Passage of Aryl-Tripped Alkyl Groups through Molecular Cavities: The Role of Flexibility

Article abstract of DOI:10.1021/ja00291a036

A series of ω-phenylalkyl esters of cyclophane 2 were synthesized.Cyclophane 2 has a cavity ca. 4.5 Angstroem by 6 Angstroem through which the phenylalkyl groups may pass.The activation energy for passage of the phenylalkyl groups through the cyclophane's cavity varies with structure in a manner which suggests dominant importance of alkyl group flexibility.These conclusions are supported by molecular mechanics calculations.