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The boiling points of four para-derivatives of phenol are:

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How can we compare the boiling points of p-nitrophenol and p-aminophenol?

Apart from the hydroxyl group, p-nitrophenol has two oxygen atoms to form inter-molecular H-bonding. Whereas, p-aminophenol has a nitrogen atom and two hydrogen atoms to form inter-molecular H-bonding. Also, the molecular mass of p-nitrophenol is more than that of p-aminophenol.

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    $\begingroup$ what kind of bonds break during the change of state? $\endgroup$ – Nicolas Feb 20 at 7:33
  • $\begingroup$ @Nicolas As far as boiling point is concerned, our interest is limited to various inter-molecular forces between molecules, which will reduce in phase conversion from liquid to gas. $\endgroup$ – Apurvium Feb 20 at 9:51
  • $\begingroup$ And what kind of intermolecular bonding are possible in p-aminophenol but which is not possible in p-nitrophenol? $\endgroup$ – Nicolas Feb 20 at 10:17
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    $\begingroup$ Whatever consideration, note that the difference is just 5 °C. $\endgroup$ – Alchimista Feb 20 at 10:25
  • $\begingroup$ @Nicolas I can't think of any. Out of these two, which one has higher dipole moment? $\endgroup$ – Apurvium Feb 20 at 10:54

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