Amines
All Classes of Organic Compounds ydrocarbons Functionalized ydrocarbons F,Cl,Br O,S, Alkanes Alkenes Alkynes Aromatics alides -O- -S- -- Alcohols Phenols Ethers Thiols Dissulfides Amines O C O C O C-O O C- Aldehydes Ketones Acids Esters Anhydrides Amides
Amines - Derivatives of Ammonia Classification by the number of attached groups ethylamine diethylamine triethylamine a primary amine a secondary amine a tertiary amine
Quartenary Ammonium Ions ammonium ion C 2 C 3 [ C 3 C 2 C 2 C 3 ] C 2 C 3 tetraethyl ammonium.. (part of a name) a quaternary ammonium salt
Cyclic Amines pyrrolidine pyrimidine imidazole purine
Amines - Classification Classification by the type of attached groups aromatic amines 2 2 aliphatic amines 3 C 2 C 2 3 C C 2 3 C
Amines - omenclature Amines containing simple groups are named with common nomenclature. Simple groups include: Unbranched alkyl groups: methyl, ethyl, propyl, butyl,., decyl Branched 3- and 4-carbon alkyl groups: isopropyl, isobutyl, s-butyl, t-butyl Unsubstituted cycloalkyl groups: cyclohexyl and cyclopentyl C3 C2 C3 ethylmethylamine C3 C C3 2º 1º isopropylamine C3 cyclohexylmethylamine C3 C3 2º 3º C2C3 ethyldimethylamine
Amines - omenclature 2 2 3 C C 3 aniline 4-methyl aniline p-methyl aniline -methyl aniline
Amines - omenclature 2 C 2 C 2 C 2 COO 4-aminobutanoic acid C 3 C C 2 C 2 O 3 C C 3 3-(dimethylamino)-1-butanol C 3 C 3 C C C 2 C 3 C 3 3,-dimethyl-2-pentanamine
Worksheet on Amines
1. C3 C3 C C3 C2C2C3 amine 2. Br C3C2CC2CC3 C2C3-3-hexanamine 3. Br C2C2C3 -aniline
Amines - eterocyclic itrogen Compounds
Amines - Physical Properties 1º amine 2º amine 3º amine 1) Both 1º and 2º amines exhibit strong secondary forces (hydrogen bonding), primary amines slightly more so than secondary amines. 2) ydrogen bonding involving nitrogen atoms is weaker than that involving oxygen atoms because nitrogen is less electronegative than oxygen. a) The secondary forces in primary and secondary amines are weaker than those in alcohols. b) The strength of - hydrogen bonding in amines is comparable to the dipole-dipole forces in aldehydes and ketones.
Amines - Physical Properties 1º amine 2º amine 3º amine 1) Tertiary amines do not possess an - bond and therefore exhibit only weak secondary forces. 2) The strength of the weaker secondary forces in tertiary amines is comparable to those in ethers and hydrocarbons. 3) Tertiary amines have melting and boiling points considerably lower than those of primary and secondary amines, comparable to those of ethers and hydrocarbons.
Amines - Physical Properties
Amines - Physical Properties
Amines - Basic Compounds When dissolved in water, amines generate hydroxide ions. 4 + + 2O =, alkyl, aryl + + O- The product of the reaction is a salt and it is named from the name of the starting amine. C3 methylamine + 2O C3 + O- + a solution of methylammonium hydroxide
Acidities and Basicities of Organic Compounds Values for 0.10 M aqueous solution Compound Structure [O - ] [3O + ] p Ionization (%) sodium hydroxide ao 1.0 x 10-1 1.0 x 10-13 13.00 100 methyl amine C32 6.8 x 10-3 1.5 x 10-12 11.82 6.8 aniline C652 6.5 x 10-6 2.4 x 10-9 8.62 0.0065 water 2O 1.0 x 10-7 1.0 x 10-7 7.00 0.0001 ethanol C3C2O 1.0 x 10-7 1.0 x 10-7 7.00 0.0001 phenol C65O 3.0 x 10-9 3.3 x 10-6 5.48 0.0033 acetic acid C3COO 7.7 x 10-12 1.3 x 10-3 2.89 1.3 benzoic acid C65COO 4.0 x 10-12 2.5 x 10-3 2.60 2.5 hydrochloric acid Cl 1.0 x 10-13 1.0 x 10-1 1.00 100
Amines - Basic Compounds Ammonia may be reacted with a strong acid to quantitatively yield an amonium salt. 3 + Cl 4Cl ammonia hydrogen ammonium chloride chloride An amine may be reacted with a strong acid to quantitatively yield an amine salt. C3 methylamine + Cl C3 Cl- + methylammonium chloride
Amines - Properties of Amine Salts C3 methylamine + Cl C3 + Cl- methylammonium chloride mp -94ºC, bp -6ºC mp 232ºC The melting and boiling points of amine salts are much higher than those of the corresponding amines. All amine salts are solids at room temperature. Amine salts are much more soluble in water than amines due to the strong interaction of water molecules with ions. Amines are soluble in neutral or lower p where they are converted into their salt forms.
Amines - Amine Based Drugs O C 2C2 C 3 Cl - + C3 Clphenylephrine hydrochloride EOSYEPIE 3-(2-(methylamino)ethyl)phenol hydrochloride O C 2 C 3 C O C 2C2 C 2 C 3 Cl C O C 2 C 2 C 3 Cl C 3 2 procaine hydrochloride OVACAIE 2-(diethylamino)ethyl 4-aminobenzoate hydrochloride diphenehydramine hydrochloride BEADYL 2-(benzhydryloxy)-,-dimethylethanamine hydrochloride
Biologically Interesting Amines
Biologically Interesting Amines
Interconversion of Amine Forms Cl Base Cl- + Cocaine (Free Base) Cocaine hydrochloride
Worksheet on Amines
4. C3 C3 C C3 C2C2C3 Cl isopropyl methyl propyl amine
5. C 3 C C 3 2 C 2 Cl ao C 3 dimethylpropyl ammonium chloride
6. C 3 C 2 C 3 C 2 C C 3 2 C 2 C 3 Cl ao