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R3NH

R3NH is not a single defined compound in standard chemical nomenclature. Instead, it is a generic notation used in organic chemistry to refer to a nitrogen atom bonded to three substituents labeled R and carrying a hydrogen, effectively representing the protonated form of a tertiary amine or the corresponding ammonium fragment in reaction schemes. In practice, when R3NH is written, it often denotes the conjugate acid of a tertiary amine, which formalists write as R3NH+.

Context and usage

In acid–base discussions and reaction mechanisms, R3NH+ appears as an intermediate or counterion. The exact identity

Properties and examples

Because the R groups are variable, properties of R3NH+ salts depend on the specific substituents. Common examples

Preparation

R3NH+ salts are typically prepared by protonating a tertiary amine (R3N) with a Brønsted acid, forming the

See also

Amines, ammonium ions, quaternary ammonium salts, proton transfers, acid-base catalysis.

of
the
R
groups
varies
and
can
be
alkyl
or
aryl
substituents,
leading
to
a
family
of
R3NH+
species
with
different
physical
properties.
The
notation
is
commonly
encountered
in
representations
of
ammonium
salts,
where
the
cation
is
R3NH+
and
the
anion
is
a
counterion
such
as
Cl−,
BF4−,
or
another
inorganic
or
organic
anion.
include
triethylammonium
salts
(R
=
C2H5)
and
trimethylammonium
salts
(R
=
CH3).
These
salts
tend
to
be
polar
and
are
often
soluble
in
water
or
polar
organic
solvents.
The
acidity
of
the
corresponding
amine
precursor
and
the
overall
behavior
of
the
salt
are
governed
by
the
pKa
of
the
conjugate
acid
(R3NH+).
ammonium
cation
(R3NH+)
paired
with
a
suitable
counterion.