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3 AcidBasepKaTable PDF
3 AcidBasepKaTable PDF
pKa
Strongest Acid protonated nitro group protonated nitrile (nitrilium) protonated ketone protonated thiol (sulfonium)
O H H
Weakest Base
+ O N O
11.3
sp N+
CH3 C N H H CH3
sp2 O+
+ CH3 C N
10.1
O C
+ CH3
CH3 H
sp3 S+
O C
CH3
7.2
CH3 S
CH3 S
6.8
H
pKa 6.7
protonated ester
O C
H OCH2CH3
+ CH3
O C
OCH2CH3
6.5
(HCl) = 6.2
H + CH3 O C
H CH 3
O C
OH
OH
6.1
CH3 S
CH3 H
CH3 S
CH3
5.4
Group protonated ether protonated alcohol protonated amide (amidinium) carboxylic acid (e deficient) phosphoric acid
CH3CH2
pKa 3.6
+ CH3 CH2
2.4
O C
H NH2
+ CH3
O C
NH2
CF 3
O C
+ CF3
O C
0.2
O
O H HO P O OH
O HO P O OH
2.1
Group anilinium
pKa 4.6
carboxylic acid
CH 3
O C H N
+ CH3
O C
4.7
O
pyridinium
H
5.3
CH3 CH3
iminium
CH3
N C H N
N C H N N
5.5
imidazolium
7.0
pKa 7.2
H CH3
8.5
CH3
C H
H H O C H CH3 + CH3 O C
CH3
O C
H H
C H
O C
CH3
9.0
ammonium
CH3
CH3 N H CH3 O
CH3
CH3 N CH3 O
9.8
phenol
10.0
Group thiol
pKa 10.5
O C
!-ketoCH3CH2 ester O
O C
+ CH3 CH2
H H
C H
CH3
11.0
CH3 CH3 H
N C
CH3 H C H H H +
CH3 CH3
N C
CH3 C H H
11.0
phosphate (dibasic)
O O P O O N C H N H H
O O P O O H N C
12.4
guanidinium
CH3
N H
+ CH 3
N H
N H
13.2
Group imidazole
pKa 14.4
amide
CH3
O C
N H O
+ CH3
15.0
N H O
alcohol
CH3CH2 O C
CH3CH2 O C
15.9
ketone
H C H H H
H CH3
C H
CH3
20
ester
C H H
O C
H OCH2CH3
C H
O C
OCH 2CH3
24.5
pKa 25
H H C C N H
H C C N H
25
amine
CH 3
H N H
CH3 N H
35
benzylic C-H
H H C H
H C H +
41
Group
H H
pKa
benzene
43
vinyl hydrogen
H H C C H H
H C C H H
44
alkane hydrogen
CH3
H C H H
CH3
H C H
50
Weakest Acid
Strongest Base