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Chemistry · L5 · Biaryl Rotational Barrier and Configurational Stability

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How ortho-substituent bulk on a biaryl axis determines the rotational barrier, and how that barrier decides whether the resulting atropisomers are isolable or rapidly interconverting.

by @openstemUpdated Chemistry
Biaryl axis with ortho substituentsRotation passes through planar transition stateSteric clash at transition stateLow rotational barrierHigh rotational barrier greater than 20 kcal per molFast interconversion at room temperatureSlow interconversion: configurationally stable atropisomersResolvable into single enantiomers, e.g. BINOL, BINAPLow clash, small groupsHigh clash, bulky groups

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