Why isn't the ion NH4+ capable of hydrogen bonding?

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Discussion Overview

The discussion centers around the ion NH4+ and its capability to form hydrogen bonds. Participants explore the Lewis structure of NH4+, the presence of lone pairs, and the implications for hydrogen bonding, with considerations of related species like NH3.

Discussion Character

  • Technical explanation
  • Debate/contested
  • Conceptual clarification

Main Points Raised

  • Some participants propose that NH4+ has a central nitrogen atom with one lone pair and four single bonds to hydrogen, questioning the hydrogen bonding capability.
  • Others argue that NH4+ does not have a lone pair on nitrogen, as it forms four bonds with hydrogen, leading to confusion about the electron distribution.
  • A participant suggests that if NH4 were to exist with an additional electron, it might have implications for hydrogen bonding, but acknowledges that NH4 does not exist in a stable form.
  • Some participants clarify that NH4+ has four sp³ hybridized orbitals filled with electrons, leaving no orbitals available for hydrogen bonding.
  • There is a suggestion that NH4+ cannot form hydrogen bonds with itself but could interact with NH3 through hydrogen bonding due to the presence of lone pairs on NH3.
  • One participant introduces the concept of radicals, discussing the hypothetical placement of an unpaired electron in a molecule like ammonia.

Areas of Agreement / Disagreement

Participants generally disagree on the presence of lone pairs in NH4+ and its implications for hydrogen bonding. The discussion remains unresolved regarding the existence of NH4 and the behavior of unpaired electrons in related species.

Contextual Notes

Limitations include the lack of consensus on the Lewis structure interpretations and the stability of hypothetical species like NH4. The discussion also reflects uncertainty about the behavior of electrons in molecular orbitals.

dramadeur
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If you draw lewis structure, central atom (N) will have 1 lone pair and 4 single bonds with Hydrogen.
Why can't hydrogen in this ion molecule be able to form hydrogen bonding with other molecules alike?
Is it because there's only 1 electron on the central atom?See for yourself: 5N + 4H -1 = 9 electrons to go around.
4 bonds = 8 electrons
9 - 8 electrons = 1 electron left.
So this 1 electron is placed on the central atom.
 
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dramadeur said:
If you draw lewis structure, central atom (N) will have 1 lone pair and 4 single bonds with Hydrogen.

That's definitely wrong. No lone pair in NH4+.
 
Borek said:
That's definitely wrong. No lone pair in NH4+.
I've just updated my post. How can't there be?
Nitrogen has 5 valence e + 4 Hydrogen valence e -1 from the charge sign = 9 electrons to go around.
So... there's only 1 electron on the central atom?
 
5+4-1 is 9?
 
Yeah I dun goofed, sorry.
Anyway, if this molecule was just NH4, and it had 9 molecules, would it be capable of hydrogen bonding? Since it would have a electron on its central atom...
 
dramadeur said:
Anyway, if this molecule was just NH4, and it had 9 molecules, would it be capable of hydrogen bonding? Since it would have a electron on its central atom...

There is no atom orbital left to form a hydrogen bond. In NH4+ there are four binding sp³ hybride orbitals populated with each 2 electrons. An additional electron would be located in an anti-binding sp³ orbital resulting in a half bond for one of the four hydrogen atoms. I do not know if such a molecule exists, but it would be less stable than NH4+.
 
Just imagine that the lone pair that is necesary to form hydrogen bonding which is present on NH3, it is not present on NH4+, becasue "it's forming the bond with the fourth hydrogen".
 
Altered State said:
Just imagine that the lone pair that is necesary to form hydrogen bonding which is present on NH3, it is not present on NH4+, becasue "it's forming the bond with the fourth hydrogen".

However, that only means that NH4+ cannot form a hydrogen bond with another NH4+. But it can form a hydrogen bond with the electron pair of NH3 resulting in [H3N-H...NH3]+.
 
DrStupid said:
There is no atom orbital left to form a hydrogen bond. In NH4+ there are four binding sp³ hybride orbitals populated with each 2 electrons. An additional electron would be located in an anti-binding sp³ orbital resulting in a half bond for one of the four hydrogen atoms. I do not know if such a molecule exists, but it would be less stable than NH4+.
Uhm... I said NH4 not NH4+
What will the lewis structure be? Will it have 1 electron on the central atom?
 
  • #10
dramadeur said:
Uhm... I said NH4 not NH4+
What will the lewis structure be? Will it have 1 electron on the central atom?

NH4 will not exist.
If an NH3 molecule binds to another atom/molecule, a positive charge will be held by the nitrogen.
 
  • #11
Altered State said:
NH4 will not exist.
But what would happen to a single left out electron in any atom where it's possible? Would it be placed on the central atom... or? Where would it go?
 
  • #12
dramadeur said:
But what would happen to a single left out electron in any atom where it's possible? Would it be placed on the central atom... or? Where would it go?

It is more complicated than that, electrons are not placed in "concrete spots" of the molecules, you can say that they are in a given molecular orbital.
But for sake of simplification, you can say that in that hypothetical situation, the electron could be on the central atom and you would have an ammonia/ammonium radical. A radical is a species that happens to have 1 single electron in one atom.
This is not a common thing in a molecule like ammonia, but there are many radical forms of organic molecules, for example: http://www.masterorganicchemistry.com/2013/07/30/free-radical-reactions/
 

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