A planar unit connected to an adjacent part of the structure by a bond which results in restricted torsion so that the plane cannot lie in a symmetry plane. For example with (E
)-cyclooctene the chiral
plane includes the double bond carbon atoms and all four atoms attached to the double bond; with a monosubstituted paracyclophane the chiral
plane includes the monosubstituted benzene ring with its three hydrogen atoms and the three other atoms linked to the ring (i.e. from the substituent and the two chains linking the two benzene rings).
PAC, 1996, 68, 2193
(Basic terminology of stereochemistry (IUPAC Recommendations 1996))
on page 2203
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