engleski

Gas Phase Acidity of 1-Phenylcyclobutene

As a part of our recent interest in acidity of cyclobutene derivatives and their relevance to assessment of antiaromatic destabilization of cyclobutadiene moiety we report here on acidity determination of 1-phenylcyclobutene (1). It is found that deprotonation of 1 proceeds at the C-3 position giving rise to the 1-phenylallyl type anion 2. Gas phase energetic data (DeltaH_a, EA and C-H BDE) as obtained by the bracketing technique and a thermodynamic cycle will be presented and compared with the previously published results for the parent cyclobutene ring. Effect of phenyl ring on the stability of anion 2, based on the results of high level ab initio calculations, will be discussed.

acidity; phenylcyclobutene; antiaromatic destabilization

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