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Ring strain is an 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....
 term that describes the destabilization of a cyclic molecule
Molecule

In chemistry, a molecule is defined as a sufficiently stable, electric charge neutral group of at least two atoms in a definite arrangement held together by very strong chemical bonds....
—such as a cycloalkane
Cycloalkane

Cycloalkanes are types of alkanes which have one or more rings of carbon atoms in the chemical structure of their molecules. Alkanes are types of Organic compound hydrocarbon Chemical compound which have only single chemical bonds in their chemical structure....
—due to the non-favorable high energy
Energy

In physics, energy is a scalar physical quantity that describes the amount of Work_ that can be performed by a force. Energy is an attribute of objects and systems that is subject to a conservation law....
 spatial orientations
Molecular geometry

Molecular geometry or molecular structure is the three-dimensional arrangement of the atoms that constitute a molecule. It determines several properties of a substance including its Reactivity , Chemical polarity, Phase , color, magnetism, and biological activity....
 of its atoms. Non-cyclic molecules do not exhibit ring strain because their terminal (end) atoms are not connected to force a particular type of spatial orientation.

Ring strain results from a combination of angle strain
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....
, conformational strain or Pitzer strain, and transannular strain or van der Waals strain
Van der Waals strain

In chemistry, van der Waals strain is strain resulting from van der Waals force repulsion when two substituents in a molecule approach each other with a distance less than the sum of their Van der Waals radius....
.

cules with a high amount of ring strain
Ring strain

Ring strain is an organic chemistry term that describes the destabilization of a cyclic molecule?such as a cycloalkane?due to the non-favorable high energy Molecular geometry of its atoms....
 consist of three, four, and some five-membered rings, including: cyclopropanes, cyclopropene
Cyclopropene

Cyclopropene is an organic compound with the chemical formula 34. It is the simplest isolable cycloalkene. It has a triangle structure....
s, cyclobutanes, cyclobutene
Cyclobutene

Cyclobutene is a cycloalkene with chemical formula 46 and CAS number 822-35-5. It is used in chemical industry as a monomer for synthesis of some polymers and for a range of chemical syntheses....
s, [1,1,1]propellane
Propellane

Propellanes are a class of bicyclic molecule organic compounds sharing a common carbon-carbon bond. They are characterized by the presence of carbon with an inverted tetrahedral geometry, large steric strain and high reactivity and are for these reasons much studied in organic chemistry....
s, [2,2,2]propellane
Propellane

Propellanes are a class of bicyclic molecule organic compounds sharing a common carbon-carbon bond. They are characterized by the presence of carbon with an inverted tetrahedral geometry, large steric strain and high reactivity and are for these reasons much studied in organic chemistry....
s, epoxides, aziridines, cyclopentene
Cyclopentene

Cyclopentene is a chemical compound with the formula 58. It is a colorless liquid with a petrol-like odor. It is one of the cycloalkenes....
s, and norbornene
Norbornene

Norbornene or norbornylene or norcamphene is a bridged cyclic hydrocarbon. It is a white solid with a pungent sour odor. The molecule consists of a cyclohexene ring bridged with a methylene group in the arene substitution patterns....
s.






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Encyclopedia


Ring strain is an 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....
 term that describes the destabilization of a cyclic molecule
Molecule

In chemistry, a molecule is defined as a sufficiently stable, electric charge neutral group of at least two atoms in a definite arrangement held together by very strong chemical bonds....
—such as a cycloalkane
Cycloalkane

Cycloalkanes are types of alkanes which have one or more rings of carbon atoms in the chemical structure of their molecules. Alkanes are types of Organic compound hydrocarbon Chemical compound which have only single chemical bonds in their chemical structure....
—due to the non-favorable high energy
Energy

In physics, energy is a scalar physical quantity that describes the amount of Work_ that can be performed by a force. Energy is an attribute of objects and systems that is subject to a conservation law....
 spatial orientations
Molecular geometry

Molecular geometry or molecular structure is the three-dimensional arrangement of the atoms that constitute a molecule. It determines several properties of a substance including its Reactivity , Chemical polarity, Phase , color, magnetism, and biological activity....
 of its atoms. Non-cyclic molecules do not exhibit ring strain because their terminal (end) atoms are not connected to force a particular type of spatial orientation.

