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Earlier this year, there was a lot of attention when all-cis 1,2,3,4,5,6-hexafluorocyclohexane was synthesized*:

perfluorocyclohexane

Notably, C&E News quoted the lead author:

This compound is remarkable for being the most polar nonionic compound now known to exist

Now, the original paper reports a molecular dipole moment of 6.2 D$\pu{6.2 D}$, which is extremely high for an alkane. It also claims the:

unusual property of a facially polarized ring in organic chemistry

Certainly having one side of the cyclohexane ring completely substituted with fluorines is unusual, so I agree with the facial-polarity property being interesting.

But there are many small molecules (e.g., under 20-30 atoms) with large dipole moments, e.g., p-nitroaniline:

enter image description here

A quick PM7PM7 calculation gives the predicted dipole moment of 7.93 $\pm$ 1 D$\pu{7.93\pm1 D}$. So I dispute the claim from C&E News - nitroaniline is clearly more polar and non-ionic.

So my question is this..: What's the largest dipole moment for a known non-ionic organic molecule under 30 atoms?

*: O'Hagan, et. al, "All-cis 1,2,3,4,5,6-hexafluorocyclohexane is a facially polarized cyclohexane" Nature Chemistry 7, 483–488 (2015)

Earlier this year, there was a lot of attention when all-cis 1,2,3,4,5,6-hexafluorocyclohexane was synthesized*:

perfluorocyclohexane

Notably, C&E News quoted the lead author:

This compound is remarkable for being the most polar nonionic compound now known to exist

Now, the original paper reports a molecular dipole moment of 6.2 D, which is extremely high for an alkane. It also claims the:

unusual property of a facially polarized ring in organic chemistry

Certainly having one side of the cyclohexane ring completely substituted with fluorines is unusual, so I agree with the facial-polarity property being interesting.

But there are many small molecules (e.g., under 20-30 atoms) with large dipole moments, e.g., p-nitroaniline:

enter image description here

A quick PM7 calculation gives the predicted dipole moment of 7.93 $\pm$ 1 D. So I dispute the claim from C&E News - nitroaniline is clearly more polar and non-ionic.

So my question is this.. What's the largest dipole moment for a known non-ionic organic molecule under 30 atoms?

*: O'Hagan, et. al, "All-cis 1,2,3,4,5,6-hexafluorocyclohexane is a facially polarized cyclohexane" Nature Chemistry 7, 483–488 (2015)

Earlier this year, there was a lot of attention when all-cis 1,2,3,4,5,6-hexafluorocyclohexane was synthesized*:

perfluorocyclohexane

Notably, C&E News quoted the lead author:

This compound is remarkable for being the most polar nonionic compound now known to exist

Now, the original paper reports a molecular dipole moment of $\pu{6.2 D}$, which is extremely high for an alkane. It also claims the:

unusual property of a facially polarized ring in organic chemistry

Certainly having one side of the cyclohexane ring completely substituted with fluorines is unusual, so I agree with the facial-polarity property being interesting.

But there are many small molecules (e.g., under 20-30 atoms) with large dipole moments, e.g., p-nitroaniline:

enter image description here

A quick PM7 calculation gives the predicted dipole moment of $\pu{7.93\pm1 D}$. So I dispute the claim from C&E News - nitroaniline is clearly more polar and non-ionic.

So my question is this: What's the largest dipole moment for a known non-ionic organic molecule under 30 atoms?

*: O'Hagan, et. al, "All-cis 1,2,3,4,5,6-hexafluorocyclohexane is a facially polarized cyclohexane" Nature Chemistry 7, 483–488 (2015)

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Geoff Hutchison
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Is PerfluorocyclohexaneHexafluorocyclohexane the "Most Polar" Small Molecule?

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bon
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Geoff Hutchison
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