Arene substitution patterns

Arene Substitution Patterns

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Arene substitution patterns

Arene substitution patterns are part of organic chemistry

Organic chemistry

Organic chemistry is a discipline within chemistry which involves the science study of the structure, properties, composition, chemical reaction, and preparation of chemical compounds that contain carbon....
IUPAC nomenclature

IUPAC nomenclature

IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. It is developed and kept up to date under the auspices of the International Union of Pure and Applied Chemistry ....
and pinpoint the position of substituent

Substituent

In organic chemistry, a substituent is an atom or group of atoms substituted in place of a hydrogen atom on the parent chain of a hydrocarbon. The suffix -yl is used when naming organic compounds that contain a substituent....
s other than hydrogen

Hydrogen

Hydrogen is the chemical element with atomic number 1. It is represented by the chemical symbol H. At standard temperature and pressure, hydrogen is a colorless, odorless, nonmetallic, tasteless, highly combustion and explosive Diatomic molecule gas with the molecular formula H2....
in relation to each other on an aromatic hydrocarbon

Aromatic hydrocarbon

An aromatic hydrocarbon or arene is a hydrocarbon, of which the molecular structure incorporates one or more planar sets of six carbon atoms that are connected by delocalised electrons numbering the same as if they consisted of alternating single and double covalent bonds....
.

Cine and tele substitution

prefixes ortho, meta, and para are all derived from Greek, meaning straight or correct, following or after, and akin to or similar, respectively.

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Encyclopedia

Arene substitution patterns are part of organic chemistry

Organic chemistry

IUPAC nomenclature

Substituent

Hydrogen

Aromatic hydrocarbon

Ortho, meta, and para substitution

In ortho-substitution, two substituents occupy positions next to each other, which may be numbered 1 and 2. In the diagram, these positions are marked R and ortho.
In meta-substitution the substituents occupy positions 1 and 3 (corresponding to R and meta in the diagram).
In para-substitution, the substituents occupy the opposite ends (positions 1 and 4). The toluidine
Toluidine

There are three isomers of toluidine, which are organic compounds. These isomers are o-toluidine, m-toluidine, and p-toluidine....
s serve as an example for these three types of substitution.

Ipso, meso, and peri substitution

Ipso-substitution describes two substituents sharing the same ring position in an intermediate compound in an electrophilic aromatic substitution
Electrophilic aromatic substitution

Electrophilic aromatic substitution or EAS is an organic reaction in which an atom, usually hydrogen, appended to an aromatic ring is replaced by an electrophile....
.
Meso-substitution refers to the substituents occupying a benzyl
Benzyl

In organic chemistry, benzyl is the term used to describe the substituent or molecular fragment possessing the structure C6H5CH2-....
ic position. It is observed in compounds such as calixarene
Calixarene

A calixarene is a macrocycle or Cyclic compound oligomer based on a hydroxyalkylation product of a phenol and an aldehyde [1]. The word calixarene is derived from calix or Chalice because this type of molecule resembles a vase and from the word arene that refers to the aromatic building block....
s and acridine
Acridine

Acridine, C13H9N, is an organic compound and a heterocyclic compound. Acridine is also used to describe compounds containing the C13N tricycle....
s.
Peri-substitution occurs in naphthalene
Naphthalene

Naphthalene, also known as naphthalin, naphthaline, tar camphor, white tar, albocarbon, or antimite and not to be confused with naphtha, is a crystalline, Aromaticity, white, solid hydrocarbon with formula Carbon10hydrogen8 and the structure of two fused benzene rings....
s for substituents at the 1 and 8 positions.

Cine and tele substitution

In cine-substitution, the entering group takes up a position adjacent to that occupied by the leaving group
Leaving group

A leaving group in chemistry is an ion or substituent with the ability to detach itself from a molecule. The remaining molecule or fragment remaining is known as the residual or main part....
. For example, cine-substitution is observed in aryne
Aryne

In chemistry, an aryne is an uncharged reactive intermediate derived from an aromatic ring by removal of two ortho- substituents, leaving two atomic orbital with two electrons distributed between them.....
chemistry.
Tele-substitution occurs when the new position is more than one atom away on the ring.

Origins

The prefixes ortho, meta, and para are all derived from Greek, meaning straight or correct, following or after, and akin to or similar, respectively. The relationship to the current meaning is perhaps not obvious. The ortho description was historically used to designate the original compound, and an isomer was often called the meta compound. For instance, the trivial names orthophosphoric acid

Phosphoric acids and Phosphates

This article compares various kinds of phosphoric acids and phosphates....
and trimetaphosphoric acid have nothing to do with aromatics at all. Likewise, the description para was reserved for just closely-related compounds. Thus Berzelius

Jöns Jakob Berzelius

Friherre J?ns Jacob Berzelius was a Sweden chemist. He worked out the modern technique of chemical formula, and is together with John Dalton, Antoine Lavoisier, and Robert Boyle considered a father of modern chemistry....
originally called the racemic

Racemic

In chemistry, a racemic mixture, or racemate, is one that has equal Amount of substance of left- and right-handed enantiomer of a Chirality molecule....
form of aspartic acid

Aspartic acid

Aspartic acid is an a-amino acid with the chemical formula HO2CCHCH2CO2H. The carboxylate anion of aspartic acid is known as aspartate....
paraaspartic acid (another obsolete term: racemic acid

Racemic acid

Racemic acid is an old name for an optically inactive or racemic form of tartaric acid. It is an equal mixture of two mirror-image isomers , optically active in opposing directions....
) in 1830. The use of the descriptions ortho, meta and para for multiple substituted aromatic rings starts with Wilhelm Körner in the period 1866–1874 although he chose to reserve the ortho prefix for the 1,4 isomer and the meta prefix for the 1,2-isomer. The current nomenclature (different again from that of Körner) was introduced by the Chemical Society

Chemical Society

The Chemical Society was formed in 1841 as a result of increased interest in scientific matters.One of its aims was to hold meetings for "the communication and discussion of discoveries and observations, an account of which shall be published by the Society"....
in 1879 .

Examples

Examples of the use of this nomenclature are given for isomer

Isomer

In chemistry, isomers are compounds with the same molecular formula but different structural formulae. Isomers do not necessarily share similar properties unless they also have the same functional groups....
s of cresol

Cresol

Cresols are organic compounds which are methyl groupphenols. They are a widely occurring natural and manufactured group of aromatic organic compounds which are categorized as phenols ....
:

Catechol, resorcinol

Resorcinol

Resorcinol is a chemical compound from the dihydroxy phenols. It is the 1,3-isomer of benzenediol, and is also known with a variety of other names, including: m-dihydroxybenzene, 1,3-benzenediol, 1,3-dihydroxybenzene, 3-hydroxyphenol, m-hydroquinone, m-benzenediol, and 3-hydroxycyclohexadien-1-one....
and hydroquinone

Hydroquinone

Hydroquinone, also benzene-1,4-diol or quinol, is an aromatic organic compound which is a type of Phenols, having the chemical formula C6H42....
are isomers also:

Phthalic acid

Phthalic acid is an aromatic dicarboxylic acid, with formula C6H42. It is an isomer of isophthalic acid and terephthalic acid....
has two isomers, the meta isomer isophthalic acid

Isophthalic acid

Isophthalic acid is an organic compound with the chemical formula C6H42. This colourless solid is an isomer of phthalic acid and terephthalic acid....
and the para isomer terephthalic acid

Terephthalic acid

Terephthalic acid is the organic compound and one of three isomeric phthalic acids, all with chemical formula C6H42....
: