Strain energy
Encyclopedia
In a molecule
Molecule
A molecule is an electrically neutral group of at least two atoms held together by covalent chemical bonds. Molecules are distinguished from ions by their electrical charge...

, strain energy is released when the constituent atoms are allowed to rearrange themselves in a chemical reaction
Chemical reaction
A chemical reaction is a process that leads to the transformation of one set of chemical substances to another. Chemical reactions can be either spontaneous, requiring no input of energy, or non-spontaneous, typically following the input of some type of energy, such as heat, light or electricity...

 or a change of chemical conformation in a way that:
  • angle strain
    Angle strain
    Angle strain, also called Baeyer strain in cyclic molecules, is the resistance associated with bond angle compression or bond angle expansion. It occurs when bond angles deviate from the ideal bond angles to achieve maximum bond strength in a specific chemical conformation...

    ,
  • torsional strain,
  • ring strain
    Ring strain
    In organic chemistry, ring strain is the tendency of a cyclic molecule, such as cyclopropane, to destabilize when its atoms are in non-favorable high energy spatial orientations...

     and/or steric strain,
  • Allylic strain
    Allylic strain
    thumb | 250 px | right | Allylic strain in an olefin.Allylic strain in organic chemistry is a type of strain energy resulting from the interaction between a substituent on one end of an olefin with an allylic substituent on the other end...

    , and
  • pentane interference
    Pentane interference
    Pentane interference or syn-pentane interaction is the steric hindrance that the two terminal methyl groups experience in one of the chemical conformations of n-pentane...


are reduced. The external work done on an elastic member in causing it to distort from its unstressed state is transformed into strain energy which is a form of potential energy. The strain energy in the form of elastic deformation is mostly recoverable in the form of mechanical work.

For example, the heat of combustion
Heat of combustion
The heat of combustion is the energy released as heat when a compound undergoes complete combustion with oxygen under standard conditions. The chemical reaction is typically a hydrocarbon reacting with oxygen to form carbon dioxide, water and heat...

 of cyclopropane
Cyclopropane
Cyclopropane is a cycloalkane molecule with the molecular formula C3H6, consisting of three carbon atoms linked to each other to form a ring, with each carbon atom bearing two hydrogen atoms...

 (696 kJ/mol) is higher than that of propane
Propane
Propane is a three-carbon alkane with the molecular formula , normally a gas, but compressible to a transportable liquid. A by-product of natural gas processing and petroleum refining, it is commonly used as a fuel for engines, oxy-gas torches, barbecues, portable stoves, and residential central...

 (657 kJ/mol) per methylene
Methylene
Methylene is a chemical species in which a carbon atom is bonded to two hydrogen atoms. Three different possibilities present themselves:* the -CH2- substituent group: e.g., dichloromethane ....

 unit. Compounds with unusually large strain energy include tetrahedrane
Tetrahedrane
Tetrahedrane is a platonic hydrocarbon with chemical formula 44 and a tetrahedral structure. Extreme angle strain prevents this molecule from forming naturally....

s, propellane
Propellane
In organic chemistry, propellane is any member of a class of polycyclic hydrocarbons, whose carbon skeleton consists of three rings of carbon atoms sharing a common carbon-carbon covalent bond...

s, cubane
Cubane
Cubane is a synthetic hydrocarbon molecule that consists of eight carbon atoms arranged at the corners of a cube, with one hydrogen atom attached to each carbon atom. A solid crystalline substance, cubane is one of the Platonic hydrocarbons. It was first synthesized in 1964 by Philip Eaton, a...

s, 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 carbocycles. They can be regarded as spiro compounds twice over. Because of their inherent strain and instability fenestranes are of theoretical...

s and cyclophane
Cyclophane
A cyclophane is a hydrocarbon consisting of an aromatic unit and an aliphatic chain that forms a bridge between two non-adjacent positions of the aromatic ring. More complex derivatives with multiple aromatic units and bridges forming cagelike structures are also known...

s.
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