Amines

Acid Reflux
• Sometimes acid produced by your stomach can move up into

your oesophagus.
• This can cause symptoms such as a burning chest pain
called heartburn.
• Zantac, Tums and Pepcid are all compounds that contain several
nitrogen atoms, which are important for the function of these
drugs.
Alkaloids
• Naturally occurring amines isolated from plants are called
alkaloids.
Amines in Neurochemistry
Amines in Pharmaceuticals
Amines
• Amines are derivatives of ammonia in which one or more
hydrogens are replaced with alkyl or aryl groups.
• Amines are classified as primary, secondary, or tertiary, depending
on the number of carbon atoms bonded directly to nitrogen.
Aliphatic and Aromatic Amines
• Amines are further divided into aliphatic and aromatic amines.
• In an aliphatic amine, all carbons bonded to nitrogen are derived
from alkyl groups while in an aromatic amine, one or more of the
groups bonded to nitrogen are aryl groups.
Aliphatic amines
Heterocyclic Amines
• An amine in which the nitrogen atom is part of a ring is classified as
a heterocyclic amine.
• When the nitrogen is part of an aromatic ring, the amine is
classified as a heterocyclic aromatic amine.
Aliphatic and Aromatic Amines
Q. Classify each amino group in these alkaloids according to type
(primary, secondary, tertiary, aliphatic, aromatic, heterocyclic).
Nomenclature of Amines
Nomenclature of Primary Amines

• A primary amine is a compound containing an NH2 group
connected to a single alkyl group.
• Two different methods of nomenclature depending on the
complexity of the substituent group.
Method 1
• If the alkyl group is simple, then the compound is generally named
as an alkyl amine.
• The alkyl substituent is identified followed by the suffix “amine”.
Method 2
• Primary amines containing more complex alkyl groups are
generally named as alkanamines.
• The amine is named much like an alcohol, where the suffix -amine
is used in place of -ol.
• The parent chain is numbered starting with the side that is closer to
the functional group.
• When a functional group of higher priority is present, the amino
functional group is listed as a substituent.
• NOTE: Amino functional group has lower priority than hydroxyl
functional group, but higher than halogens.
OH
NH2
C=C
Alkyl, ether, halogen, Ar
Exercise
Q. Write systematic names for these amines.
Q. Write structural formulas for these amines.

(a) 2-Methyl-1-propanamine
(b) Cyclohexanamine
(c) 2-Butanamine
Nomenclature of Primary Aromatic Amines
• Aromatic amines, also called aryl amines, are generally named as
derivatives of aniline.
Nomenclature of Secondary and Tertiary Amines
• Secondary and tertiary amines can also be named as alkyl amines
or as alkanamines, depending on the complexity of the alkyl
substituents.
• If all alkyl groups are rather simple in structure, then the groups
are listed in alphabetical order.
Nomenclature of Secondary and Tertiary Amines
• If one of the alkyl groups is complex, then the compound is
typically named as an alkanamine.
• The most complex alkyl group is treated as the parent and the
simpler alkyl groups treated as substituents.
OH
NH2
C=C, C≡C
Alkyl, ether, halogen, Ar
Exercise
Q. Assign an IUPAC name for each of the following compounds:
Ammonium Salts
• When four atoms or groups of atoms are bonded to a nitrogen
atom, the compound is named as a salt of the corresponding
amine.
• The ending -amine (or -aniline, pyridine, and so on) is replaced
with -ammonium (or anilinium, pyridinium, and so on), and the
name of the anion is added.
• An ion containing a nitrogen atom bonded to any combination of
four alkyl or aryl groups is classified as a quaternary (4°)
ammonium ion.
• Compounds containing such ions have properties characteristic of
salts.
Ammonium Salts
Properties of Amines
Geometry
The nitrogen atom exhibits trigonal pyramidal geometry, with bond
angles of 108°. The C-N bond lengths are 147 pm, which is shorter
than the average C-C bond of an alkane (153 pm) and longer than the
average C-O bond of an alcohol (143 pm).
Colligative properties
Amines exhibit solubility trends that are similar to the trends
exhibited by alcohols.
Amines with a shorter carbon chain will be more soluble in water
than those with longer carbon chains. (Recall explanation for
alcohols)
Consider the following compounds:
Primary and secondary amines can form intermolecular H-bonds.

They typically have higher boiling points than analogous alkanes but
lower boiling points than analogous alcohols.
Consider the following compounds:
The boiling point of amines increases as a function of their capacity

to form hydrogen bonds.
Primary amines typically have higher boiling points, while tertiary
amines have lower boiling points.
• Amines with low molecular weights, such as trimethylamine,
typically have a fishlike odor.
• They are also present in urine, contributing to its characteristic
odor.
• Example, the odor of fish is caused by amines that are produced
when enzymes break down certain fish proteins. Putrescine and
cadaverine are examples of compounds present in rotting fish.
Basicity of Amines
• Amines are generally stronger bases than alcohols or ethers, and
they can be effectively protonated even by weak acids.
Basicity of Amines
Aliphatic Amines
• All aliphatic amines have about the same base strength, pKa of the
conjugate acid 10–11, and are slightly stronger bases than ammonia.
• The increase in basicity compared with ammonia can be attributed
to the greater stability of an alkylammonium ion.
• The greater stability arises from the electron-releasing effect of
alkyl groups.
Basicity of Amines
Aromatic Amines
Aromatic amines are considerably weaker bases than aliphatic
amines.
Compare the pKa values for aniline and cyclohexylamine.
Basicity of Amines
• The resonance stabilization of the free base form of aromatic
amines contribute to the lower basicity of aromatic amines.

Amines

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Acid Reflux

• Sometimes acid produced by your stomach can move up into

Nomenclature of Primary Amines

Q. Write structural formulas for these amines.

Primary and secondary amines can form intermolecular H-bonds.

The boiling point of amines increases as a function of their capacity

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