Organic BP question

[hasanein4u]

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Hey guys,

Could anybody rank the following structures according to their boiling point from lowest to highest with explanation:

1- o-phenylendiamine
2- m-phenylendiamine
3- p-phenylendiamine

and does it have the same trend if we altered the amino groups by 2 nitro groups or two chloro groups?

 

[Dgeorg6]

I would assume the farther apart they are from the -oh the higher the BP but idk lol

 

[Dotoday]

Para would have the highest BP because it will participate in Intermolecular H- bonding ( substituents are far apart). Ortho would have the lowest BP because of Intramolecular H- bonding ( substituents are closer together). Intermolecular hydrogen bond is usually more stable than intramolecular H- bond, due to the more surface area. Hope this helps.

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