Descriptors which show the relationship between two ligands attached to separate atoms that are connected by a double bond or are contained in a ring. The two ligands are said to be located cis
to each other if they lie on the same side of a plane. If they are on opposite sides, their relative position is described as trans
. The appropriate reference plane of a double bond is perpendicular to that of the relevant σ-bonds and passes through the double bond. For a ring (the ring being in a conformation, real or assumed, without re-entrant angles at the two substituted atoms) it is the mean plane of the ring(s). For alkenes the terms cis
may be ambiguous and have therefore largely been replaced by the E, Z
convention for the nomenclature of organic compounds. If there are more than two entities attached to the ring the use of cis
requires the definition of a reference substituent.
Blue Book Guide, p. 149 (https://doi.org/10.1351/pac199971071327)
PAC, 1996, 68, 2193. 'Basic terminology of stereochemistry (IUPAC Recommendations 1996)' on page 2203 (https://doi.org/10.1351/pac199668122193)