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...

the ring shape allows for a larger area of contact. Containing only C–C and C–H bonds, unreactivity of cycloalkanes with little or no ring strain (see...

energy can be attributed to the ring strain of a five-membered ring which is absent in cyclohexane. Experimentally, strain energy is often determined using...

groups as being individual entities. Furthermore, this leaves error for ring strain, as we will see in its limitations. From this Benson and Buss concluded...

list isomers. Although subject to ring strain, 3-membered heterocyclic rings are well characterized. The 5-membered ring compounds containing two heteroatoms...

involving olefin metathesis. The driving force of the reaction is relief of ring strain in cyclic olefins (e.g. norbornene or cyclopentene). A variety of heterogeneous...

linked to each other to form a triangular ring. The small size of the ring creates substantial ring strain in the structure. Cyclopropane itself is mainly...

for example glucose. The favorability of the formation of a strain-free six-membered ring and the electrophilicity of an aldehyde combine to strongly...

within the cyclopentane ring is sp3 hybridized with the theoretical C-C-C bond angles near 108 degrees. Therefore ring strain is less prominent compared...

display aromaticity. It is not aromatic, however, because various types of ring strain destabilize an all-planar geometry.: 121–122  Although not aromatic itself...

electron-withdrawing, propargylic, gem-fluorines act together with the ring strain to greatly destabilize the alkyne. This destabilization increases the...

ether forms a three-atom ring: two atoms of carbon and one atom of oxygen. This triangular structure has substantial ring strain, making epoxides highly...

fewer carbons in the ring will not occur under normal conditions because of the large amount of ring strain needed. In larger rings (8 or more atoms), cis–trans...

but the nature of the ring creates substantial ring strain. As a result, cyclooctyne and other compounds containing this ring structure readily react...

phosphorus—phosphorus single bonds. The tetrahedral arrangement results in ring strain and instability. Although both are called "white phosphorus", in fact...

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,...

cyclohexene ring with a methylene bridge between carbons 1 and 4. The molecule carries a double bond which induces significant ring strain and significant...

cis-isomer is much more stable; the ring-strain energies being 16.7 and 7.4 kcal/mol, respectively. A planar arrangement of the ring carbons would be too strained...

lactone rings. Smaller rings, between 5 and 8 atoms, are more thermodynamically favored over medium to large rings due to lower ring strain. Ring strain arises...

for the synthesis of biopolymers. Ring-opening of cyclic monomers is often driven by the relief of bond-angle strain. Thus, as is the case for other types...

their ring strain. Monomers with large ring strain, such as oxirane, are more reactive than 1,3-dioxepane which has considerably less ring strain. Rings that...

chemistry, transannular strain (also called Prelog strain after chemist Vladimir Prelog) is the unfavorable interactions of ring substituents on non-adjacent...

was the first one developed for Cu-free click chemistry; it had only ring strain to drive the reaction forward, and the kinetics were barely improved...

change. Diazirines and epoxides photolyze with a tremendous release in ring strain to carbenes. The former extrude inert nitrogen gas, but epoxides typically...

compounds. They are bicyclic ring systems containing a β-lactam moiety fused with a five-member thiazolidine ring. Due to ring strain and limitations on amide...

aryl rings, resulting in very high strain and a decrease in distortion energies. It was proposed that biaryl substitution increases ring strain and provides...

this class is indicative of a rapid escalation of angle strain with an inverse correlation to ring size. Analysis by photoelectron spectroscopy has indicated...

lowest angle and torsional strain of all the cycloalkanes; as a result cyclohexane has been deemed a 0 in total ring strain. Cyclohexane has two crystalline...

similar advantages and drawbacks. Although relieving the cyclopropane ring strain is of great assistance in the initial C-P bond, exhaustive alkyl substitution...

epoxide ring opening of oxetane Since epoxide is a three-membered ring molecule, it has a high degree of ring strain. Although the carbons in the ring system...