E,Z-isomeria

E,Z-isomeria tai -nimeämistapa on orgaanisessa kemiassa geometrisen isomerian muoto, jota käytetään kaksoissidoksia sisältävistä orgaanisista yhdisteistä (alkeeneista) silloin, kun yhdisteen rakenteen kuvaamiseen ei voida käyttää cis-trans–nimeämistapaa. E,Z-isomeriaa esiintyy alkeeneilla silloin, kun kaksoissidoksen hiiliin on liittynyt kolme tai neljä erilaista atomia tai atomiryhmää (jotka eivät ole vetyatomeja). Tällöin käytetään E,Z-nimeämistapaa, joka määräytyy Cahn–Ingold–Prelog-prioriteettisääntöjen avulla eli kaksoissidokseen kiinnittyvien atomien tai substituenttien prioriteettijärjestyksen perusteella. Atomien prioriteettijärjestys määräytyy atomipainojen (järjestysluvun eli atomiluvun) mukaan. Jos painavimmat atomit (substituentit) ovat samalla puolella kaksoissidosta, on kysymyksessä Z-konfiguraatio (saks. zusammen ’yhdessä’), eri puolilla taas E-konfiguraatio (saks. entgegen ’vastakkain’).

2-kloori-2-buteenin E- ja Z-isomeerit.

E ja Z eivät ole synonyymejä nimityksien cis ja trans kanssa. Jos renkaassa on kaksoissidos, sitä sanotaan tavallisesti cis-sidokseksi (yhdellä puolella), mutta jos sidoksessa on kiinni rengasta raskaampi substituentti, kyseessä onkin E-sidos (vastakkain).

Lähteet

  • McMurry, J. (2008). Organic Chemistry, 7. painos. Lontoo: Thomson Brooks/Cole, s. 180–184.
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