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Chemistry · L5 · Biaryl Rotational Barrier and Configurational Stability

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.

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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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