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Planar chirality

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Through Dimension, Mathematics and Chemistry

Most fundamentally, planar chirality is a mathematical term, finding use in chemistry, physics and related physical sciences, for example, in astronomy, optics and metamaterials. Recent occurrences in latter two fields are dominated by microwave and terahertz applications as well as micro- and nanostructured planar interfaces for infrared and visible light.

In chemistry

This term is used in chemistry describe molecules that are chiral despite lacking an asymmetric carbon atom. In these cases, chirality results from the arrangement of groups extending out of a reference plane (chirality plane), which makes the molecule and its mirror image non-superposable. Examples include (E)-cyclooctene, some di- or poly-substituted metallocenes, and certain monosubstituted paracyclophanes. Nature rarely provides planar chiral molecules, cavicularin being an exception.

Assigning the configuration of planar chiral molecules

To assign the configuration of a planar chiral molecule, begin by selecting the pilot atom, which is the highest priority of the atoms that is not in the plane, but is directly attached to an atom in the plane. Next, assign the priority of the three adjacent in-plane atoms, starting with the atom attached to the pilot atom as priority 1, and preferentially assigning in order of highest priority if there is a choice. Then set the pilot atom to in front of the three atoms in question. If the three atoms reside in a clockwise direction when followed in order of priority, the molecule is assigned as R; when counterclockwise it is assigned as S.

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