Relationship Between Hybridization, Bond Length, and Reson

  • #1

Main Question or Discussion Point

Hello, I am currently taking Organic Chemistry and was wondering what is the relationship between bond length, hybridization, and resonance? In other words, do some hybridization have smaller bond length? How is that affected by resonance?
 

Answers and Replies

  • #2
S.S
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actually resonance governs the stability of a particular compound.So due to resonance there may be a partial double bond character induced eg. an amino group.Whenever there will be a partial double bond character, the bond length will decrease.
As for the amino group there is a partial double bond between the carbon and the NH2 group because the lone pair of nitrogen takes part in resonance.So the bond length of C-NH2 group becomes smaller.
 
  • #3
actually resonance governs the stability of a particular compound.So due to resonance there may be a partial double bond character induced eg. an amino group.Whenever there will be a partial double bond character, the bond length will decrease.
As for the amino group there is a partial double bond between the carbon and the NH2 group because the lone pair of nitrogen takes part in resonance.So the bond length of C-NH2 group becomes smaller.
smaller than a double bond?
 
  • #4
Quantum Defect
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smaller than a double bond?
"Partial double-bond character" means that the measured bond length is in between a C-N single and C=N double bond.

Generally, if you are able to draw a number of resonance structures for a molecule, the actual bonding is going to look like some kind of weighted average of the various bonds in the different resonance structures.

Benzene is the most obvious example here, with actual bond lengths equivalent, and having a bond length that would put the C-C bond somewhere between a typical single and a typical double bond.

Simple Molecular Orbital theory (a la Huckel) will help give better estimates of bonding character in individual bonds, and quantum chemistry calculations will provide even better results.
 

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