Amine protonation and nitrogen lone-pair availability
An amine's basicity can be described by the acidity of its conjugate ammonium species under specified conditions.
Key knowledge
An amine's basicity can be described by the acidity of its conjugate ammonium species under specified conditions. Resonance and substituent environment affect nitrogen lone-pair availability; amide nitrogen is generally much less basic than ordinary amine nitrogen because of carbonyl delocalization. Protonation can change solubility and extraction partitioning.
Conditions and scope
- Solvent, temperature and ionic environment must accompany pKa comparisons; basicity and nucleophilic rate are distinct.
- Reduced amide-nitrogen basicity does not mean an amide cannot protonate at any atom under any acidic condition.
Sources · 1
References
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Evidence and review
Read conjugate-acid relation, amide resonance and extraction discussion; excluded universal pKa+pKb=14 and amides-unprotonatable wording.
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Entry details
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- uni-chem-amine-protonation
- Revision
- core.1
- Structured reference record
- University core expansion