Can Hydrogen undergo PI bonding?

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Discussion Overview

The discussion centers around whether hydrogen can form pi bonds, exploring theoretical and practical implications in chemistry. Participants examine the nature of hydrogen bonding, atomic orbitals, and specific molecular structures that may challenge conventional bonding theories.

Discussion Character

  • Debate/contested
  • Technical explanation
  • Conceptual clarification

Main Points Raised

  • Some participants argue that hydrogen cannot form pi bonds due to its single 1s orbital and the requirement for specific orbital symmetry for pi bonding.
  • Others suggest that while hydrogen typically forms only single bonds, there are exceptions in complex structures like carboranes where hydrogen appears to participate in multiple bonding scenarios.
  • One participant mentions that pi bonds can theoretically form with hydrogen if the necessary p-orbitals are available, although this is considered energetically unfavorable.
  • Another point raised is that pi bonds can exist without sigma bonds, citing the example of the C2 molecule, which consists solely of pi bonds.
  • There is a mention of "banana bonding" in a four-membered ring system, indicating potential interactions of p-orbitals that challenge traditional bonding models.

Areas of Agreement / Disagreement

Participants do not reach a consensus on whether hydrogen can form pi bonds. Multiple competing views are presented, with some asserting it is impossible while others suggest it is theoretically possible under certain conditions.

Contextual Notes

The discussion highlights limitations related to the symmetry of atomic orbitals and the energetic considerations of bonding, which remain unresolved. Specific examples and theoretical frameworks are referenced but not universally accepted.

Who May Find This Useful

This discussion may be of interest to students and professionals in chemistry, particularly those exploring molecular bonding theories and exceptions to traditional bonding rules.

VinnyCee
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I was wondering about Hydrogen and wether or not it can form Pi bonds.
 
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I don't think Hydrogen can form Pi bonds.

Since a double bond is made up out of one Sigma and one Pi bond, a Hydrogen atom would need to form a double bond for this to happen.
I don't see any reason why a Hydrogen atom would need to make a double bond since it is nice and stable with just a single bond. A Hydrogen atom only needs 1 additional electron to obtain a Noble gas configuration, so there would be no need for a double bond.
 
No, 1s atomic orbitals and pi atomic orbitals don't have the same symmetry, thus they don't interact to form molecular orbitals.
 
The only time I have ever seen hydrogens with forming more than 1 bond, if you can call it that, is in things like carborane cages. I'm not sure of the theory behind it, but carboranes are stable structures with hydrogens that have more than 1 bond.
 
If you take inorganic chemistry, you'll learn that, basically, any orbital (atomic or molecular) that has the same symmetry as the 1s atomic orbital of the hydrogen can interact (in relevance to group symmetry applications, such as LCAO and the theories). Two pz atomic orbitals, can approach the s orbital from opposite sides and interact with the proper symmetry, more or less covalent. Another example pertaining this subject that gravenewworld has mentioned is the cobaloximes, such as Co[R](dmgH)2(B), where the two dmgH molecules are coordinately bonded to the cobalt in a square planar fashion and are linked together by hydrogen bonds.

http://www.chm.bris.ac.uk/motm/vitaminb12/cobaloximes/CodmgH2RB.gif
 
mrjeffy321 said:
Since a double bond is made up out of one Sigma and one Pi bond...

its not always necessary that there be a sigma bond for the formation of a pi bond. the C2 molecule(yes, such a molecule exists), consists of only two pi bonds, making a double bond. however, in most cases a double bond is made up of one sigma and one pi bond, but not in this case.
 
If I am not mistaken, the formation of a pi bond requires side on side overlap of the px and py atomic orbitals. Seeing as hydrogen only has a single 1s orbital, it is energetically unfavourable and/or impossible to form a pi bond to hydrogen.
 
It is theoretically possible to have a pi-bond to hydrogen, the necessary p-orbitals are there, but they are relatively high in energy. So, I would agree with jer83 that it is energetically unfavorable, although not impossible.

And there are examples of pi bonds without sigma bonds. I saw someone talk about a 4-membered ring system where there was evidence of an interaction of two p-orbitals on atoms at opposite corners of the ring. They referred to it as "banana bonding."
 

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