Classification of Amines
Have you ever wondered why toilets smell so bad? Well, ammonia and compounds of ammonia called amines are responsible for that foul smell. These compounds have a pungent smell, but they have an enormous significance in chemistry and our everyday lives. Amines are an essential class of organic compounds. Amines are an exciting subject to study, and it also has a major application in biology. Nitrogen is the only famous product, but many other products of ammonia get derived by changing the hydrogen atoms. In this article, you can learn about the classification of amines, their structure, and their physical properties of amines.
What are Amines?
Amines are organic compounds, deriving from ammonia (NH3). Amines get derived by replacing one or more hydrogen atoms with an alkyl or aryl group. Amines have a nitrogen atom with a lone pair of electrons. When you replace one or more hydrogen atoms with substituent groups like alkyl or aryl in ammonia, you get a new type of organic compound called amines. Amino acids, biogenic amine, trimethylamine, and aniline are some of the important amine structures.
Classification of Amines
Amines get classified into four categories, such as primary, secondary, tertiary, and cyclic. A primary amine is the one where you replace one of the three hydrogen atoms with an alkyl or aryl group. When you replace two of the three hydrogen atoms, then you get a secondary amine. Likewise, by replacing all three hydrogen atoms, tertiary amines get formed.
Keep in mind that only secondary or tertiary amines can be cyclic. Examples of primary amines are CH3NH2, methylamine, CH3NHCH3, and dimethylamine are examples of secondary amines. An example of tertiary amine is trimethylamine and 3 - member ring aziridine is an example of cyclic amine.
Physical Properties of Amines
The following are various amine physical properties that you should know.
General Properties:
Lower aliphatic amine often finds its gaseous state, and they have a fishy smell.
Primary amines having three or four carbon atoms are in the liquid state at room temperatures, and higher ones get found in the solid state.
Aniline and various arylamines are colorless. But, they do get colored due to atmospheric oxidation when you keep them in the open.
Solubility Characteristics:
Lower aliphatic amines can form hydrogen bonds with water molecules. And thus, such amines are soluble in water.
When there is an increase in the hydrophobic alkyl part of the amines, its molar mass goes up. As a result, such amines have a lower solubility in water.
Amines are soluble in organic solvents like alcohol, ether, and benzene because alcohols have high polarity as compared to amines.
Boiling Points of Amines:
Primary and secondary amines get engaged in intermolecular association because of the hydrogen bonding between the nitrogen of one molecule with the hydrogen of another molecule.
Such intermolecular association is more in primary amines as compared to secondary amines because there are two hydrogen atoms present for bond formation.
Tertiary amines don’t have an intermolecular association as they don't have any hydrogen atoms available for hydrogen bond formation.
That’s why the order of boiling points for isomeric amines goes like primary > secondary > tertiary.
Those were some fundamental physical properties of amines.
Amines and Amino Acids
I am sure you must have come across the word"amino acid". It is a compound that is a component of biological proteins. Amines are involved in the formation of amino acids while Amines are compounds that are derived from Ammonia. Amines chapter is studied in organic chemistry and they are basically classified as functional groups or organic nitrogen compounds containing nitrogen atoms with lone pairs of electrons. Many vitamins are made up of amino acids. Serotonin is an important amine that functions as one of the most important neurotransmitters in the brain. Amines are an important class of organic compounds found widely in plants and animals as proteins, vitamins, alkaloids, etc. Amine research is attractive in many ways. Amine chemistry is very important in biology. It is essential for all living things. Amines can be liquids, solids, or gases at room temperature.
Types of Amines
Amines are typically classified into- Aliphatic and Aromatic Amines.
Aliphatic Amines: Aliphatic amines are compounds where the nitrogen atom is directly bonded to one or more alkyl groups.
Aromatic Amines: Aromatic amines are compounds that are attached to aromatic hydrocarbons and have at least one benzene ring.
Aromatic Amines are further classified into-
Aryl amines
Aryl alkyl amines
Further Classification of Amine
Based on the number of alkyl or aryl groups attached to the nitrogen of the amine, further classification is as Primary, Secondary Tertiary, and cyclic.
Primary Amine: When one hydrogen atom in ammonia is replaced with alkyl or aromatic groups, that means it is a primary amine. Some examples of primary alkylamines include amino acids and methylamines, and primary aromatic amines include aniline.
Secondary Amine: Amines with two hydrogen atoms of ammonia are replaced with organic substituents, alkyl, and/or aryl substituents, forming secondary amine. Common examples include dimethylamine. Diphenylamine is also an example of aromatic amines.
Tertiary Amine: Amines are formed when all three hydrogen atoms of ammonia get replaced by organic substituents, Alkyl or aryl groups, forming Tertiary amine. Examples are trimethylamine and EDTA.
Keep in mind that only secondary or tertiary amines can be cyclic. Examples of primary amines are CH3NH2, methylamine, CH3NHCH3, and dimethylamine are examples of secondary amines. An example of tertiary amine is trimethylamine and 3 - member ring aziridine is an example of cyclic amine.
FAQs on Physical Properties of Amines
1. What is the use of Amines?
Amine is used in our daily lives. Available in vitamins, proteins, hormones and alkaloids. Amine is also used in the manufacture of various medicines.
2. State the difference between Amide and Amine?
The fundamental difference between amides and amines in the presence of carbonyl groups. Amines do not have a carbonyl group attached to nitrogen, but amides have a carbonyl group attached to nitrogen.
3. Write the order of boiling point of Isomeric Amines.
The order of boiling point is given as-
Primary> Secondary> Tertiary
4. What is the main difference between Primary Amine and Secondary Amine?
Primary amines have an alkyl or aryl group attached to a nitrogen atom whereas the Secondary amines have two alkyl or aryl groups attached to the nitrogen atom.
5. Do amines react with alcohol?
In general, most alcohols are slightly less acidic than water. Alcohol is a much weaker acid than carboxylic acids and mineral acids do not react with weak bases such as amine and react only weakly with strong bases.
6. What are the types of amines?
Depending on the number of carbon-containing groups attached to the amines, they can either be primary, secondary or tertiary. The amine is primary if it has a single carbon-containing group like CH3NH2. If the amine has two carbon-containing groups, then it becomes secondary, and three groups make it tertiary. Incorporating the lone electron pair of nitrogen, sometimes it gets energetically favoured to use the nitrogen as a nucleophile and therefore, binds a fourth carbon-containing group to the amine. As a result, you get a quaternary ammonium ion. Also, an organic compound with multiple amino groups gets called as a diamine, triamine, tetramine, and so on.
7. Arrange the below compounds in the decreasing order of their boiling points.
a. C2H5OH
b. (CH3)2NH
c. C2H5NH2
1.a > b > c
2. b > a > c
3. c > a > b
4. c > b > a
Here, the correct order is option I. a > b > c. You must note that all the given compounds have intermolecular hydrogen bonding because of which they have high boiling points. Among all, C2H5OH has the strongest hydrogen bonding because O is more electronegative than N in other compounds. That’s why the compound with O has the highest boiling point. In (CH3)2NH and C2H5NH2, the latter one has a longer alkyl chain making the hydrogen bonding even weaker. Therefore, the correct order of decreasing boiling points is a > b > c.