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- Anomeric_effect abstract "In organic chemistry, the anomeric effect or Edward-Lemieux effect is a stereoelectronic effect that describes the tendency of heteroatomic substituents adjacent to a heteroatom within a cyclohexane ring to prefer the axial orientation instead of the less hindered equatorial orientation that would be expected from steric considerations. This effect was originally observed in pyranose rings by J. T. Edward in 1955 when studying carbohydrate chemistry.The term "anomeric effect" was introduced in 1958. The name comes from the term used to designate the C-1 carbon of a pyranose, the anomeric carbon. Isomers that differ only in the configuration at the anomeric carbon are called anomers. The anomers of glucopyranose are diastereomers, with the beta anomer having an OH group pointing up equatorially, and the alpha anomer having that OH group pointing down axially.The anomeric effect can also be generalized to any cyclohexyl or linear system with the general formula C-Y-C-X, where Y is a heteroatom with one or more lone pairs, and X is an electronegative atom or group. The magnitude of the anomeric effect is estimated at about 1–2 kcal/mol in the case of sugars, but is different for every molecule.In the above case, the methoxy group on the cyclohexane ring (top) prefers the equatorial position. However, in the tetrahydropyran ring (bottom), the methoxy group prefers the axial position. This is because in the cyclohexane ring, Y= carbon, which is not a heteroatom, so the anomeric effect is not observed and sterics dominates the observed substituent position. In the tetrahydropyran ring, Y= oxygen, which is a heteroatom, so the anomeric effect contributes and stabilizes the observed substituent position. In both cases, X= OMe.The anomeric effect is most often observed when Y= oxygen, but can also be seen with other lone pair baring heteroatoms in the ring, such as nitrogen, sulfur, and phosphorus.The exact method by which the anomeric effect causes stabilization is a point of controversy, and several hypotheses have been proposed to explain it.".
- Anomeric_effect thumbnail Glucoseab.png?width=300.
- Anomeric_effect wikiPageExternalLink anomeric-argument.
- Anomeric_effect wikiPageID "3901787".
- Anomeric_effect wikiPageRevisionID "603293328".
- Anomeric_effect hasPhotoCollection Anomeric_effect.
- Anomeric_effect subject Category:Acetals.
- Anomeric_effect subject Category:Carbohydrate_chemistry.
- Anomeric_effect subject Category:Carbohydrates.
- Anomeric_effect subject Category:Physical_organic_chemistry.
- Anomeric_effect type Abstraction100002137.
- Anomeric_effect type Acetal114710805.
- Anomeric_effect type Acetals.
- Anomeric_effect type Carbohydrate114792703.
- Anomeric_effect type Carbohydrates.
- Anomeric_effect type Chemical114806838.
- Anomeric_effect type Compound114818238.
- Anomeric_effect type Macromolecule114944888.
- Anomeric_effect type Material114580897.
- Anomeric_effect type Matter100020827.
- Anomeric_effect type Molecule114682133.
- Anomeric_effect type OrganicCompound114727670.
- Anomeric_effect type Part113809207.
- Anomeric_effect type PhysicalEntity100001930.
- Anomeric_effect type Relation100031921.
- Anomeric_effect type Substance100019613.
- Anomeric_effect type Thing100002452.
- Anomeric_effect type Unit109465459.
- Anomeric_effect comment "In organic chemistry, the anomeric effect or Edward-Lemieux effect is a stereoelectronic effect that describes the tendency of heteroatomic substituents adjacent to a heteroatom within a cyclohexane ring to prefer the axial orientation instead of the less hindered equatorial orientation that would be expected from steric considerations. This effect was originally observed in pyranose rings by J. T.".
- Anomeric_effect label "Anomerer Effekt".
- Anomeric_effect label "Anomeric effect".
- Anomeric_effect label "Efecto anomérico".
- Anomeric_effect label "Effetto anomerico".
- Anomeric_effect label "アノマー効果".
- Anomeric_effect label "端基异构效应".
- Anomeric_effect sameAs Anomerer_Effekt.
- Anomeric_effect sameAs Efecto_anomérico.
- Anomeric_effect sameAs Effetto_anomerico.
- Anomeric_effect sameAs アノマー効果.
- Anomeric_effect sameAs m.0b5_0s.
- Anomeric_effect sameAs Q567574.
- Anomeric_effect sameAs Q567574.
- Anomeric_effect sameAs Anomeric_effect.
- Anomeric_effect wasDerivedFrom Anomeric_effect?oldid=603293328.
- Anomeric_effect depiction Glucoseab.png.
- Anomeric_effect isPrimaryTopicOf Anomeric_effect.