Basicity of Weak Bases

Molecule pKa(1) pKa(2) pKa(3) DH, kcal/mol, Gas (4)
PhCH3 41.2 43 39 381
Ph2CH2 33.4 32.3 31 --
Ph3CH 31.4 -- 30.6 --
Fluorene 22.7 22.6 -- 351.8
Indene 19.9 20.1 -- --
Cyclopentadiene 16.6 18.1 -- --
Methane -- -- 48 418.8
Ethane -- -- 51 419.0
Ethylene -- -- -- 407.5
Cyclopropane -- -- -- 411.5
Cyclopentane -- -- 49 --
Benzene -- -- -- 400.8
Cyclohexene 45 -- -- 386.5
Phenylacetylene 23.2 -- -- 370.7
Ammonia -- -- -- 403.6
Acetone -- 20 -- -48.5
tBuOH -- -- -- -65.8

1. Based on H exchange with cesium cyclohexylamide in cyclohexylamine

2. Based on H exchange with dimsyl potassium in DMSO

3. From electrochemical reduction of radicals in DMF

4. ICR measurements of BH = B- H+


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