Introduction of a double bond in to cyclopropane has two effects, the overall ring strain is increased by a factor of two and two sets of potential carbon-acid sites now exist (vinyl and allylic). It has been shown experimentally that the vinyl hydrogen of cyclopropene derivatives show enhanced acidity compared to cyclopropane's hydrogen or cyclopropene's own allylic hydrogen. Experimental substituent effects on cyclopropene's acidity are of the expected type. Alkyl groups are strongly destabilizing while phenyl groups provide moderate stabilization. What is unknown is the effect of fluorine on the acidity of cyclopropenes and the cyclopropenyl anion. Fluorine as a substituent has resulted in some unusual chemistry. The term �schizoid� has been used often to describe the chemistry of the fluoro substituents due to its pi-donating and sigma-withdrawing character. Continued ab initio and DFT study of the stabilization and destabilization effect fluorine has on pi and sigma systems of cyclopropenes will be explored and presented here. The effect fluorine has on strained systems makes this of particular interest to both experimental and theoretical chemists.

Computational study of the fluoro-substituent effect on cyclopropene acidity and anion structure

247th National Meeting (2014)

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