Amine Basicity
Amines
- Amines can be thought of as derivatives of ammonia, in which one or more of the hydrogens is replaced by an alkyl or aryl group
- The number of substituted hydrogens is the basis of classifying amines
Classification of amines
- Notice the classification is not the same as in alcohols and haloalkanes, where the designation primary, secondary and tertiary is based on the substituents on the carbon atom rather than the nitrogen atom
- If the R group is an alkyl group (methyl, ethyl, etc) then then it is an aliphatic amine; if it is an aryl group (benzene ring or phenyl) then it is an aromatic amine
- Aliphatic and aromatic amines share similar chemical reactions and the aryl group can strongly influence the chemistry and reactivity of the amine group
Naming Amines
- Amines can be named using common names or IUPAC systematic names
- The common way to name amines is to use the alkyl (or aryl) prefix followed by -amine
- The IUPAC systematic name uses the numbered prefix amino- followed by the alkane (or aromatic) stem
Nomenclature of aliphatic and aromatic amines table
Basic properties
- The nitrogen atom in ammonia and amine molecules can accept a proton (H+ ion)
- They can therefore act as bases in aqueous solutions by donating its lone pair of electrons to a proton and form a dative bond
- For example, ammonia undergoes an acid-base reaction with dilute hydrochloric acid (HCl) to form a salt
NH3 + HCl → NH4+Cl-
base acid salt
- Amines react with HCl to form amine salts, such as ethylammonium chloride
C2H5NH2 + HCl → C2H5NH3+Cl-
base acid salt
- Like ammonium salts, amine salts are soluble ionic compounds, so when the alkyl group is small they are water soluble but become less so as the carbon chain increases
- We can show the reaction in Brønsted-Lowry terms, where ammonia or the amine acts as a proton acceptor:
The nitrogen atom in ammonia and amines can donate its lone pair of electrons to form a bond with a proton and therefore act as a base
