Solvent effect on the equilibrium constant of the chain reversible reaction of <Emphasis Type="Italic">N,N</Emphasis>′-diphenyl-1,4-benzoquinonediimine with 2,5-dichlorohydroquinone |
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Authors: | S Ya Gadomsky V T Varlamov |
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Institution: | (1) Institute of Problems of Chemical Physics, Russian Academy of Sciences, 1 prosp. Akad. Semenova, 142432 Chernogolovka, Moscow Region, Russian Federation |
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Abstract: | The temperature dependences of the equilibrium constant K of the reversible chain reaction of N,N′-diphenyl-1,4-benzoquinonediimine with 2,5-dichlorohydroquinone in benzene, chlorobenzene, anisole, benzonitrile, and CCl4 were studied. The enthalpies and entropies of the reaction in these solvents were determined, and a linear dependence between
them in aromatic solvents was found. The equilibrium constant depends on the solvent nature: the replacement of CCl4 by benzene at T = 298 K increases K from 13.6 to 140. The solvation effects are caused by several types of intermolecular interactions of participants of equilibrium
with the medium. The decrease in K in the benzene-anisole-benzonitrile series is related, to a great extent, to complex formation with hydrogen bonding between
2,5-dichlorohydroquinone and the solvents. In anisole a charge-transfer complex is formed between the solvent and reaction
product (2,5-dichloroquinone). The constant and enthalpy of the complexation were estimated.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2296–2302, December, 2007. |
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Keywords: | N N′ -diphenyl-1 4-phenylenediamine 2 5-dichlorohydroquinone N N′ -diphenyl-1 4-benzoquinonediimine 2 5-dichloroquinone reversible chain reactions equilibrium constant reaction enthalpy and entropy hydrogen bonding complexation |
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