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E, Z

The approved stereodescriptors of stereoisomeric alkenes R1R2C=CR3R4 ( R1R2 , R3R4 ); neither R1 nor R2 need be different from R3 or R4 ), cumulenes R1R2C(=C=C)n=CR3R4 and related systems e.g. R1R2C=NOH , HON=C{[CH2]n}2C=NOH . The group of highest CIP priority 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 bond order between one and two; and to double bonds involving elements other than carbon. They are not used to describe ring substitution relationships.
PAC, 1996, 68, 2193 (Basic terminology of stereochemistry (IUPAC Recommendations 1996)) on page 2206
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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.
Last update: 2014-02-24; version: 2.3.3.
DOI of this term: doi:10.1351/goldbook.E01882.
Original PDF version: http://www.iupac.org/goldbook/E01882.pdf. The PDF version is out of date and is provided for reference purposes only.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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