# Quick deprotonation question

1. Jun 13, 2005

### bomba923

Why is it that when methylamine ($$CH_3 NH_2$$) loses a proton,

you get $$CH_3 NH$$ (with a negative charge on nitrogen) rather than $$CH_2 = NH_2$$ (with a positive charge on nitrogen) ?

2. Jun 13, 2005

### GCT

So you're basically saying that an intramolecular proton transfer will occur, either that or you're basically asking on why the carbon hydrogen in less acidic then the one on the amine. If it is in reference to the latter...read you text. The intramolecular reaction does not occur appreciably (to my knowledge) because the conjugate anion is a stronger base than even the amine hydrogen.

3. Jun 13, 2005

### movies

Think in terms of electronegativity. Which atom is more likely to bear a negative charge?