Introduction of a double bond in to cyclopropene has two effects, the overall ring strain is increased and two sets of potential carbon-acid sites now exist. 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. What is unknown is the effect of fluorine on the acidity of cyclopropenes and the cyclopropenyl anion. 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.

Computational study of the fluoro-substituent effect on cyclopropane acidity

251st National Meeting (2016)

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