Axial chirality

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Axial chirality is a special case of chirality in which a molecule does not possess a stereogenic center (the most common form of chirality in organic compounds) but an axis of chirality - an axis about which a set of substituents is held in a spatial arrangement which is not superposable on its mirror image. Axial chirality is most commonly observed in atropisomeric biaryl compounds where the rotation about the aryl-aryl bond is restricted, for example biphenyl, binaphthyls e.g., 1,1'-bi-2-naphthol, and certain dihydroanthracenone compounds [1] . Certain allene compounds also display axial chirality. The enantiomers of axially chiral compounds are usually given the stereochemical labels Ra and Sa, although the plus (P) or minus (M) notation is occasionally employed.[2] P/M is used particularly for molecules which resemble a helix, such as hexahelicene, in which case a right-handed helix is denoted P and a left-handed helix is denoted M.[3]

External links

  • Axial Chirality in 6,6'-Dinitrobiphenyl-2,2'-dicarboxylic acid 3D representation Link

References

  1. Absolute stereochemistry of fungal metabolites: Icterinoidins A1 and B1, and atrovirins B1 and B2 Melvyn Gill and Peter M. Morgan Arkivoc (RI-1154C)2004 Online article
  2. Compendium of Chemical Terminology, axial chirality
  3. VLU: Additional Chirality Elements - Chemgapedia[1]

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