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The Isotoluenes in 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....
 are the non-aromatic toluene
Toluene

Toluene, also known as methylbenzene or phenylmethane, is a clear, Water -insoluble liquid with the typical smell of paint thinners, redolent of the sweet smell of the related compound benzene....
 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 with an exocyclic double bond. They are of some academic interest in relation to aromaticity
Aromaticity

Aromaticity is a chemical property in which a conjugated system ring of unsaturated bonds, lone pairs, or empty orbitals exhibit a stabilization stronger than would be expected by the stabilization of conjugation alone....
 and isomerization mechanisms

The three basic isotoluenes are ortho-isotoluene or 5-methylene-1,3-cyclohexadiene. 1, para-isotoluene 2 and meta-isotoluene 3. One more isomer is the bicyclic compound 5-methylenebicyclo[2.2.0] hexene 4.

The o- and p-isotoluenes easily isomerize to toluene
Toluene

Toluene, also known as methylbenzene or phenylmethane, is a clear, Water -insoluble liquid with the typical smell of paint thinners, redolent of the sweet smell of the related compound benzene....
, a reaction driven by aromatic stabilization.






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The Isotoluenes in 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....
 are the non-aromatic toluene
Toluene

Toluene, also known as methylbenzene or phenylmethane, is a clear, Water -insoluble liquid with the typical smell of paint thinners, redolent of the sweet smell of the related compound benzene....
 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 with an exocyclic double bond. They are of some academic interest in relation to aromaticity
Aromaticity

Aromaticity is a chemical property in which a conjugated system ring of unsaturated bonds, lone pairs, or empty orbitals exhibit a stabilization stronger than would be expected by the stabilization of conjugation alone....
 and isomerization mechanisms

The three basic isotoluenes are ortho-isotoluene or 5-methylene-1,3-cyclohexadiene. 1, para-isotoluene 2 and meta-isotoluene 3. One more isomer is the bicyclic compound 5-methylenebicyclo[2.2.0] hexene 4.

The o- and p-isotoluenes easily isomerize to toluene
Toluene

Toluene, also known as methylbenzene or phenylmethane, is a clear, Water -insoluble liquid with the typical smell of paint thinners, redolent of the sweet smell of the related compound benzene....
, a reaction driven by aromatic stabilization. It is estimated that these compounds are 23 kcal/mol less stable.

The isomerization of p-isotoluene to toluene takes place at 100 °C in benzene
Benzene

Benzene, or benzol, is an organic compound chemical compound and a known carcinogen with the molecular formula Carbon6Hydrogen6....
 with bimolecular reaction kinetics by an intermolecular free radical reaction
Free radical reaction

A free radical reaction is any chemical reaction involving free radicals. This reaction type is abundant in organic reactions.Two pioneering studies into free radical reactions have been the discovery of the triphenylmethyl radical by Moses Gomberg and the lead-mirror experiment described by Friedrich Paneth in 1927....
. Other dimer
Dimer

File:Carboxylic acid dimers.pngA dimer is a chemical or biological entity consisting of two identical subunits called monomers, which are held together by either intramolecular forces or weaker intermolecular forces....
 radical reaction products are formed as well.

The ortho isomer is found to isomerize at 60°C also in a second order reaction in benzene. The proposed reaction mechanism
Reaction mechanism

In chemistry, a reaction mechanism is the step by step sequence of elementary reactions by which overall chemical change occurs .Although only the net chemical change is directly observation for most chemical reactions, experiments can often be designed that suggest the possible sequence of steps in a reaction mechanism....
 is a concerted
Concerted reaction

In chemistry, a concerted reaction is a chemical reaction in which all bond breaking and bond making occurs in a single step. Reactive intermediates or other unstable high energy intermediates are not involved....
 intermolecular ene reaction
Ene reaction

The Ene reaction is a chemical reaction between an alkene with an allylic hydrogen and a multiple bond . It is a group transfer reaction. The product is a substituted alkene with the double bond shifted to the allylic position....
. The reaction product is either toluene or a mixture of dimerized ene reaction
Ene reaction

The Ene reaction is a chemical reaction between an alkene with an allylic hydrogen and a multiple bond . It is a group transfer reaction. The product is a substituted alkene with the double bond shifted to the allylic position....
 products depending on the exact reaction conditions. Ortho isotoluene has been researched in connection with the mechanism of initiator
Radical initiator

In chemistry, radical initiators are substances that can produce radical under mild conditions and promote radical polymerization reactions. These substances generally possess weak bonds—bonds that have small bond dissociation energy....
-free polymerization
Polymerization

In polymer chemistry, polymerization is a process of reacting monomer molecules together in a chemical reaction to form three-dimensional networks or polymer chains....
 of polystyrene
Polystyrene

Polystyrene , sometimes abbreviated PS, is an Aromaticity polymer made from the aromatic monomer styrene, a liquid hydrocarbon that is commercially manufactured from petroleum by the chemical industry....
.

See also

  • Pentacene
    Pentacene

    Pentacene is a polycyclic aromatic hydrocarbon consisting of 5 linearly-fused benzene rings. This extended conjugation, together with a favorable crystal structure is responsible for its properties as an organic semiconductor....