Basicity Order of Amines

Rarely Tested

Gas-phase basicity:

$$\mathrm{R_3N} \gt \mathrm{R_2NH} \gt \mathrm{RNH_2} \gt \mathrm{NH_3}$$

Reason: +I effect (tertiary > secondary > primary > ammonia)


Aqueous basicity:

$$\mathrm{R_2NH} \gt \mathrm{RNH_2} \gt \mathrm{R_3N} \gt \mathrm{NH_3}$$

Reason: solvation > steric hindrance favors 2° > 1° > 3° > ammonia

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