Electrostatic interactions are responsible for much of the fascinating conformational behavior of saturated heterocyclic compounds. In this connection, the conformational preferences in a series of 2,2-diaryl-1,3-dioxanes and 5-aryl-1,3-dioxanes have been investigated. Remote substituents were varied on the aryl rings and were found to have a profound effect on the conformational equilibria in such systems. In the 5-aryl systems, what was thought to be a seemingly weak CH---O interaction has allowed for the precise “tuning” of the conformational equilibria based on the electron-withdrawing or donating ability of the aryl ring. The importance of these interactions and their application to other small molecule systems will be discussed.

Tuning the conformational equilibria in saturated heterocycles through the manipulation of a non-classical CH---O hydrogen bond: The importance of electrostatic interactions within small molecules

253rd National Meeting (2017)

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