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Gaurang Tandon
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Experimentally, acetonitrile has a larger dipole moment than acetaldehyde, but I've never understood why.

I always thought that the charge separation between carbon/oxygen is larger than that of carbon/nitrogen, and since the $\ce{C=O}$ bond should be longer than the $\ce{C#N}$ bond, the dipole moment $\mu = \delta d$ would be larger with both larger charge separation and larger distance.

I assume geometry might have something to do with it but I can't really explain such a large boiling point difference.


Data: Dipole moment values:

  • acetonitrile: $\approx \pu{3.4D}-\pu{3.5D}$ (source)
  • acetaldehyde: $\approx \pu{2.7D}$ (sources: 1, 2)

Experimentally, acetonitrile has a larger dipole moment than acetaldehyde, but I've never understood why.

I always thought that the charge separation between carbon/oxygen is larger than that of carbon/nitrogen, and since the $\ce{C=O}$ bond should be longer than the $\ce{C#N}$ bond, the dipole moment $\mu = \delta d$ would be larger with both larger charge separation and larger distance.

I assume geometry might have something to do with it but I can't really explain such a large boiling point difference.

Experimentally, acetonitrile has a larger dipole moment than acetaldehyde, but I've never understood why.

I always thought that the charge separation between carbon/oxygen is larger than that of carbon/nitrogen, and since the $\ce{C=O}$ bond should be longer than the $\ce{C#N}$ bond, the dipole moment $\mu = \delta d$ would be larger with both larger charge separation and larger distance.

I assume geometry might have something to do with it but I can't really explain such a large boiling point difference.


Data: Dipole moment values:

  • acetonitrile: $\approx \pu{3.4D}-\pu{3.5D}$ (source)
  • acetaldehyde: $\approx \pu{2.7D}$ (sources: 1, 2)
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Gaurang Tandon
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Acetonitrile vs Acetaldehyde Why does acetonitrile have a larger dipole moment and boiling pointspoint than acetaldehyde?

This has always been a puzzle for me. Experimentally, acetonitrile has a larger dipole moment than acetaldehyde, but I've never understood why.

I always thought that the charge separation between carbon/oxygen is larger than that of carbon/nitrogen, and since the $\ce{C=O}$ bond should be longer than the $\ce{C#N}$ bond, the dipole moment $\mu = \delta d$ would be larger with both larger charge separation and larger distance.

I assume geometry might have something to do with it but I can't really explain such a large boiling point difference.

Acetonitrile vs Acetaldehyde boiling points

This has always been a puzzle for me. Experimentally, acetonitrile has a larger dipole moment than acetaldehyde, but I've never understood why.

I always thought that the charge separation between carbon/oxygen is larger than that of carbon/nitrogen, and since the $\ce{C=O}$ bond should be longer than the $\ce{C#N}$ bond, the dipole moment $\mu = \delta d$ would be larger with both larger charge separation and larger distance.

I assume geometry might have something to do with it but I can't really explain such a large boiling point difference.

Why does acetonitrile have a larger dipole moment and boiling point than acetaldehyde?

Experimentally, acetonitrile has a larger dipole moment than acetaldehyde, but I've never understood why.

I always thought that the charge separation between carbon/oxygen is larger than that of carbon/nitrogen, and since the $\ce{C=O}$ bond should be longer than the $\ce{C#N}$ bond, the dipole moment $\mu = \delta d$ would be larger with both larger charge separation and larger distance.

I assume geometry might have something to do with it but I can't really explain such a large boiling point difference.

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ralk912
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This has always been a puzzle for me. Experimentally, acetonitrile has a larger dipole moment than acetaldehyde, but I've never understood why. 

I always thought that the charge separation between carbon/oxygen is larger than that of carbon/nitrogen, and since the $\ce{C=O}$ bond should be longer than the $\ce{C#N}$ bond, the dipole moment $\mu = \delta d$ would be larger with both larger charge separation and larger distance. 

I assume geometry might have something to do with it but I can't really explain such a large boiling point difference.

This has always been a puzzle for me. Experimentally, acetonitrile has a larger dipole moment than acetaldehyde, but I've never understood why. I always thought that the charge separation between carbon/oxygen is larger than that of carbon/nitrogen, and since the $\ce{C=O}$ bond should be longer than the $\ce{C#N}$ bond, the dipole moment $\mu = \delta d$ would be larger with both larger charge separation and larger distance. I assume geometry might have something to do with it but I can't really explain such a large boiling point difference.

This has always been a puzzle for me. Experimentally, acetonitrile has a larger dipole moment than acetaldehyde, but I've never understood why. 

I always thought that the charge separation between carbon/oxygen is larger than that of carbon/nitrogen, and since the $\ce{C=O}$ bond should be longer than the $\ce{C#N}$ bond, the dipole moment $\mu = \delta d$ would be larger with both larger charge separation and larger distance. 

I assume geometry might have something to do with it but I can't really explain such a large boiling point difference.

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ralk912
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