Inherent chirality

In chemistry, inherent chirality is a property of asymmetry in molecules arising, not from a stereogenic or chiral center, but from a twisting of the molecule in 3-D space. The term was first coined by Volker Boehmer in a 1994 review, to describe the chirality of calixarenes arising from their non-planar structure in 3-D space.

This phenomenon was described as resulting from "the absence of a place of symmetry or an inversion center in the molecule as a whole". Boehmer further explains this phenomenon by suggesting that if an inherently chiral calixarene macrocycle were opened up it would produce an "achiral linear molecule". There are two commonly used notations to describe a molecules inherent chirality: cR/cS (arising from the notation used for classically chiral compounds, with c denoting curvature) and P/M. Inherently chiral molecules, like their classically chiral counterparts, can be used in chiral host–guest chemistry, enantioselective synthesis, and other applications. There are naturally occurring inherently chiral molecules as well. Retinal, a chromophore in rhodopsin. exists in solution as a racemic pair of enantiomers due to the curvature of an achiral polyene chain.