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, crown conformer
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
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: http://goldbook.iupac.org (2006-) created by M. Nic, J. Jirat, B. Kosata; updates compiled by A. Jenkins. ISBN 0-9678550-9-8. doi:10.1351/goldbook