Inversion barrier

In chemistry, pyramidal inversion is a fluxional process in compounds with a pyramidal molecule, such as ammonia (NH3) 'turns inside out'. It is a rapid oscillation of the atom and substituents, the molecule or ion passing through a planar transition state. For a compound that would otherwise be chiral due to a stereocenter, pyramidal inversion allows its enantiomers to racemize. In chemistry, pyramidal inversion is a fluxional process in compounds with a pyramidal molecule, such as ammonia (NH3) 'turns inside out'. It is a rapid oscillation of the atom and substituents, the molecule or ion passing through a planar transition state. For a compound that would otherwise be chiral due to a stereocenter, pyramidal inversion allows its enantiomers to racemize. The identity of the inverting atom has a dominating influence on the barrier. Inversion of ammonia is rapid at room temperature. In contrast, phosphine (PH3) inverts very slowly at room temperature (energy barrier: 132 kJ/mol). Consequently, amines of the type RR′R'N are not optically stable (enantiomers racemize rapidly at room temperature), but P-chiral phosphines are. Appropriately substituted sulfonium salts, sulfoxides, arsines, etc. are also optically stable near room temperature. Steric effects can also influence the barrier.