Navigation Links
Amine


Ammonia

Amines are organic compounds containing nitrogen as the key atom in the amine functional group. Amines have structures resembling ammonia, where one or more hydrogen atoms are replaced by alkyl groups or other groups where the nitrogen is bonded to a carbon atom in the group (groups symbolized by R below). However, if any of the carbons bonded to the nitrogen is part of a carbonyl group, then the compound is considered an amide rather than an amine.

See the Category:Amines for a list of types of amine and some real examples of this class of chemical.


As shown in the following pictures, if only one the hydrogens in ammonia is replaced by a carbon based group, then it is a primary amine. If two of the hydrogens are replaced by two carbon based groups, then it is a secondary amine. If all three hydrogens are replaced with three carbon based groups, then it is a tertiary amine. Note: the subscripts on the R groups are simply used to label these groups to differentiate them and show that they may be different (or they could be the same). However, the number subscripts on the H atoms show how many H atoms there are in that group.

Primary Amine:
Secondary Amine:
Tertiary Amine:
Contents

Naming

Lower amines are named with the suffix -amine.


Methylamine

Higher amines have the prefix amino as a functional group.


2-amino-pentane
(or better: pent-2-yl-amine or pentane-2-amine)

Properties

Ions of compound Ka (conjugate acid)
Aniline C6H5-NH2 2.0·10-5 M
Ammonia NH3 5.6·10-10 M
Ethylene diamine NH2-CH2-CH2-NH2 1.3·10-10 M
Butylamine CH3-CH2-CH2-CH2-NH2 0.15·10-10 M

Like ammonia, amines act as bases and are reasonably strong (see table for examples of conjugate acid Ka values). The nitrogen atom has a lone electron pair available which can accept a H+ ion to bond to the nitrogen forming a positive substituted ammonium ion. The pairs of dots on the N atoms in the chemical reactions shown in this article represent the lone electron pairs on the nitrogens in the amines. These lone pairs also contribute to the solubility of simple amines due to hydrogen bonding between water molecules and the lone electron pairs.

Also, a halogenoalkane can react with an amine to form a corresponding alkyl-substituted amine, with the release of a halogen acid.

If the reacting amine is a tertiary amine in such a reaction, then a positive quaternary ammonium cation will be formed along with a negative halide ion.

These sort of paired ion compounds are called quaternary ammonium salts. The X shown in the above reactions can also be some other leaving group forming a corresponding acid or anion.

Because inversion of the three substituent groups bonded to the nitrogen of an amine around the nitrogen's lone electron pair is usually possible, the nitrogen in the amine functional group will usually not be a chiral center.

The volatile amines often have fishy smells.

Synthesis

primary amines are firstly produced due to the Gabriel Synthesis.

Reactions

    • Dissolving secondary and tertiary amines using strong acids like HI, HBr, or HCl does not lead to a lower grade amine and an alkylhalide, hence the nitrogen-group is not a preferred leaving group.
    • Because they are basic, amines can neutralize carboxylic acids to form the corresponding substituted ammonium carboxylate salts. Upon heating to 200o C, these salts will dehydrate to form amides, if the initial amine was primary or secondary.
    • Derivatives of carboxylic acids, such as acyl chlorides, can react with primary or secondary amines to form amides.

Aromatic amines

Aromatic amines are amines in which the nitrogen is connected to an aromatic ring as in anilines. The aromatic ring strongly decreases the basicity of the amine, depending on its substituents.

See also


'"/>


(Date:8/28/2014)... is available in German . ... owes its name to a striking pattern of blue stripes ... cells, reflective silvery cells, and yellow cells emerge during growth ... as a multilayered mosaic to compose the characteristic colour pattern. ... types have to interact to form proper stripes, the embryonic ...
(Date:8/28/2014)... (Maximizing Access to Research Careers) Program has announced the ... Genetics from October 18 22, 2014 in San ... the entry of students, post doctorates and scientists from ... community and to encourage the participation of young scientists ... year MARC conferred 16 awards totaling $29,600., The FASEB ...
(Date:8/28/2014)... (August 28, 2014) Researchers at the University of ... muscular dystrophy (FSHD) to be used for muscle regeneration ... potential therapies for FSHD. , The research is published ... Reports . , There is no treatment for FSHD, ... common type of muscular dystrophy. FSHD is an unusual ...
Breaking Biology News(10 mins):How the zebrafish gets its stripes 2How the zebrafish gets its stripes 3UMN researchers find animal model for understudied type of muscular dystrophy 2
... FAIRFAX, Va.For the first time, the Society of ... professional articles about uterine artery embolization, a treatment directed ... adverse health effects that may occur due to the ... and Interventional Radiology "virtual" collection allows health care ...
... Conservation Society announced today that critically endangered alligators in ... WCS,s Bronx Zoo, in partnership with two other North ... Management of the State Forestry Administration of China, has ... multiplying on their own. The alligator hatchlings15 in ...
... is the foundation of the body,s immune response and ... is part of the immune system, and recognizes certain ... HIV. How the molecule binds to pathogens has been ... by University of Illinois chemist Deborah Leckband show that ...
Cached Biology News:Avoiding hysterectomy: Major interventional radiology E-collection info available 2Avoiding hysterectomy: Major interventional radiology E-collection info available 3Reintroduced Chinese alligators now multiplying in the wild in China 2Reintroduced Chinese alligators now multiplying in the wild in China 3Flexible neck in cell-receptor DC-SIGN targets more pathogens 2
Other biology definitionOther Tags