Abstract
The partial molar volumes (V) and the enthalpies of dissolution (Δdis H) for tetracyanoethylene, cyclopentadiene, and their Diels—Alder adduct were determined at 25°C. Eleven solvents of the π- and n-donor type were used. The use of alkylbenzenes as solvents for tetracyanoethylene induces pronounced changes in the enthalpy of dissolution (up to 26 kJ mol−1) and in the partial molar volume (up to 11 cm3 mol−1), whereas these parameters for the adduct change slightly. TheV and Δdis H values for cyclopentadiene virtually do not depend on the nature of the solvent. In the case of tetracyanoethylene and the adduct in n-donor solvents, considerable variations of theV and Δdis H values are observed; they are not linear functions of the change in the partial molar volume of the adduct. Therefore, the reaction volumes in acetonitrile (−40.69) and ethyl acetate (−45.56) differ sharply from those ino-xylene (−24.28) and mesitylene (−21.76 cm3 mol−1).
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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 6, pp. 1046–1050, June, 2000.
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Kiselev, V.D., Kashaeva, E.A., Shihab, M.S. et al. Dramatic solvent effect on the volume of the Diels-Alder reaction between tetracyanoethylene and cyclopentadiene. Russ Chem Bull 49, 1040–1044 (2000). https://doi.org/10.1007/BF02494892
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DOI: https://doi.org/10.1007/BF02494892