If the measurement of basic strength is conducted strictly in the gaseous phase, eliminating the com — GOC and Organic Chemistry Basics Chemistry Question
Question
If the measurement of basic strength is conducted strictly in the gaseous phase, eliminating the complex variables of solvent hydration and solvation energy, what is the correct decreasing sequence of basicity for simple alkylamines?
💡 Solution & Explanation
In the gas phase, the stabilization of the conjugate acid depends purely and exclusively on the inherent electronic effects of the molecule. Alkyl groups exert an electron-donating $+I$ inductive effect. The tertiary amine has three alkyl groups maximizing electron density on the nitrogen, making it the strongest base. The order follows strictly as $3^\circ > 2^\circ > 1^\circ > NH_3$.