Basic strength: aliphatic vs aromatic amines
Amines and Diazonium Salts · Chemistry
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Why is aniline (pKb 9.4) a weaker base than methylamine (pKb 3.4)? Step 1: Basicity = availability of N's lone pair for H⁺. Step 2: Aniline: lone pair delocalizes into benzene ring (resonance) — less available. Step 3: Methylamine: +I methyl pushes electrons onto N — more available; conjugate acid well-solvated. Step 4: Resonance withdrawal vs inductive donation — aniline loses by 10⁶×! Delocalization decides.