The heat of reaction between sodium methoxide and 2,4,6-trinitroanisole to give sodium 1,ldimethoxy-2,4,6-trinitrocyclohexadienide has been measured in methanolic dimethyl sulfoxide solutions and was found to be 15 kcal/mol more exothermic in 95 DMSO than in methanol. Heats of transfer of sodium methoxide, the Meisenheimer complex, sodium picrate, and 2,4,6-trinitroanisole from methanol to methanolic dimethyl sulfoxide solutions have been measured. The Meisenheimer complex is stabilized much more in DMSO than is the picrate anion. The transfer of sodium methoxide to DMSO rich solvents is endothermic and is a linear function of the H-acidity function.here has been considerable recent interest in the
The heat of formation of the Meisenheimer complex formed from sodium thiophenoxide and 1,3,5-trinitrobenzene has been measured in methanol-DMSO mixtures. These data were combined with free energies from the literature to calculate AS for this reaction. Except at very high DMSO concentrations, this reaction is isoentropic across the methanol-DMSO solvent continuum. The heats of transfer of the starting materials and product from methanol to methanol-DMSO mixtures have been measured. The heat of reaction between thiophenoxide and 1,3,5-trinitrobenzene becomes more exothermic as the concentration of DMSO increases.
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