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Concept
Ring strain
Summary
In organic chemistry, ring strain is a type of instability that exists when bonds in a molecule form angles that are abnormal. 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.
Ring strain energy is believed to be the cause of accelerated rates in altering ring reactions. Its interactions with traditional bond energies change the enthalpies of compounds effecting the kinetics and thermodynamics of ring strain reactions.
Ring strain theory was first developed by German chemist Adolf von Bayer in 1890. Previously, the only bonds believed to exist were torsional and steric; however, Bayer's theory became based on the interactions between the two strains.
Bayer's theory was based on the assumption that ringed compounds were flat. Later, around the same time, Hermann Sachse formed his postulation that compound rings were not flat and potentially existed in a "chair" formation. 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 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.
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