Sulfhydryl Group

The sulfhydryl group is a group with a sulfur and hydrogen atom. It is also called a thiol,
sulfanyl group, or mercapto. What is a thiol or sulfhydryl? It is a functional group (like an
alcohol, ketone, or amine) found in organic compounds. The sulfur in a sulfhydryl group is
attached to a hydrogen and a carbon (R group). It is classified as an organosulfur compound.
Organosulfur compounds are any organic compound that also contains sulfur. Besides the
sulfhydryl group, organosulfur compounds also include sulfides, disulfides, and thioesters.

An organosulfur group is any organic compound that includes a sulfur.

These other organosulfur compounds all contain sulfur. All of the sulfur atoms are bonded to
carbon for at least one of the bonds, just as with thiols. The difference is that the second bond
is hydrogen for the thiol group. The other organosulfur compounds have that second bond as
carbon, sulfur, or other compounds.

Sometimes the hydrogen can be removed from the thiol (when it acts as an acid, donating a
proton) and put a negative charge on the sulfur. This is a slightly modified sulfhydryl group
called an ionized thiol or ionized sulfhydryl.

Sulfhydryl compounds are named with the suffix thiol. The R-group has the final 'e' dropped in
the name, but this is not the case with naming sulfhydryl compounds. So, a sulfhydryl
compound that comes at the end of methane would be called methanethiol. Furthermore, a
sulfhydryl compound that comes at the end of a methylpropane would be methylpropanethiol.
The position of the thiol does not need to be identified because it always comes at the end of
the chain.

Sulfhydryl Formula
The basic sulfhydryl formula is R-SH. The R is any carbon chain (it can be as simple as a
CH3CH3 or contain many carbon atoms attached to more functional groups). If the R is a
methyl group (CH3CH3), then the formula for the sulfhydryl will be CH3SHCH3SH.

Sulfur is similar to oxygen in how it bonds with other compounds. It prefers to have two bonds,
leaving two lone pairs without bonds. This is the structure that gives it no charge. If an
additional bond is formed, sulfur will have a positive charge. If only one bond is formed, sulfur
will have a negative charge.

Sulfhydryl Structure
The sulfhydryl structure is similar to the functional group alcohol. An alcohol functional group
has the general structure R-OH. Since sulfur and oxygen act in similar ways, it makes sense that
a thiol and alcohol will also act in similar ways. Since sulfur is more electronegative than oxygen
(because it is larger than oxygen), it can give up its hydrogen and have a negative charge.

The general R-SH formula of a sulfhydryl has the structure:

A sulfhydryl or thiol consists of any R group attached to an SH group.

The sulfur has two sets of lone pairs:

The sulfur on a thiol has two sets of lone pairs and no charge.
Properties of Sulfhydryl Group
Compounds containing the sulfhydryl group share common properties. These properties
include:

 Appearance: Generally a liquid at room temperature

 Odor: strong, pungent smell (like a skunk or rotten eggs)
 Polarity: slight polarity
 Boiling point: lower than molecules with a similar molecular weight
 Solubility: low solubility in water

Sulfhydryl is less polar than alcohols because sulfur and hydrogen have a lower dipole moment
than oxygen and hydrogen. It is still a bent molecule and slightly polar, but not as polar as
alcohols. This lower polarity results in many of the properties of thiols. Some of these
properties include a lower boiling point, a liquid at room temperature, and low solubility in
water. The strong, pungent smell comes from the sulfur.

Sulfhydryl Examples
Compounds containing a sulfhydryl are found in many different structures. Sulfhydryl examples
include:

 Methanethiol
 Ethanethiol
 Coenzyme A
 Glutathione
 Cysteine
 Thiamin (vitamin B1)

These thiol examples range from simple compounds, such as methanethiol (with the formula
CH3SHCH3SH to more complex ones such as coenzyme A. The structures of these all contain
the SH group somewhere on the molecule:

Thiols, or sulfhydryl groups, all contain an SH somewhere on the molecule.

Uses of Sulfhydryl Group
Compounds containing the sulfhydryl group have a variety of applications. These compounds
have common biological, pharmaceutical, and industrial uses. Industrial uses of sulfhydryl
groups include using the strong offensive odor to mix in with compounds such as natural gas.
Natural gas does not normally have a strong smell. It can be dangerous when natural gas leaks
into areas where people can inhale it. Sulfhydryl compounds are often mixed with natural gas
to help quickly identify natural gas leaks. The sulfhydryl's strong, unpleasant odor allows any
natural gas leaks to be quickly noticed.

Biological uses include Vitamin B1 (thiamin), cofactors such as coenzyme A, and cysteine (an
amino acid). The body uses thiamin to help break down carbohydrates for energy. It also assists
with heart, muscles, and nerve functions. Coenzyme A helps break down fat in the body so it
can be used for energy. Cysteine is an amino acid. It is part of the building blocks of muscles in
the body.

Many medications have sulfhydryl groups. These include:

 Sodium aurothiomalate to treat arthritis

  Succimer to treat heavy metal poisoning
 Mercaptopurine to treat some forms of cancer

The characteristic smell of skunk spray comes from the sulfhydryl group. Different varieties of
skunks utilize slightly different compounds, but they all contain a sulfhydryl group.

Lesson Summary
The sulfhydryl group is a functional group that contains a sulfur-hydrogen bond. It is part of
the organosulfur compounds or organic compounds that contain sulfur. The general formula
for a sulfhydryl is R-SH. The R group can be any carbon chain, where one of the endings of the
chain is a sulfur-hydrogen. Properties of sulfhydryl groups include:

 Strong, unpleasant odor

 Low boiling point
 Slight polarity
 Low solubility in water

Compounds containing a sulfhydryl group include vitamin B1, coenzyme A, and methanethiol.
These compounds are used to make natural gas smell bad and help the body function properly.
They are also included as medications to treat diseases.