Acid -Base Chemistry - ChemConnections：酸-碱化学chemconnections.pptVIP

Amines Chemical / Biological / Neurological Activity Measures of Basicity The basicity of amines may be measured by: 1) Kb 2) pKb 3) Ka of conjugate acid 4) pKa of conjugate acid Basicity Constant (Kb) and pKb Kb is the equilibrium constant for the reaction: Ka and pKa of Conjugate Acid Ka is the equilibrium constant for the dissociation of the conjugate acid of the amine: Relationships between acidity and basicity constants A natural base from Erythroxylon spp. It is very valuable. The leaves are chewed by indigenous tribes in the Andes to boost their energy. It has been used as a psycho-therapeutic, an opthalmic anesthetic and was purportedly used in a popular beverage that is at the heart of a $20 billion corporation. However, both its base and conjugate acid are currently controlled substances under U.S. Federal Regulations: Title 21 secs. 329.1 1308.12 (1987). Can you name the beverage and the base? The beverage reportedly produced using the extract of leaves of Erythroxylon coca: Acid -Base Chemistry(Physical Properties) m.p. 98 oC b.p. (very volatile 90 oC) Solubility: Water: 1.67 x 10-3 g/mL CHCl3: 1.43 g/mL Ether: 0.29 g/mL “Regular” Cocaine Conjugate Acid of Cocaine(Physical Properties) m.p. 195 oC Solubility: Water: 2.5 g/mL CHCl3: 0.08 g/mL Ether: insoluble Acid -Base Reactions Acid Base Reactions Basicity of Amines in Aqueous Solution Amine Conj. Acid pKa NH3 NH4+ 9.3 CH3CH2NH2 CH3CH2NH3+ 10.8 Effect of Structure on Basicity 1. Alkylamines are slightly stronger bases than  ammonia. 2. Alkylamines differ very little in basicity. Basicity of Amines in Aqueous Solution Amine Conj. Acid pKa NH3 NH4+ 9.3 CH3CH2NH2 CH3CH2NH3+ 10.8 (CH3CH2)2NH (CH3CH2)2NH2+ 11.1 (CH3CH2)3N (CH3CH2)3NH+ 10.8 Effect of Structure on Basicity 1. Alkylamines are slightly stronger bases than  ammonia. 2. Alkylamines differ very little in basicity. 3. Arylamines are much weaker bases than ammonia. Basicity of Amines in Aqueous Solution Amine Con