Ylide

An ylide (/ˈɪld/)[1] or ylid (/ˈɪlɪd/) is a neutral dipolar molecule containing a formally negatively charged atom (usually a carbanion) directly attached to a heteroatom with a formal positive charge (usually nitrogen, phosphorus or sulfur), and in which both atoms have full octets of electrons. The result can be viewed as a structure in which two adjacent atoms are connected by both a covalent and an ionic bond; normally written X+–Y. Ylides are thus 1,2-dipolar compounds, and a subclass of zwitterions.[2] They appear in organic chemistry as reagents or reactive intermediates.[3]

The class name "ylide" for the compound should not be confused with the suffix "-ylide".

  1. ^ "ylide" – via The Free Dictionary.
  2. ^ IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "ylides". doi:10.1351/goldbook.Y06728
  3. ^ McMurry, John (2008). Organic Chemistry, 7th Ed. Thomson Brooks/Cole. pp. 720–722. ISBN 978-0-495-11258-7.