Pka Bases

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pKa Values of Common Bases

Values in H2O as much as possible, so common comparisons (i.e., H2O pKa = 15.7) can still be used

Note; The pKa values associated with bases is normally meant to refer to the true pKa's of their conjugate
acids; i.e., pKa associated with HO- is 15.7, which is the pKa of H2O. This is often sloppily used by
organic chemists, and can lead to confusion, especially with amines.

CH3 H3C CH3


O H3C OH
H H H3C OH
H3C OH H3C OH
CH3 H3C CH3
base is H O- H3C O-
H3C O-
H3C O- H3C O-
pKa 15.7 pKa 15-16 pKa 16 pKa 16.5 pKa 17
hydroxide methoxide ethoxide isopropoxide tert-butoxide

O O
R R
- N+
O OH R H H3C OH
O the very weak bases
O
base is - - :NR3
O O
H3C O-

pKa 10 pKa 9-10 pKa 4.76


carbonate amine acetate
(carboxylate)

H2 (H-H)
NH3 N
H N
H
base is -
NH2
Na-H
N-Li+ or
N- K-H
Li+
pKa 35 pKa 35.7 pKa 37.1 pKa 35
amide lithium diisopropyl amide lithium tetramethyl- hydride bases
LDA piperidide (LiTMP)

H H H H H H H CH3
CH3
H H H3C H H3C H3C CH3

Li Li CH3
H3C Li CH3 H3C CH3
base is CH3-Li H3C

pKa 48 pKa 50 pKa 51 pKa (53)?


methyllithium n-butyllithium sec-butyllithium tert-butyllithium
MeLi n-BuLi s-BuLi t-BuLi

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