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

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In summary, the conversation is discussing the reason behind the formation of CH3NH (with a negative charge on nitrogen) rather than CH2=NH2 (with a positive charge on nitrogen) when methylamine loses a proton. The conclusion is that the intramolecular reaction does not occur significantly due to the stronger basicity of the conjugate anion compared to the amine hydrogen, which is determined by electronegativity.
  • #1
bomba923
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Why is it that when methylamine ([tex] CH_3 NH_2 [/tex]) loses a proton,

you get [tex] CH_3 NH [/tex] (with a negative charge on nitrogen) rather than [tex] CH_2 = NH_2 [/tex] (with a positive charge on nitrogen) ?
 
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  • #2
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
Think in terms of electronegativity. Which atom is more likely to bear a negative charge?
 

1. How does quick deprotonation work?

Quick deprotonation is a process in which a proton (H+) is removed from a molecule or ion at a rapid rate. This is typically achieved by using a strong base or a catalyst to facilitate the removal of the proton.

2. What is the purpose of quick deprotonation in scientific research?

Quick deprotonation is often used in scientific research to study the reactivity and stability of different molecules and ions. It can also be used to synthesize new compounds or to understand the mechanism of certain chemical reactions.

3. How is quick deprotonation different from regular deprotonation?

The main difference between quick deprotonation and regular deprotonation is the speed at which the proton is removed. Quick deprotonation is a much faster process, usually occurring in a matter of seconds or milliseconds, while regular deprotonation can take hours or even days.

4. What techniques are commonly used for quick deprotonation?

Some commonly used techniques for quick deprotonation include using strong bases such as sodium hydroxide or potassium hydroxide, using a catalyst such as palladium or platinum, or using high temperatures or pressures to facilitate the removal of the proton.

5. Are there any risks or limitations associated with quick deprotonation?

As with any chemical reaction, there are potential risks associated with quick deprotonation, such as the release of harmful gases or the production of toxic byproducts. Additionally, not all molecules or ions can undergo quick deprotonation, as it depends on their structure and stability. It is important to carefully consider and plan for these risks and limitations before conducting any experiments involving quick deprotonation.

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