Ring strain results from a combination of angle strain
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....
, conformational strain or Pitzer strain, and transannular strain or van der Waals strain
Van der Waals strain

In chemistry, van der Waals strain is strain resulting from van der Waals force repulsion when two substituents in a molecule approach each other with a distance less than the sum of their Van der Waals radius....
.

Examples

Molecules with a high amount of ring strain
Ring strain

Ring strain is an organic chemistry term that describes the destabilization of a cyclic molecule?such as a cycloalkane?due to the non-favorable high energy Molecular geometry of its atoms....
 consist of three, four, and some five-membered rings, including: cyclopropanes, cyclopropene
Cyclopropene

Cyclopropene is an organic compound with the chemical formula 34. It is the simplest isolable cycloalkene. It has a triangle structure....
s, cyclobutanes, cyclobutene
Cyclobutene

Cyclobutene is a cycloalkene with chemical formula 46 and CAS number 822-35-5. It is used in chemical industry as a monomer for synthesis of some polymers and for a range of chemical syntheses....
s, [1,1,1]propellane
Propellane

Propellanes are a class of bicyclic molecule organic compounds sharing a common carbon-carbon bond. They are characterized by the presence of carbon with an inverted tetrahedral geometry, large steric strain and high reactivity and are for these reasons much studied in organic chemistry....
s, [2,2,2]propellane
Propellane

Propellanes are a class of bicyclic molecule organic compounds sharing a common carbon-carbon bond. They are characterized by the presence of carbon with an inverted tetrahedral geometry, large steric strain and high reactivity and are for these reasons much studied in organic chemistry....
s, epoxides, aziridines, cyclopentene
Cyclopentene

Cyclopentene is a chemical compound with the formula 58. It is a colorless liquid with a petrol-like odor. It is one of the cycloalkenes....
s, and norbornene
Norbornene

Norbornene or norbornylene or norcamphene is a bridged cyclic hydrocarbon. It is a white solid with a pungent sour odor. The molecule consists of a cyclohexene ring bridged with a methylene group in the arene substitution patterns....
s. These molecules have bond angles between ring atoms which are more acute than the optimal tetrahedral (109.5°) and trigonal planar (120°) bond angles required by their respective sp3 and sp2 bonds. Because of the smaller bond angles, the bonds have higher energy and adopt more p-character to reduce the energy of the bonds. In addition, the ring structures of cyclopropanes/enes and cyclclobutanes/enes offer very little conformational flexibility. Thus, the substituents of ring atoms exist in an eclipsed conformation in cyclopropanes and between gauche and eclipsed in cyclobutanes, contributing to higher ring strain
Ring strain

Ring strain is an organic chemistry term that describes the destabilization of a cyclic molecule?such as a cycloalkane?due to the non-favorable high energy Molecular geometry of its atoms....
 energy in the form of Van der Waals repulsion.

Organic Synthesis

The potential energy and unique bonding structure contained in the bonds of molecules with ring strain can be used to drive reactions in organic synthesis
Organic synthesis

Organic synthesis is a special branch of chemical synthesis and is concerned with the construction of organic compounds via organic reactions. Organic_chemistry molecules can often contain a higher level of complexity compared to purely Inorganic_chemistry compounds, so the synthesis of organic compounds has developed into one of the most im...
. Examples of such reactions are Ring opening metathesis polymerisation
Ring opening metathesis polymerisation

Ring-opening metathesis polymerization is a type of olefin metathesis polymerization that produces industrially important products. The driving force of the reaction is relief of Strain in cyclic olefins and a wide variety of catalysts have been discovered....
, photo-induced ring opening of cyclobutene
Cyclobutene

Cyclobutene is a cycloalkene with chemical formula 46 and CAS number 822-35-5. It is used in chemical industry as a monomer for synthesis of some polymers and for a range of chemical syntheses....
s, and nucleophilic ring-opening of epoxides and aziridines.