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axial (equatorial)

Also contains definitions of: pseudo-axial, pseudo-equatorial, quasi-axial, quasi-equatorial

In the chair form of cyclohexane ring bonds to ring atoms (and molecular entities attached to such bonds) are termed axial or equatorial according to whether the bonds make a relatively large or small angle, respectively, with the plane containing or passing closest to a majority of the ring atoms. Thus the axial bonds are approximately parallel to the C3 axis and the equatorial bonds approximately parallel to two of the ring bonds. These terms are also used for the chair form of other saturated six-membered rings. The corresponding bonds occurring at the allylic positions in mono-unsaturated six-membered rings are termed pseudo-axial (or quasi-axial) and pseudo-equatorial (or quasi-equatorial). The terms axial and equatorial have similarly been used in relation to the puckered conformation of cyclobutane, crownconformer of cyclooctane, etc. and the terms pseudo-axial and pseudo-equatorial in the context of the non-planar structures of cyclopentane and cycloheptane.
See apical (basal, equatorial) for an alternative use of axial and equatorial with bipyramidal structures.
PAC, 1996, 68, 2193 (Basic terminology of stereochemistry (IUPAC Recommendations 1996)) on page 2200
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Cite as:
IUPAC. Compendium of Chemical Terminology, 2nd ed. (the "Gold Book"). Compiled by A. D. McNaught and A. Wilkinson. Blackwell Scientific Publications, Oxford (1997). XML on-line corrected version: (2006-) created by M. Nic, J. Jirat, B. Kosata; updates compiled by A. Jenkins. ISBN 0-9678550-9-8. doi:10.1351/goldbook.
Last update: 2014-02-24; version: 2.3.3.
DOI of this term: doi:10.1351/goldbook.A00546.
Original PDF version: The PDF version is out of date and is provided for reference purposes only. For some entries, the PDF version may be unavailable.
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