Why is nitrogen basic while oxygen and flourine are not?

In summary, HF is a strongly reactive acid that can break down lots of oxides and can etch glass. Compared to the other halides (e.g. HCl pKa ~ -7, HBr pKa ~ -9), this is quite a high value. So, HF will dissociate, but not to the same extent as related compounds.
  • #1
CrimpJiggler
149
1
Nitrogen is a lewis base because it has a lone pair of electrons with which to form bonds with electrophiles. Oxygen has 2 lone pairs of electrons and halogens have 3. Why doesn't oxygen use any of its spare pairs of electrons to react with electrophiles?
 
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  • #2
Oxygen and fluorine are more electronegative than nitrogen, so it is less favorable for these atoms to share their lone pairs with an electrophile. This is not to say that it is impossible, for example, alcohols get protonated at very low pH (around -1 to -2).
 
  • #3
I want to say that Flourine is waaaaaaaaaay too reactive / unstable. . . it never exists as an ion irl.
 
  • #4
Ygggdrasil: that explains it, thanks.

Highway: So the F- ion is uncommon is it? I've read that HF is a weak acid but I don't know what its dissociation constant. Are you saying that HF doesn't actually dissociate at all?
 
  • #5
CrimpJiggler said:
Ygggdrasil: that explains it, thanks.

Highway: So the F- ion is uncommon is it? I've read that HF is a weak acid but I don't know what its dissociation constant. Are you saying that HF doesn't actually dissociate at all?
HF is a very strongly reactive acid that can break down lots of oxides and can etch glass.
 
  • #6
HF has a pKa of 3.17. Compared to the other halides (e.g. HCl pKa ~ -7, HBr pKa ~ -9), this is quite a high value. So, HF will dissociate, but not to the same extent as related compounds.
 
  • #7
CrimpJiggler said:
Nitrogen is a lewis base because it has a lone pair of electrons with which to form bonds with electrophiles. Oxygen has 2 lone pairs of electrons and halogens have 3. Why doesn't oxygen use any of its spare pairs of electrons to react with electrophiles?

Who sais so? H+ is quite electrophilic and readily reacts with H2O to form hydronium ions H3O+ and also FH2- forms stable salts. Other electrophiles? I think there are adducts of BF3 and various ethers. And of course you can make all kinds of electrophilic substitutions on oxygen. So its more a question of stability of the adducts with respect to further reactions. Finally there are salts like trimethyloxonium tetrafluoroborate (Meerwein salt).

Btw. its fluorine, not flourine.
 
  • #8
CrimpJiggler said:
Ygggdrasil: that explains it, thanks.

Highway: So the F- ion is uncommon is it? I've read that HF is a weak acid but I don't know what its dissociation constant. Are you saying that HF doesn't actually dissociate at all?

I remember this coming up in class and our prof saying that F- exists for only a very short time in solution, due to it's high reactivity.

Email your prof the same question -- he'll give you a better answer than I can, as I'm not a chemist.
 

1. Why is nitrogen considered a basic element while oxygen and fluorine are not?

Nitrogen is considered a basic element because it has a lower electronegativity value compared to oxygen and fluorine. This means that nitrogen is less likely to attract electrons towards itself, making it a weaker acid and therefore a basic element.

2. How does the electronegativity value affect the basicity of an element?

The electronegativity value of an element is a measure of its ability to attract electrons towards itself. Elements with lower electronegativity values are less likely to attract electrons, making them weaker acids and therefore basic in nature.

3. What other factors besides electronegativity contribute to the basicity of an element?

The atomic size and the number of valence electrons also play a role in determining the basicity of an element. Elements with larger atomic sizes and more valence electrons are more likely to donate electrons, making them basic.

4. Is there a specific group of elements that are more likely to be basic?

Yes, elements in Group 1 and Group 2 of the periodic table, also known as the alkali and alkaline earth metals, are more likely to be basic due to their low electronegativity values and large atomic sizes.

5. Can nitrogen ever act as an acid?

Yes, nitrogen can act as an acid in certain situations, such as when it is bonded with more electronegative elements. Its electronegativity value is still lower than oxygen and fluorine, but it is high enough to make it a weak acid in these cases.

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