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Spectrophotometric Investigation of the Charge–Transfer Interaction of 2,3-Dicyano-1,4-naphthoquinone with N-Ethylaniline in Chlorinated Solvents

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Abstract

The charge–transfer interaction between 2,3-dicyano-1,4-naphthoquinone (DCNQ) and N-ethylaniline was studied in the halocarbons chloroform and dichloromethane and a 1:1 (v/v) mixture of these two solvents. A rapid interaction between DCNQ and N-ethylaniline results in the formation of the monosubstituted final product. The reaction is found to proceed through an initial charge–transfer (CT) complex intermediate. The equilibrium constants of the π-complex, in all the three media, were evaluated along with first-order and second-order rate constants for the appearance and disappearance of the π- and σ-complexes. The final product was isolated and characterized by IR, NMR and elemental analysis. Based on the kinetic results a mechanism was proposed for the reaction.

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Author notes

  1. Subhash R. Magadum

    Present address: Dept. of Chemistry, S.B. Arts & K.C.P. Science College, Bijapur, 586103, Karnataka, India

Authors and Affiliations

  1. P.G. Department of Studies in Chemistry, Karnatak University, Dharwad, 580003, India

    Subhash R. Magadum, Gururaj M. Neelgund, Abhay S. Kulkarni & M. L. Budni

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  1. Subhash R. Magadum
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  2. Gururaj M. Neelgund
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Magadum, S.R., Neelgund, G.M., Kulkarni, A.S. et al. Spectrophotometric Investigation of the Charge–Transfer Interaction of 2,3-Dicyano-1,4-naphthoquinone with N-Ethylaniline in Chlorinated Solvents. J Solution Chem 41, 1067–1078 (2012). https://doi.org/10.1007/s10953-012-9852-1

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