2
$\begingroup$

I'm not sure what the exact difference between a ylide and a betaine is...

Are both zwitterions?

Something along the lines of: ALL ylides are betaines, but not all betains are ylides(according to wikipedia the cation/anion group can be adjacent or nonadjacent)?

$\endgroup$
7
$\begingroup$

The more definitive source for chemistry terminology is the IUPAC Gold Book.

Betaine

Originally, the compound betaine, $\ce{(CH3)3N+–CH2C(=O)O−}$ (N,N,N-trimethylammonioacetate), and similar zwitterionic compounds derived from other amino acids. By extension, neutral molecules having charge-separated forms with an onium atom which bears no hydrogen atoms and that is not adjacent to the anionic atom. Betaines cannot be represented without formal charges.

Ylides

Compounds in which an anionic site $\ce{Y−}$ (originally on carbon, but now including other atoms) is attached directly to a heteroatom $\ce{X+}$ (usually nitrogen, phosphorus or sulfur) carrying a formal positive charge. They are thus 1,2-dipolar species of the type $\ce{R_mX+–Y−R_n}$.

So, ylides are not betaines and betaines are not ylides. Primarily due to the atoms in a ylide that contain the charges must be adjacent, and in betaines they must not be adjacent.

An example of a ylid would be the phosphonium ylid used in Wittig chemistry:

Ylid

Since it has adjacent positive and negative charges, it is classified as a ylid.

The addition of this ylid to a carbonyl compound would form a betaine (note that the mechanism of the Wittig reaction is now thought to be a concerted [2+2] cycloaddition leading to the oxaphosphetane immediately, without the intermediacy of the betaine):

Betaine

Note that the ylid has an alternate resonance form (the one with a P=C double bond) which has no formal charges, whereas the betaine cannot be drawn without formal charges.

$\endgroup$
  • $\begingroup$ Quite nice answer. Welcome to Chemistry SE! $\endgroup$ – Mithoron Aug 19 '16 at 1:13
  • $\begingroup$ Great answer. It seems wiki has got it wrong. $\endgroup$ – Nova Aug 19 '16 at 1:58
  • $\begingroup$ @Nova Wiki is a great starting point, but not always technically correct. $\endgroup$ – orthocresol Aug 19 '16 at 2:38
  • $\begingroup$ You can format your posts using MathJaX: meta.chemistry.stackexchange.com/questions/86/… $\endgroup$ – orthocresol Aug 19 '16 at 2:38

Your Answer

By clicking “Post Your Answer”, you agree to our terms of service, privacy policy and cookie policy

Not the answer you're looking for? Browse other questions tagged or ask your own question.