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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°.
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The substituted cyclooctyne is activated for a 1,3-dipolar cycloaddition by its ring strain and electron-withdrawing fluorine substituents, which allows the reaction to take place with kinetics comparable to the Cu-catalyzed Huisgen cycloaddition. Ring strain (~18 kcal/mol) arises from the deviation of the bond angles from the ideal 180° to ...
Due to ring strain, β-lactams are more readily hydrolyzed than linear amides or larger lactams. This strain is further increased by fusion to a second ring, as found in most β-lactam antibiotics. This trend is due to the amide character of the β-lactam being reduced by the aplanarity of the system.
The strain energy of cyclopropane and cyclobutane are 27.5 and 26.3 kcal mol −1, respectively. [1] Cyclopentane experiences much less strain, mainly due to torsional strain from eclipsed hydrogens: its preferred conformations interconvert by a process called pseudorotation. [4]: 14 Ring strain can be considerably higher in bicyclic systems.
In polymer chemistry, ring-opening metathesis polymerization (ROMP) is a type of chain-growth polymerization involving olefin metathesis. [1] The reaction is driven by relieving ring strain in cyclic olefins. [2] A variety of heterogeneous and homogeneous catalysts have been developed for different polymers and mechanisms. [3]
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Because the ring is highly strained, cyclopropene is difficult to prepare and highly reactive. This colorless gas has been the subject for many fundamental studies of bonding and reactivity. [2] It does not occur naturally, but derivatives are known in some fatty acids. Derivatives of cyclopropene are used commercially to control ripening of ...