed
    ..effect of pressure on the oxidation of hydroarenes 3-9 with 2,3-dichloro-5,6-dicyano-1,4-quinone (DDQ; 1 a) or o-chloranil (10), leading to the corresponding arenes, has been investigated...
  56. Los Weinert P, Pezza H, de Oliveira J, Pezza L. A simplified spectrophotometric method for routine analysis of saccharin in commercial noncaloric sweeteners. J Agric Food Chem. 2004;52:7788-92 pubmed
    ..This method is based on the reaction of saccharin with tetrachloro-p-benzoquinone (p-chloranil) accelerated by hydrogen peroxide and conducted in an ethanol:acetone (4:1) medium, producing a violet-red ..
  57. Datta K, Roy D, Mukherjee A. Spectroscopic and thermodynamic study of charge transfer interaction between vitamin B6 and p-chloranil in aqueous ethanol mixtures of varying composition. Spectrochim Acta A Mol Biomol Spectrosc. 2008;70:425-9 pubmed publisher
    ..found to form between vitamin B(6) (pyridoxine hydrochloride) and a series of electron acceptors including p-chloranil. Since vitamin B(6) is soluble in water while the electron acceptors are insoluble in water but soluble in ..
  58. Hay S, Scrutton N. Incorporation of hydrostatic pressure into models of hydrogen tunneling highlights a role for pressure-modulated promoting vibrations. Biochemistry. 2008;47:9880-7 pubmed publisher
    ..The KIE expression is tested on two data sets {the reduction of chloranil by leuco crystal violet [Isaacs, N. S., Javaid, K., and Rannala, E. (1998) J. Chem. Soc., Perkin Trans...
  59. Tsai C, Lin P, Waidyanatha S, Rappaport S. Characterization of metabolic activation of pentachlorophenol to quinones and semiquinones in rodent liver. Chem Biol Interact. 2001;134:55-71 pubmed
    ..This implies that, under conditions of oxidative stress, endogenous lipid hydroperoxides may increase PCP metabolism sufficiently to enhance the toxicity and carcinogenicity of PCP. ..
  60. Raza A, Ansari T. Spectrophotometric determination of citalopram hydrobromide in tablet dosage form using chloranil. Pak J Pharm Sci. 2014;27:255-60 pubmed
    ..The newly proposed method is based on the charge transfer reaction between citalopram as electron donor and chloranil as electron acceptor. The charge transfer complex of citalopram and chloranil shows ?(max) at 550 nm in methanol...
  61. Noel G, STEVENSON S, Moukhles H. A high throughput screen identifies chemical modulators of the laminin-induced clustering of dystroglycan and aquaporin-4 in primary astrocytes. PLoS ONE. 2011;6:e17559 pubmed publisher
    ..Detailed analysis of the inhibitory drug, chloranil, revealed that its inhibition of the clustering is due to the metalloproteinase-2-mediated ß-dystroglycan ..
  62. Refat M, El Korashy S, El Deen I, El Sayed S. Experimental and spectroscopic studies of charge transfer reaction between sulfasalazine antibiotic drug with different types of acceptors. Drug Test Anal. 2011;3:116-31 pubmed publisher
    ..the electron donor sulfasalazine (SS) and the acceptors 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ), p-chloranil (CHL), picric acid (PA) and iodine have been studied spectrophotometrically in CHCl(3) or CH(3) OH solutions...
  63. Fakhroo A, Bazzi H, Mostafa A, Shahada L. Synthesis, spectroscopic and thermal structural investigations of the charge-transfer complexes formed in the reaction of 1-methylpiperidine with sigma- and pi-acceptors. Spectrochim Acta A Mol Biomol Spectrosc. 2010;75:134-41 pubmed publisher
    ..tetracyanoethylene (TCNE), 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ), 2,3,5,6-tetrachloro-1,4-benzoquinone (chloranil=CHL) and iodine (I(2)) were studied spectrophotometrically in chloroform at room temperature...
