Concept
Chirality (chemistry)
Overview
In chemistry, a molecule or ion is called chiral () if it cannot be superposed on its mirror image by any combination of rotations, translations, and some conformational changes. This geometric property is called chirality (). The terms are derived from Ancient Greek χείρ (cheir) 'hand'; which is the canonical example of an object with this property.
A chiral molecule or ion exists in two stereoisomers that are mirror images of each other, called enantiomers; they are often distinguished as either "right-handed" or "left-handed" by their absolute configuration or some other criterion. The two enantiomers have the same chemical properties, except when reacting with other chiral compounds. They also have the same physical properties, except that they often have opposite optical activities. A homogeneous mixture of the two enantiomers in equal parts, a racemic mixture, differs chemically and physically from the pure enantiomers.
Chiral molecules will usually have a stereogenic element from which chirality arises. The most common type of stereogenic element is a stereogenic center, or stereocenter. In the case of organic compounds, stereocenters most frequently take the form of a carbon atom with four distinct groups attached to it in a tetrahedral geometry. Less commonly, other atoms like N, P, S, and Si can also serve as stereocenters, provided they have four distinct substituents (including lone pair electrons) attached to them.
A given stereocenter has two possible configurations (R and S), which give rise to stereoisomers (diastereomers and enantiomers) in molecules with one or more stereocenter. For a chiral molecule with one or more stereocenter, the enantiomer corresponds to the stereoisomer in which every stereocenter has the opposite configuration. An organic compound with only one stereogenic carbon is always chiral. On the other hand, an organic compound with multiple stereogenic carbons is typically, but not always, chiral. In particular, if the stereocenters are configured in such a way that the molecule can take a conformation having a plane of symmetry or an inversion point, then the molecule is achiral and is known as a meso compound.
Molecules with chirality arising from one or more stereocenters are classified as possessing central chirality. There are two other types of stereogenic elements that can give rise to chirality, a stereogenic axis (axial chirality) and a stereogenic plane (planar chirality). Finally, the inherent curvature of a molecule can also give rise to chirality (inherent chirality). 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.
Chirality is an important concept for stereochemistry and biochemistry. Most substances relevant to biology are chiral, such as carbohydrates (sugars, starch, and cellulose), all but one of the amino acids that are the building blocks of proteins, and the nucleic acids. Naturally occurring triglycerides are often chiral, but not always. In living organisms, one typically finds only one of the two enantiomers of a chiral compound. For that reason, organisms that consume a chiral compound usually can metabolize only one of its enantiomers. For the same reason, the potencies or effects of enantiomers of a pharmaceutical can differ sharply.
Overview adapted from Wikipedia (CC BY-SA 4.0; see the article history for authors).
Possible passages
Found by search and not yet checked by a person; they may only mention the idea in passing.
Still more strongly will a similar presumption exist, when the object itself, as in the case of organized beings, is no primeval agent, but an effect, which depends on a cause or causes for its very existence. The Kinds, therefore, which are called in chemistry simple substances, or elementary natural agents, are the only ones, any of whose properties can with certainty be considered ultimate; and of these the…
John Stuart Mill, A System of Logic, Ratiocinative and Inductive
States what Chirality is.
And reciprocally: Two sets of four straight lines are defined as having the same anharmonic ratio when (1) each set of four passes through a single point, and (2) corresponding lines of different sets pass, two by two, through four points in one straight line, or when both sets have this relation to any third set. Two sets of points or of lines, which have the same anharmonic ratio, are treated by projective…
Bertrand Russell, An essay on the foundations of geometry
States what Chirality is.
The theory that matter consists of “atoms”, _i.e._ of little bits that cannot be divided, is due to the Greeks, but with them it was only a speculation. The evidence for what is called the atomic theory was derived from chemistry, and the theory itself, in its nineteenth-century form, was mainly due to Dalton. It was found that there were a number of “elements”, and that other substances were compounds of these…
Bertrand Russell, Philosophy
States what Chirality is.
Related ideas
Place in the tradition
Part of Philosophy of chemistry.