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Cyclobutane
 
 
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Cyclobutane, C4H8, with a molecular mass of 56.107g/mol, is a four carbon
Carbon

Carbon is a chemical element with chemical symbol C and atomic number 6. As a member of group 14 on the periodic table, it is nonmetallic and tetravalence?making four electrons available to form covalent bond chemical bonds....
 alkane
Alkane

Alkanes, also known as paraffins, are chemical compounds that consist only of the elements carbon and hydrogen , wherein these atoms are linked together exclusively by single bonds without any cyclic structure ....
 in which all the carbon
Carbon

Carbon is a chemical element with chemical symbol C and atomic number 6. As a member of group 14 on the periodic table, it is nonmetallic and tetravalence?making four electrons available to form covalent bond chemical bonds....
 atom
Atom

|-! bgcolor=gray | Properties|-||}The atom is a basic unit of matter consisting of a dense, central atomic nucleus surrounded by a electron cloud of electric charge electrons....
s are arranged cyclically, hence cyclobutane. Cyclobutane is a gas and commercially available as a liquefied gas.

Cyclobutanes are cyclobutane derivatives.

90 degree bond angles between carbon
Carbon

Carbon is a chemical element with chemical symbol C and atomic number 6. As a member of group 14 on the periodic table, it is nonmetallic and tetravalence?making four electrons available to form covalent bond chemical bonds....
 atom
Atom

|-! bgcolor=gray | Properties|-||}The atom is a basic unit of matter consisting of a dense, central atomic nucleus surrounded by a electron cloud of electric charge electrons....
s are significantly strained
Angle strain

The presence of angle strain in a molecule indicates that in a specific chemical conformation there exist bond angles that deviate from the ideal bond angles required to achieve maximum bond strength....
 and as such have greater bond energies
Bond energy

In chemistry, bond energy is a measure of bond strength in a chemical bond. For example the carbon-hydrogen bond energy in methane E is the enthalpy change involved with breaking up one molecule of methane into a carbon atom and 4 hydrogen Radical s divided by 4....
 than either linear butane
Butane

Butane, also called n-butane, is the unbranched alkane with four carbon atoms, CH3CH2CH2CH3....
 molecules or larger homocyclic alkanes such as cyclohexane
Cyclohexane

Cyclohexane is a cycloalkane with the molecular formula Carbon6Hydrogen12. Cyclohexane is used as a nonpolar solvent for the chemical industry, and also as a raw material for the industrial production of adipic acid and caprolactam, both of which are intermediates used in the production of nylon....
.






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Cyclobutane, C4H8, with a molecular mass of 56.107g/mol, is a four carbon
Carbon

Carbon is a chemical element with chemical symbol C and atomic number 6. As a member of group 14 on the periodic table, it is nonmetallic and tetravalence?making four electrons available to form covalent bond chemical bonds....
 alkane
Alkane

Alkanes, also known as paraffins, are chemical compounds that consist only of the elements carbon and hydrogen , wherein these atoms are linked together exclusively by single bonds without any cyclic structure ....
 in which all the carbon
Carbon

Carbon is a chemical element with chemical symbol C and atomic number 6. As a member of group 14 on the periodic table, it is nonmetallic and tetravalence?making four electrons available to form covalent bond chemical bonds....
 atom
Atom

|-! bgcolor=gray | Properties|-||}The atom is a basic unit of matter consisting of a dense, central atomic nucleus surrounded by a electron cloud of electric charge electrons....
s are arranged cyclically, hence cyclobutane. Cyclobutane is a gas and commercially available as a liquefied gas.

Cyclobutanes are cyclobutane derivatives.

Conformation

The 90 degree bond angles between carbon
Carbon

Carbon is a chemical element with chemical symbol C and atomic number 6. As a member of group 14 on the periodic table, it is nonmetallic and tetravalence?making four electrons available to form covalent bond chemical bonds....
 atom
Atom

|-! bgcolor=gray | Properties|-||}The atom is a basic unit of matter consisting of a dense, central atomic nucleus surrounded by a electron cloud of electric charge electrons....
s are significantly strained
Angle strain

The presence of angle strain in a molecule indicates that in a specific chemical conformation there exist bond angles that deviate from the ideal bond angles required to achieve maximum bond strength....
 and as such have greater bond energies
Bond energy

In chemistry, bond energy is a measure of bond strength in a chemical bond. For example the carbon-hydrogen bond energy in methane E is the enthalpy change involved with breaking up one molecule of methane into a carbon atom and 4 hydrogen Radical s divided by 4....
 than either linear butane
Butane

Butane, also called n-butane, is the unbranched alkane with four carbon atoms, CH3CH2CH2CH3....
 molecules or larger homocyclic alkanes such as cyclohexane
Cyclohexane

Cyclohexane is a cycloalkane with the molecular formula Carbon6Hydrogen12. Cyclohexane is used as a nonpolar solvent for the chemical industry, and also as a raw material for the industrial production of adipic acid and caprolactam, both of which are intermediates used in the production of nylon....
. As such, cyclobutane is unstable above about 500 °C.

The chemical conformation of cyclobutane is not planar but folded or "puckered". One of the carbon atoms makes a 25° angle with the plane formed by the other three carbons. In this way some of the hydrogen eclipsing interactions are reduced. The conformation is also known as a "butterfly". In substituted cycloalkanes both planar and puckered conformations exist because the energy difference between the two states can be small they can interconvert.

Cyclobutanes in nature

Pentacycloanammoxicacid
Despite inherent strain the cyclobutane motif is not an alien to molecules found in nature. One unusual example is pentacycloanammoxic acid which is a ladderane
Ladderane

A ladderane is an organic molecule containing two or more fused rings of cyclobutane. The name is a portmanteau because the serial cyclobutane rings look like a ladder and are singly bonded like alkanes....
 composed of 5 fused cyclobutane units. The estimated strain in this compound is 3 times that of cyclobutane. The compound is found in bacteria performing the anammox
Anammox

Anammox, an abbreviation for anaerobic ammonium oxidation, is a stage in the nitrogen cycle. In this biological process, nitrite and ammonium are converted directly into dinitrogen gas....
process where it forms part of a tight and very dense membrane believed to protect the organism from toxic hydroxylamine
Hydroxylamine

Hydroxylamine is a reactive chemical with chemical formula NH2OH. It can be considered a hybrid of ammonia and water due to parallels it shares with each....
 and hydrazine
Hydrazine

Hydrazine is a chemical compound with the chemical formula N2H4. It is a colourless liquid with an ammonia-like odor and is derived from the same industrial chemistry processes that manufacture ammonia....
 involved in the production of nitrogen and water from nitrite
Nitrite

The nitrite ion is NO2-. The anion is bent, being isoelectronic with ozone. More generally, a nitrite compound is either a Salt or an ester of nitrous acid....
 ions and ammonia
Ammonia

Ammonia is a chemical compound with the chemical formula nitrogenhydrogen. It is normally encountered as a gas with a characteristic pungent odor....
. Some related fenestrane
Fenestrane

A fenestrane in organic chemistry is a type of chemical compound with a central quaternary carbon atom which serves as a common vertex for four fused compound carbocycles....
s are also found in nature.


External links

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