Why Does Methylamine Deprotonation Result in a Negative Charge on Nitrogen?

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When methylamine (CH3NH2) loses a proton, it forms CH3NH, which has a negative charge on the nitrogen atom, rather than CH2=NH2, which would have a positive charge on nitrogen. This phenomenon can be attributed to the stability of the resulting species and the concept of intramolecular proton transfer. The discussion highlights that the conjugate anion formed (CH3NH) is a stronger base than the amine hydrogen, making it less favorable for the intramolecular reaction to occur. The preference for nitrogen to bear the negative charge is also explained through electronegativity considerations, indicating that nitrogen is more capable of stabilizing a negative charge compared to carbon.
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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) ?
 
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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.
 
Think in terms of electronegativity. Which atom is more likely to bear a negative charge?
 

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