Naming Amines Complex amines with more than one functional group are named by considering the-NH2 as an amino substituent on the parent molecule CO2H NH2 NH2 CH3CH2CHCO2H H2NCH2CH2CCH3 4321 4321 NH2 2-Aminobutanoic acid 2,4-Diaminobenzoic acid 4-Aminobutan-2-one
Complex amines with more than one functional group are named by considering the –NH2 as an amino substituent on the parent molecule Naming Amines
Naming Amines Symmetrical secondary and tertiary amines are named by adding the prefix di-or tri-to the alkyl group CH3CH2-N-CH2CH3 CH2CH3 Diphenylamine Triethylamine
Symmetrical secondary and tertiary amines are named by adding the prefix di- or tri- to the alkyl group Naming Amines
Naming Amines Unsymmetrically substituted secondary and tertiary amines are named as N-substituted primary amines Largest alkyl group is chosen as the parent name Other alkyl groups are considered N-substituents on the parent N because they are attached to nitrogen CH2CH3 H3C N-CH2CH2CH3 HgC N,N-Dimethylpropylamine N-Ethyl-N-methylcyclohexylamine
Unsymmetrically substituted secondary and tertiary amines are named as N-substituted primary amines ▪ Largest alkyl group is chosen as the parent name ▪ Other alkyl groups are considered N-substituents on the parent ▪ N because they are attached to nitrogen Naming Amines
Naming Amines Heterocyclic amines Compounds in which the nitrogen atom occurs as part of a ring Each different heterocyclic ring system has its own parent name -The heterocyclic nitrogen atom is always numbered as position 1 Pyridine Pyrrole Quinoline Imidazole Indole Pyrimidine Pyrrolidine Piperidine
Heterocyclic amines ▪ Compounds in which the nitrogen atom occurs as part of a ring ▪ Each different heterocyclic ring system has its own parent name ▪ The heterocyclic nitrogen atom is always numbered as position 1 Naming Amines
18-2 Properties of Amines Nitrogen atom in alkylamines is sp3-hybridized Three substituents occupy the three corners of a tetrahedron and the lone pair of electrons occupies the fourth corner Bond angles are close to 109 sp3-hybridized HgC CH3 H3C Trimethylamine
Nitrogen atom in alkylamines is sp3 -hybridized ▪ Three substituents occupy the three corners of a tetrahedron and the lone pair of electrons occupies the fourth corner ▪ Bond angles are close to 109° 18-2 Properties of Amines