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Ring strain
In organic chemistry, ring strain is a type of instability that exists when bonds in a molecule form angles that deviate from their normal values as a result of being part of a ring. This type of strain is most commonly discussed for small rings such as cyclopropanes and cyclobutanes, whose internal angles are substantially smaller than the idealized value of approximately 109°. Because of their high strain, the heat of combustion for these small rings is elevated.
Ring strain results from a combination of angle strain, conformational strain or Pitzer strain (torsional eclipsing interactions), and transannular strain, also known as van der Waals strain or Prelog strain. The simplest examples of angle strain are small cycloalkanes such as cyclopropane and cyclobutane.
Ring strain energy can be attributed to the energy required for the distortion of bond and bond angles in order to close a ring.
The avoidance or reduction of ring strain can help direct or accelerate chemical reactions.
Ring strain theory was first developed by German chemist Adolf von Baeyer in 1890. Previously, the only types of strain believed to exist were torsional and steric; however, Baeyer's theory became based on the interactions between the two strains. Baeyer's theory was based on the assumption that the rings in cyclic compouns compounds were flat, and the simple geometry required for atoms in a planar structure.
Around the same time, Hermann Sachse postulated that rings were not flat, and potentially existed in other folded or twisted conformations. Ernst Mohr later combined the two theories to explain the stability of six-membered rings and their frequency in nature, as well as the energy levels of other ring structures.
In alkanes, optimum overlap of atomic orbitals is achieved at 109.5°, the mathematically ideal angle for tetrahedral geometry. The most common cyclic compounds have five or six carbons in their ring. Adolf von Baeyer received a Nobel Prize in 1905 for the discovery of the Baeyer strain theory, which was an explanation of the relative stabilities of cyclic molecules in 1885.
Angle strain occurs when bond angles deviate from the ideal bond angles to achieve maximum bond strength in a specific chemical conformation. Angle strain typically affects cyclic molecules, which lack the flexibility of acyclic molecules.
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Ring strain
In organic chemistry, ring strain is a type of instability that exists when bonds in a molecule form angles that deviate from their normal values as a result of being part of a ring. This type of strain is most commonly discussed for small rings such as cyclopropanes and cyclobutanes, whose internal angles are substantially smaller than the idealized value of approximately 109°. Because of their high strain, the heat of combustion for these small rings is elevated.
Ring strain results from a combination of angle strain, conformational strain or Pitzer strain (torsional eclipsing interactions), and transannular strain, also known as van der Waals strain or Prelog strain. The simplest examples of angle strain are small cycloalkanes such as cyclopropane and cyclobutane.
Ring strain energy can be attributed to the energy required for the distortion of bond and bond angles in order to close a ring.
The avoidance or reduction of ring strain can help direct or accelerate chemical reactions.
Ring strain theory was first developed by German chemist Adolf von Baeyer in 1890. Previously, the only types of strain believed to exist were torsional and steric; however, Baeyer's theory became based on the interactions between the two strains. Baeyer's theory was based on the assumption that the rings in cyclic compouns compounds were flat, and the simple geometry required for atoms in a planar structure.
Around the same time, Hermann Sachse postulated that rings were not flat, and potentially existed in other folded or twisted conformations. Ernst Mohr later combined the two theories to explain the stability of six-membered rings and their frequency in nature, as well as the energy levels of other ring structures.
In alkanes, optimum overlap of atomic orbitals is achieved at 109.5°, the mathematically ideal angle for tetrahedral geometry. The most common cyclic compounds have five or six carbons in their ring. Adolf von Baeyer received a Nobel Prize in 1905 for the discovery of the Baeyer strain theory, which was an explanation of the relative stabilities of cyclic molecules in 1885.
Angle strain occurs when bond angles deviate from the ideal bond angles to achieve maximum bond strength in a specific chemical conformation. Angle strain typically affects cyclic molecules, which lack the flexibility of acyclic molecules.