CO

2

CO

NH

3

N

N

M

ethylenediamine

H

2

N-CH

2

-CH

2

-NH

2

H

2

H

2

CHELATY

O

H

2

O

H

2

N

O

M

N

O

glycine

H

2

N-CH

2

-COOH

O

O

O

O

M

O

O

O

O

O

O

OH

OH

tartrate

HOOC-CH-CH-COOH

OH

OH

O

O

HO

OH

OH

OH

=

N
H

N

H
N

N

N

N

N

N

Fe

COOH

COOH

N

O

O

O

H

N

N

N

N

N

N

N

N

O

S

O

N
H

7

quinoline

isoquinoline

1

2

3

3

4

5

6

7

8

2

4

3

5

7

6

indole

4

6

8

5

4H-pyran

(THP)

tetrahydropyran

2H-pyran

4

5

8

7

6

purine

2

pyridazine

pyrazine

pyrimidine

piperidyne

pyridyne

isooxazole

1

isothiazole

2

1

1

3

oxazole

O

N

thiazole

pyrazole

imidazole

S

N

N

N

N

H

N

N

N

H

1

(epoxide)

oxiran

(THF)

tetrahydrotiophene

tiophene

tetrahydrofuran

furan

pyrrolidine

pyrrole

S

O

N

H

N

N

piperazine

N

N

N

H

1

9

N

1

3

N

H

1

N

1

1

4

2

2

S

1

3

2

3

O

1

2

1

3

1

2

1

2

Acid

pK

a

Conjugate base

hexane

45

C

6

H

11

–

NH

3

/liquid

34

NH

2

–

HC



CH

25

HC



C

–

CH

3

CH

2

OH

18

CH

3

CH

2

O

–

H

2

O

14

HO

–

HPO

4

2–

12.32

PO

4

3–

HCO

3

–

10.33

CO

3

2–

Phenol

10

phenolate

NH

4

+

9.25

NH

3

H

2

PO

4

–

7.2

HPO

4

2–

H

2

S

7.04

HS

–

H

2

CO

3

6.3

HCO

3

–

CH

3

COOH

4.7

CH

3

COO

–

Ascorbic acid

4.1

ascorbate

HF

3.2

F

–

H

3

PO

4

2.12

H

2

PO

4

–

HNO

3

-1.0

NO

3

–

H

3

O

+

0

H

2

O

HCl

-7

Cl

–

H

2

SO

4

-9

HSO

4

–

HI , HClO

4

-10

I

–

, HClO

4

–

SbF

5

.

FSO

3

H

-12

SbF

5

.

FSO

3

–

increasing acidity

increasing basicity