422 Exam2 Heterocycles and Beta-lactams

oxirane

aziridine

thiirane

azetidine

thietane

1,3-dithietane

oxetane

Penam

Penem

Cephem

Carbapenam

Carbapenem

Carbacephem

Oxapenam

Clavam

Oxacephem

Monobactam

oxepine

oxepane

azepane

thiepane

azepine

thiepine

1H-1,4-diazepine

1,4-thiazepine

1,4-diazepane

1,3-diazepane

1,2-diazepane

1H-benzo[b][1,4]diazepine

benzo[b][1,4]thiazepine

benzodiazepine

pKa=3.4

furan/oxole

tetrahydrofuran/oxolane

thiole/thiophene

thiolane (tetrahydrothiophene)

pyrrole

pKa1=-3.8

pKa2=17.5

pyrrolidine

Imidazole

pKa1=6.9

pKa2=14.4

thiazole

pKa=2.5

oxazole

pKa=0.8

isoxazole

pKa=-3

isothiazole

1,2,3-triazole

1,2,4-triazole

tetrazole

indole

pKa1=-2.4

pKa2=16.2

benzothiophene

benzoimidazole

benzothiazole

benzoxazole

purine

adenine

guanine

xanthines

piperidine

morpholine

pyridine

pKa=5.2

pyridazine

pKa=2.3

pyrimidine

pKa=1.3

pyrazine

pKa=0.4

cinnoline

quinoline

isoquinoline

quinazoline

quinoxaline

Chromone

Coumarin

Benzofuran

benzotriazole

oxetene

thiete