Which end of glycine would be more basic?

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In summary, the question posed is how to determine which end of a molecule is more basic and likely to be protonated. An analogy is made using the molecules CH3-OH and CH3-NH2, followed by the molecules H-OH and H-NH2. The questioner is wondering if there is a way to determine this without memorizing pKa values. The answerer suggests that for amino acids, the carboxyl group is acidic and the amino group is basic, making it easy to determine which end will be protonated.
  • #1
Avi_R
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I had a question given, regarding the basicity of certain sites on a molecule. For example, glycine:
glycine_min.gif


How would you determine whether the OH end or the NH2 end would be more "basic", or the first to get protonated?
 
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  • #2
Avi_R said:
I had a question given, regarding the basicity of certain sites on a molecule. For example, glycine:
glycine_min.gif


How would you determine whether the OH end or the NH2 end would be more "basic", or the first to get protonated?
Make an analogy and think about

1. CH3-OH
2. CH3-NH2

Which is more protonable?
In case you didn't find the answer, try with

1. H-OH = H2O
2. H-NH2 = NH3

Which is more protonable?
 
  • #3
What I'd like to know is how do I determine which is more protonable, without memorizing pka's.
 
  • #4
For the amino acids, one end has a carboxyl group (ie COOH) and the other end has the amino group. So, in this case, it's easy to figure out which end is acidic (ie, loses H+) and which end is basic (ie, accepts H+).
 

Related to Which end of glycine would be more basic?

What is the basicity of a certain site?

The basicity of a certain site refers to its ability to accept protons and form a positively charged species. It is a measure of the strength of an acid-base reaction and can be influenced by factors such as the electronic and steric environment of the site.

How is the basicity of a certain site determined?

The basicity of a certain site can be determined experimentally by measuring the equilibrium constant of an acid-base reaction involving that site. It can also be predicted using theoretical calculations and various spectroscopic techniques.

What factors influence the basicity of a certain site?

The basicity of a certain site can be influenced by the electronegativity of surrounding atoms, the availability of lone pairs of electrons, and the steric hindrance of nearby groups. Additionally, the solvent and temperature can also affect the basicity of a site.

What is the relationship between basicity and acidity?

Basicity and acidity are two sides of the same coin. A basic site is one that can accept protons, while an acidic site is one that can donate protons. The basicity and acidity of a certain site are related through the equilibrium constant of an acid-base reaction involving that site.

How does the basicity of a certain site affect the reactivity of a molecule?

The basicity of a certain site can greatly influence the reactivity of a molecule. A more basic site will be more likely to react with an acidic species, while a less basic site may be less reactive. The basicity of a site can also affect the stability and selectivity of a reaction.

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