E, Z

https://doi.org/10.1351/goldbook.E01882
The approved @S05976@ of stereoisomeric @A00224@R1R2C=CR3R4 ( R1R2 , R3R4 ); neither R1 nor R2 need be different from R3 or R4 ), @C01440@R1R2C(=C=C)n=CR3R4 and related systems e.g. R1R2C=NOH , HON=C{[CH2]n}2C=NOH . The group of highest @C01082@ attached to one of the terminal doubly bonded atoms of the alkene, oxime, etc. or cumulene (i.e. R1 or R2 ) is compared with the group of highest precedence attached to the other (i.e. R3 or R4 ). The stereoisomer is designated as Z (zusammen = together) if the groups lie on the same side of a reference plane passing through the double bond and perpendicular to the plane containing the bonds linking the groups to the double-bonded atoms; the other stereoisomer is designated as E (entgegen = opposite). The descriptors may be applied to structures with a fractional @B00707@ between one and two; and to double bonds involving elements other than carbon. They are not used to describe ring substitution relationships.
See also:
cis-trans isomers
Source:
PAC, 1996, 68, 2193. (Basic terminology of stereochemistry (IUPAC Recommendations 1996)) on page 2206 [Terms] [Paper]