This project determines the mechanism of reaction of p-tolyl chlorothionoformate, a compound used in proteomic research. Its solvolysis rates of reaction were first compared to those of the parent phenyl chlorothionoformate. We found that the two solvolysis mechanisms are remarkably similar. Initial results indicate that both compounds favor an addition-elimination reaction in the more nucleophilic solvents. A unimolecular SN1 reaction is favored in the presence of highly ionizing solvents such as 2,2,2,-trifluoroethanol and 1,1,1,3,3,3-hexafluoro-2-propanol. Rates of reaction were calculated using the modified Guggenheim method and the mechanisms were determined by analyzing solvolysis rates using the extended Grunwald-Winstein equation.

Studies of substituent effects in phenyl chlorothionoformate esters

243rd National Meeting (2012)

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