Why is imidazole boiling point so high?

4.1. 1 Melting and boiling points. As a general rule the boiling points of imidazoles are relatively high, probably because of the high degree of intermolecular association. When there is a substituent other than hydrogen on an annular nitrogen, there is no longer any chance of such association.

Why boiling point of pyrrole is higher than furan and thiophene?

Pyrrole, furan and thiophene are colorless liquids of boiling points 126o, 32o, and 84o respectively. Pyrrole has a relatively high boiling point as compared to furan and thiophene, this is due to the presence of intermolecular hydrogen bonding in pyrrole.

Why does butanol have a high melting point?

The greatly increased boiling point is due to the fact that butanol contains a hydroxyl group, which is capable of hydrogen bonding.

Which is more basic imidazole or pyrazole?

Pyrazole is a weaker base than Imidazole. This is due to the sp2 orbital of nitrogen is the site of protonation in both pyrazole and imidazole. The nitrogen atom bonded to hydrogen is not basic because its lone pair of electrons is part of the aromatic ring system.

Why is imidazole more basic than pyridine?

Imidazole is more basic than pyridine. This is due to the greater resonance stabilization of the positive charge of its conjugate acid. Greater the pka value, the more basic the species become.

What is the boiling point of pyrrole?

264.2°F (129°C)
Pyrrole/Boiling point

Why furan has lower boiling point than pyrrole?

Which is more basic imidazole or pyrrole?

Imidazole is over a million times more basic than pyrrole because the sp2 nitrogen that is part of one double bond is structurally similar to pyridine, and has a comparable basicity.

Why does butanol have a higher boiling point than Butanal?

In butanol, due to the presence of hydroxyl group, there is formation of intermolecular hydrogen bonding. This results in molecular association. You need a large amount of energy to break these associations. Hence, the boiling point of butanol is higher than the boiling point of butanal.

Why does butanol have a higher boiling point than methanol?

Hydrogen bonds are much stronger than these; therefore, more energy is required to separate alcohol molecules than to separate alkane molecules. This is the main reason for higher boiling points in alcohols.

Why is imidazole more basic than pyrrole?

Indole (pKa = -2) and imidazole (pKa = 7.0), see above, also have similar heterocyclic aromatic rings. Imidazole is over a million times more basic than pyrrole because the sp2 nitrogen that is part of one double bond is structurally similar to pyridine, and has a comparable basicity.

Why imidazole is more basic than imidazole?

Aromaticity and resonance In this case imidizole, has aromatic 5-membered rings with six π electrons (Hückel rule). The situation is slightly different in imidazoline, as it has one lacking π bond and the system is not aromatic and thus no greater room for stabilisation due to delocalisation and hence more basic.

Is imidazole a stronger conjugate base than pyrrole?

Looking at imidazole it is stronger than pyrrole because the conjugate base is not only resonance stabalise but there are two electronegative atoms i-e Nitrogen to stabalize its negative charge. The answer is Yes! i can say this by comparing the stability of conjugate bases formed.

Why is imidazole pKa 7 more basic than pyridine?

The reason why the imidazole (pKa 7) is more basic than pyridine (pKa 5) is because protonated imidazole has two resonance forms such that both nitrogens contribute equally in carrying the positive charge. How did this girl break the private jet industry with just $250?

Why protonation of imidazole?

Why? Imidazole and its derivatives form an interesting and important class of heterocyclic aromatic amines. The basic strength of imidazole is approximately 100 times more basic than pyridine. Because protonation of imidazole yields an ion that is stabilized by the electron delocalization represented in the resonance structures given as below:

Why is the conjugate acid of imidazole ion equivalent to nitrogens?

Because protonation of imidazole yields an ion that is stabilized by the electron delocalization represented in the resonance structures given as below: As seen in above figure the electrostatic potential map of the conjugate acid of imidazole (imidazolium ion) is consistent with the resonance description that shows both nitrogens as equivalent.