Base Properties (Oxford AQA International A Level Chemistry)
Revision Note
Written by: Philippa Platt
Reviewed by: Stewart Hird
Base Properties of Amines
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:
Ammonia acting as a Brønsted-Lowry base
Strength of ammonia and amines as bases
The strength of amines depends on the ability of the lone pair of electrons on the nitrogen atom to accept a proton and form a dative covalent bond
The more readily a proton is attracted, the stronger the base is
Factors that may affect the basicity of amines include:
Positive inductive effect - Some groups such as alkyl groups donate electron density to the nitrogen atom causing the lone pair of electrons to become more available and therefore increasing the amine’s basicity
Delocalisation - The presence of aromatic rings such as the benzene ring causes the lone pair of electrons on the nitrogen atom to be delocalised into the benzene ring
The lone pair becomes less available to form a dative covalent bond with ammonia and hence decreases the amine’s basicity
Ethylamine is more basic than phenylamine
Decreasing base strength from ethylamine to phenylamine
Examiner Tips and Tricks
Amines have a fishy smell, which disappears as soon as you add an acid, because you are making an non-volatile salt. Decomposing fish give off amines which are produced by the bacterial decomposition of proteins.
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