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The chirality of a molecule that has a helical, propeller, or screw-shaped geometry is called helicity [5] or helical chirality. [6] [7] The screw axis or the D n, or C n principle symmetry axis is considered to be the axis of chirality. Some sources consider helical chirality to be a type of axial chirality, [7] and some do not.
These types of chirality are far less common than central chirality. BINOL is a typical example of an axially chiral molecule, while trans-cyclooctene is a commonly cited example of a planar chiral molecule. Finally, helicene possesses helical chirality, which is one type of inherent chirality.
Atropisomers exhibit axial chirality (planar chirality). When the barrier to racemization is high, as illustrated by the BINAP ligands, the phenomenon becomes of practical value in asymmetric synthesis. Methaqualone, the anxiolytic and hypnotic-sedative, is a classical example of a drug molecule that exhibits the phenomenon of atropisomerism. [9]
Macroscopic examples of chirality are found in the plant kingdom, the animal kingdom and all other groups of organisms. A simple example is the coiling direction of any climber plant, which can grow to form either a left- or right-handed helix. In anatomy, chirality is found in the imperfect mirror image symmetry of many kinds of animal bodies.
The chiral symmetry transformation can be divided into a component that treats the left-handed and the right-handed parts equally, known as vector symmetry, and a component that actually treats them differently, known as axial symmetry. [2] (cf. Current algebra.) A scalar field model encoding chiral symmetry and its breaking is the chiral model.
[5]: 1138ff First, while nevertheless appearing to be twisted, they yet may have a chiral center making them analogous to any simple chiral compound, and second, while again appearing twisted, the specific location of substituents, as with alkylidenecycloalkanes, may make a spiro compound display central chirality (rather than axial chirality ...
This chiral diphosphine ligand is widely used in asymmetric synthesis. It consists of a pair of 2-diphenylphosphinonaphthyl groups linked at the 1 and 1′ positions. This C 2-symmetric framework lacks a stereogenic atom, but has axial chirality due to restricted rotation (atropisomerism).
Planar chirality, also known as 2D chirality, is the special case of chirality for two dimensions. Most fundamentally, planar chirality is a mathematical term, finding use in chemistry , physics and related physical sciences, for example, in astronomy , optics and metamaterials .