Heterociclos

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Baran, Richter
3 2 3 2 4 5 4 5 2 1 3 4 5 6 5 7 4 3

Essentials of Heterocyclic Chemistry-I
3 2 3 2 6 7 2 45 2 6 7 2 6 7 3 4 5 4 2 5 3 4 5 5 6 7 8 4 2 5 3

Heterocyclic Chemistry
4 5 4 3 2 3 4 5

Deprotonation ofN–H, Deprotonation of C–H, Deprotonation of Conjugate Acid

N

N N1
4 5 6

3

6 7 8

N1 H

NH
67 1

N1 H

Pyrrolidine pKa: 11.3,44
3 2 4 5 2 3

N9 H

8

N
1

N

N1 H
4

HN

N1 H
6 72-Pyrazoline
5

N1 H
5 4

2

N
1

N

N
2

Pyrazolidine
6 7 8 1

Quinazoline
N3 N2
3 2NCinnoline
3 4 5

N1

6

Pyrrole pKa: 23.0, 39.5

Carbazole pKa: 19.9
4 5 2 3 4 5 7 6

Isoindole
81 2 5

3H-Indole
4 3

N1 H

Pyrazole pKa: 19.8, 35.9

N N

N N1

3

N

N
2

N N1
6Pyrimidine pKa: 1.3

N1 H

N1

3-Pyrroline 2H-Pyrrole
3 2 4 5 5 2 6 7 4 3 5 4 3

N1 H

N
5 4 3

N1 HIndole pKa: 21.0, 38.1
3 2

2

8

N1

N

4 5 6

Pteridine
H N
4 5 6 6 7

Phthalazine
52-Pyrroline
4

Indolizine
4 5 3 2 5

Indoline pKa: 4.9
4 5 2 6 7 2 3 3 4 5

1,2,4-Triazine pKa:
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