定义Definition
E/Z 命名法用 CIP 规则分别确定双键两端各自优先的基团:两个优先基团在同侧为 Z(zusammen,在一起),异侧为 E(entgegen,相反)。
E/Z notation uses the CIP rules to find the higher-priority group at each end of a double bond: same side is Z (zusammen, together), opposite sides E (entgegen, opposite).
与顺反的区别Versus cis/trans
顺/反比较的是相同或相似基团,E/Z 比较的是优先基团,二者不一定一致:(Z)-1-溴-2-氯丙烯中 Br 与 Cl 同侧,但若按甲基与氢比较可能被称为“反式”。三、四取代烯烃只能用 E/Z 清楚描述。
Cis/trans compares identical or similar groups, E/Z the priority groups, and the two can disagree; tri- and tetrasubstituted alkenes can only be described unambiguously with E/Z.
适用范围Scope
也用于 C=N(肟、亚胺、腙)和 N=N(偶氮化合物)双键,此时孤对电子优先级最低。
Also used for C=N (oximes, imines, hydrazones) and N=N (azo) bonds, with a lone pair ranked lowest.
由来Origin
1968 年由布莱克伍德等提出,并入 CIP 体系,后被 IUPAC 采纳。
Introduced in 1968 by Blackwood and co-workers within the CIP framework and adopted by IUPAC.
年表Timeline
- 1968
E/Z 体系提出
E/Z system introduced