How do zwitterions behave in different solutions and solid states?

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Zwitterions, such as alanine, feature both a positively charged ammonium group (NH3+) and a negatively charged carboxylate group (COO-), resulting in a net neutral charge. In a neutral environment, alanine exists in this zwitterionic form. When introduced to an alkali solution, the hydroxide ions (OH-) interact with the NH3+ group, leading to a reaction that may seem counterintuitive since both are classified as bases. However, the NH3+ group can be considered acidic in this context. The discussion also touches on whether alanine retains its zwitterionic form in solid state, suggesting that while it may not strictly exist as a zwitterion in solid form, hydrogen bonding between the carboxylic acid (COOH) and amine (NH2) groups likely influences its crystalline structure. The complexities of these interactions highlight the nuanced behavior of amino acids in different environments.
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Hi, I'm wondering how zwitterions works? For example, alanine.

NH3+-CH(CH3)-COO-

This is when it is in a neutral form right? But my teacher taught me that, when you add it into a alkali or acid solution. Let's take alkali for instance, the OH- reacts with the NH3+. But by my knowledge, OH- would mean a basic solution and NH3+ is a base. How could a base react with a base?
 
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Thanks for the reply. I'm clear now. So when alanine is in solid form, will it have the zwitterion form? the NH3+ end and COO- end? Or does this only occur in water/acid/alkali ?
 


I doubt it will be strictly zwitterion. However, without knowing exact crystallic structure it can be difficult to predict what is going on in the solid. Seems logical that hydrogen bonding between COOH and NH2 plays some role in the crystal structure.
 

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