193C Aminium salts and quaternary ammonium salts (胺盐和季胺盐) When primary, secondary, and tertiary amines act as bases and react with acids they form compounds called aminium salts (an amine salt) CH3 CH2NH HCl CH, CHNH2CI Ethylaminium chlorid H,O (CH3 CH2)2NH HCI (CH3 CH,)2NH,CI Die ethvlaminium chloride H2O (CH3CH2)3N HI (CH3CH2)3NH I Triethylaminium iodide
19.3C Aminium salts and quaternary ammonium salts (胺盐和季胺盐） When primary, secondary, and tertiary amines act as bases and react with acids, they form compounds called aminium salts. CH3CH2NH2 + HCl CH3CH2NH3Cl - + (CH3CH2 ) 2NH + HCl (CH3CH2 ) 2NH2Cl - H + 2O H2O (CH3CH2 ) 3N + HI (CH3CH2 )3NH l - H + 2O Triethylaminium iodide Diethylaminium chloride Ethylaminium chloride (an amine salt)
When the central nitrogen atom of a compound is positively charged but is not attached to a hydrogen atom the compound is called a quaterary ammonium salt. CH2CH3 CH3CH2—N—cH2CH3Br (CH3CH2)4N Br CH2CH3 Tetraethylammonium bromide (a quaternary ammonium salt)
When the central nitrogen atom of a compound is positively charged but is not attached to a hydrogen atom the compound is called a quaterary ammonium salt. CH3 CH2 + N CH2 CH3 CH2 CH3 CH2 CH3 Br - Tetraethylammonium bromide (a quaternary ammonium salt) (CH3 CH2 ) 4 N + Br -
Quaterary ammonium hydroxides (季胺碱) Quaternary ammonium hydroxides, however, are strong bases. As solids, or in solution, they consist entirely of quaternary ammoniu cations(RN and hydroxide ions(OH,); they are therefore strong bases---as strong as sodium or potassium hydroxide HOcH CH2CH2—N—cH2CH3OH (CH3CH24N OH CH2CH Tetraethylammonium hydroxide (a quaternary ammonium hydroxide (CH3 CH2)4NOH HCI (CH3CH2)4N'CI H2O
Quaterary ammonium hydroxides (季胺碱） Quaternary ammonium hydroxides, however, are strong bases. As solids, or in solution, they consist entirely of quaternary ammonium cations (R4N+ ) and hydroxide ions (OH- ); they are, therefore, strong bases---as strong as sodium or potassium hydroxide. CH3CH2 + N CH2CH3 CH2CH3 CH2CH3 OH - Tetraethylammonium hydroxide (a quaternary ammonium hydroxide) (CH3CH2 ) 4N +OH - (CH3CH2 )4N +OH - + HCl (CH3CH2 ) 4N +Cl - + H2O
19.3D Amines as resolving agents (胺作为拆分试剂) COOH NH2 H5l C6H5 CH3 R R- Amine Racemic(r,s)-acid cOo- COo NH3 H C6H5 C6H5 R R-Amine (R, R)-salt (S, R)-salt HCL H,O HCL,H,O COOH COOH OH C6H5 C6H5
19.3D Amines as resolving agents (胺作为拆分试剂） H OH COOH C6H5 HO H COOH C6H5 R- S- + C H 6H5 NH2 CH3 R- Amine H OH COO - C6H5 C H 6H5 NH3 CH3 R- R- Amine + (R, R)-salt HO H COOC6H5 S- C H 6H5 NH3 CH3 R- Amine + (S, R)-salt HCl, H2O HCl, H2O H OH COOH C6H5 R- HO H COOH C6H5 S- Racemic (R,S)-acid