  64. Yamamoto Y, Itonaga K. Versatile Friedel-Crafts-type alkylation of benzene derivatives using a molybdenum complex/ortho-chloranil catalytic system. Chemistry. 2008;14:10705-15 pubmed publisher
    ..alkylation reactions of benzene derivatives with alkenes and alcohols in the presence of an organic oxidant, o-chloranil. The utilization of [Mo(CO)(6)] and two equivalents of o-chloranil catalytically furnished the hydroarylation ..
  65. Abdollahi H, Bagheri L. Simultaneous spectrophotometric determination of p-benzoquinone and chloranil after microcrystalline naphthalene extraction by using genetic algorithm-based wavelength selection-partial least squares regression. Anal Sci. 2004;20:1701-6 pubmed
    ..naphthalene extraction has been used for the preconcentration of p-benzoquinone and tetrachloro-p-benzoquinone (chloranil), after their reaction by aniline, and later simultaneous spectrophotometric analysis by genetic algorithm-..
  66. Pandey R, Ghosh S, Mukhopadhyay S, Ramasesha S, Das P. Geometry and quadratic nonlinearity of charge transfer complexes in solution using depolarized hyper-Rayleigh scattering. J Chem Phys. 2011;134:044533 pubmed publisher
    ..All the CT complexes between methyl benzenes and chloranil or 1,2-dichloro-4,5-dicyano-p-benzoquinone investigated here are found to have a slipped parallel stacking of ..
  67. Christl M, Braun M, Deeg O. Photochemical reactions of tetrachloro-1,4-benzoquinone (chloranil) with tricyclo[,7)]heptane (Moore's hydrocarbon) and bicyclo[4.1.0]hept-2-ene (2-norcarene). Org Biomol Chem. 2013;11:2811-7 pubmed publisher
    Solutions of chloranil (CA) in benzene were irradiated in the presence of Moore's hydrocarbon (MH) and 2-norcarene (NC)...
  68. Gorner H, von Sonntag C. Photoprocesses of chloro-substituted p-benzoquinones. J Phys Chem A. 2008;112:10257-63 pubmed publisher
    ..Other mechanisms involving (*)QH/Q (*-) radicals, such as quenching of the triplet state at enhanced Cl n BQ concentrations and H-atom abstraction from an organic solvent in mixtures with water, have also to be considered. ..
  69. Pavan Kumar K, Kumara Swamy K. The first structural study on a cyclic tricoordinate phosphorochloridite and a pentacoordinate phosphorane based on 1,2,3,5-protected myo-inositol--a new conformation of 1,3,2-dioxaphosphorinane ring. Carbohydr Res. 2007;342:1182-8 pubmed
    Treatment of the phosphoramidite [myo-C(6)H(6)-2-[OC(O)Ph]-1,3,5-(O(3)CH)-4,6-(O(2)P-NH-i-Pr)] with o-chloranil affords the first example of inositol-based pentacoordinate phosphorane [myo-C(6)H(6)-2-[OC(O)Ph]-1,3,5-(O(3)CH)-4,6-(O(2)P-..
  70. Bekele T, Shah M, Wolfer J, Abraham C, Weatherwax A, Lectka T. Catalytic, enantioselective [4 + 2]-cycloadditions of ketene enolates and o-quinones: efficient entry to chiral, alpha-oxygenated carboxylic acid derivatives. J Am Chem Soc. 2006;128:1810-1 pubmed
    ..The resulting chiral, bicycloadducts can be synthetically manipulated in a variety of useful ways, for example to provide a flexible synthesis of alpha-oxygenated carboxylic acid derivatives. ..
  71. Nguyen T, Bertagnolli A, Villalta P, Buhlmann P, Sturla S. Characterization of a deoxyguanosine adduct of tetrachlorobenzoquinone: dichlorobenzoquinone-1,N2-etheno-2'-deoxyguanosine. Chem Res Toxicol. 2005;18:1770-6 pubmed
  72. Ray A, Bhattacharya S, Banerjee M, Mukherjee A. Spectrophotometric study of molecular complex formation between o-chloranil and a series of methylated pyridines. Spectrochim Acta A Mol Biomol Spectrosc. 2002;58:1375-8 pubmed
    o-Chloranil has been shown to form 1:1 molecular complexes with pyridine and 2-, 3- and 4-picolines in CCl4 medium. Isosbestic points have been found but charge-transfer bands could not be detected...