Undergraduate → Organic chemistry → Functional Group ↓
Amin
Introduction to amines
Amines are an important class of organic compounds that are derived from ammonia (NH3) by replacing one or more hydrogen atoms with alkyl or aryl groups. They play important roles in both industrial applications and biological systems. Amines can be classified as primary, secondary, or tertiary depending on the number of organic substituents attached to the nitrogen atom. Primary amines have one substituent, secondary amines have two, and tertiary amines have three substituents. The general formulas for these types of amines are:
Primary amine: RNH2 Secondary amine: R2NH Tertiary amine: R3N
Structures and examples
Primary amine
In primary amines, an alkyl or aryl group is attached to the nitrogen atom. The simplest primary amine is methylamine. The structure of a primary amine is as follows:
H | R - N | H
Examples of primary amines are:
CH3NH2
- methylamineC2H5NH2
- ethylamineC6H5NH2
- aniline
Secondary amine
In secondary amines, two alkyl or aryl groups are bonded to nitrogen. A simple example is dimethylamine:
R | R - N | H
Examples of secondary amines include:
(CH3)2NH
- dimethylamineC2H5NHC2H5
- diethylamineC6H5NHC2H5
- N-ethylaniline
Tertiary amine
Tertiary amines have three alkyl or aryl groups attached to the nitrogen atom. The simplest example is trimethylamine:
R | R - N | R
Examples of tertiary amines include:
(CH3)3N
- trimethylamineC2H5N(C2H5)2
- triethylamineC6H5N(CH3)2
- N,N-dimethylaniline
Physical properties of amines
Amines generally have a fishy odor, which is particularly strong in the case of lower aliphatic amines. They exhibit higher boiling points than alkanes of similar molecular weight, especially in primary and secondary amines, due to the presence of hydrogen bonding. However, compared to alcohols, amines have lower boiling points because nitrogen is less electronegative than oxygen, resulting in weaker hydrogen bonds.
Amines are also known for their solubility in water, which is mainly due to hydrogen bonding with water molecules. Primary and secondary amines are more soluble in water than tertiary amines due to stronger hydrogen bonding ability. Solubility decreases with the increase in the molecular weight of the amines.
Melting and boiling point
The boiling point of amines follows the following trend:
Primary > secondary > tertiary, for same molecular weight
This trend is attributed to the decreasing ability to form intermolecular hydrogen bonds.
Chemical properties of amines
Basicity
Amines are basic in nature due to the lone pair of electrons on the nitrogen atom, which allows them to accept protons. The basic strength of amines is affected by substituents, which can donate electron density to the nitrogen atom or withdraw electron density from it.
In the gaseous state the order of alkalinity is usually:
Primary > secondary > tertiary
However, in aqueous solution the order may change due to the dissolution of hydrogen bonds, often making tertiary amines less basic than secondary amines.
Jet
Nucleophilic substitution
Amines can participate in nucleophilic substitution reactions, where they react with alkyl halides to form substituted amines.
RNH2 + R'X → RR'NH + HX
Reaction with acids
Amines react with acids to form amine salts, which are usually crystalline solids at room temperature.
RNH2 + HCl → RNH3+ Cl-
Hoffman elimination
In the Hofmann elimination process, quaternary ammonium iodide is converted to an alkene and a tertiary amine:
[R4N]+ I- → Alkene + R3N + HI
Commercial importance and applications
Amines are used in the manufacture of dyes, drugs, and polymers. They serve as intermediates in the synthesis of pharmaceuticals and are often used as building blocks in organic synthesis. For example, Aniline
is an important starting material in the production of polyurethane foam and other industrial chemicals.
Biological significance
Many biologically important molecules contain the amine functional group, including amino acids, which are the building blocks of proteins. Amines are also found in neurotransmitters such as dopamine and serotonin, which are important for nerve function in humans and animals.
Summary
In summary, amines are versatile and essential compounds in organic chemistry. They are characterized by their nitrogen-containing functional group and are classified into primary, secondary, and tertiary amines based on their substitution level. Amines are important in a variety of chemical reactions, industrial applications, and biological processes, making them an integral part of both chemical and life sciences.