Hydronium

In chemistry, hydronium (hydroxonium in

traditional British English) is the common
+
name for the cation [H3O] , also written as
+
H3O , the type of oxonium ion produced by
protonation of water. It is often viewed as
the positive ion present when an Arrhenius
acid is dissolved in water, as Arrhenius
acid molecules in solution give up a proton
+
(a positive hydrogen ion, H ) to the
surrounding water molecules (H2O). In
fact, acids must be surrounded by more
than a single water molecule in order to
+
ionize, yielding aqueous H and conjugate
base. Three main structures for the
aqueous proton have garnered
experimental support: the Eigen cation,
which is a tetrahydrate, H3O+(H2O)3, the
Zundel cation, which is a symmetric
dihydrate, H+(H2O)2, and the Stoyanov
cation, an expanded Zundel cation, which
is a hexahydrate: H+(H2O)2(H2O)4.[1][2]
Spectroscopic evidence from well-defined
IR spectra overwhelmingly supports the
Stoyanov cation as the predominant
form.[3][4][5][6] For this reason, it has been
suggested that wherever possible, the
symbol H+(aq) should be used instead of
the hydronium ion.[2]

Relation to pH
The molar concentration of hydronium or
+
H ions determines a solution's pH
according to

where M = mol/L. The concentration of

hydroxide ions analogously determines a
solution's pOH. The molecules in pure
water auto-dissociate into aqueous
protons and hydroxide ions in the
following equilibrium:
 Hydronium

Names

IUPAC name
oxonium

Other names
hydronium ion

Identifiers
CAS 13968-
Number
08-6 (htt
ps://com
monche
mistry.ca
s.org/det
ail?cas_r
n=13968-
08-6)

3D Interactive
model
image (htt
(JSmol)
ps://chem
apps.stola
f.edu/jmo
l/jmol.ph
p?model
=%5BOH
 3%2B%5
D)

ChEBI CHEBI:29412
(https://ww
w.ebi.ac.uk/c
hebi/searchI
d.do?chebiId
=29412)

ChemSpi 109935
der (https://
www.che
mspider.
com/Che
mical-Str
ucture.10
9935.ht
ml)
Gmelin 141
Reference

PubChem 123332
CID
(https://p
ubchem.
ncbi.nlm.
nih.gov/c
ompoun
d/12333
2)

CompTox DTXSID208
Dashboard
3597 (http
(EPA)
s://compto
epa.gov/da
hboard/che
mical/deta
 s/DTXSID2
893597)

InChI
InChI=1S/H2O/h1
H2/p+1
Key: XLYOFNOQVP
JJNP-UHFFFA
OYSA-O

SMILES
[OH3+]

Properties

Chemical H3O+
formula

Molar 19.023 g·mol

mass −1

Acidity 0
(pKa)
Conjugat Water
e base

Except where
otherwise noted,
data are given for
materials in their
standard state (at
25 °C [77 °F],
100 kPa).
verify (https://en.w
ikipedia.org/w/inde
x.php?title=Special:
ComparePages&rev
1=417094923&page
2=Hydroniu
m) (what is ?)
Infobox references
 − +
H2O ⇌ OH (aq) + H (aq)

In pure water, there is an equal number of

+
hydroxide and H ions, so it is a neutral
solution. At 25 °C (77 °F), pure water has a
pH of 7 and a pOH of 7 (this varies when
the temperature changes: see self-
ionization of water). A pH value less than 7
indicates an acidic solution, and a pH
value more than 7 indicates a basic
solution.[7]

Nomenclature
According to IUPAC nomenclature of
organic chemistry, the hydronium ion
should be referred to as oxonium.[8]
Hydroxonium may also be used
unambiguously to identify it.

An oxonium ion is any ion with a trivalent

oxygen cation. For example,
trimethyloxonium is an oxonium ion, but
not a hydronium ion.

Structure
+
Since O and N have the same number of
+
electrons, H3O is isoelectronic with
ammonia. As shown in the images above,
+
H3O has a trigonal pyramidal molecular
geometry with the oxygen atom at its
apex. The H−O−H bond angle is
approximately 113°,[9] and the center of
mass is very close to the oxygen atom.
Because the base of the pyramid is made
up of three identical hydrogen atoms, the
+
H3O molecule's symmetric top
configuration is such that it belongs to the
C3v point group. Because of this symmetry
and the fact that it has a dipole moment,
the rotational selection rules are ΔJ = ±1
and ΔK = 0. The transition dipole lies along
the c-axis and, because the negative
charge is localized near the oxygen atom,
the dipole moment points to the apex,
perpendicular to the base plane.
Acids and acidity
The hydrated proton is very acidic: at
25 °C, its pKa is approximately 0.[10] The
values commonly given for pKaaq(H3O+)
are 0 or –1.74. The former uses the
convention that the activity of the solvent
in a dilute solution (in this case, water) is
1, while the latter uses the value of the
concentration of water in the pure liquid of
55.5 M. Silverstein has shown that the
latter value is thermodynamically
unsupportable.[11] The disagreement
comes from the ambiguity that to define
pKa of H3O+ in water, H2O has to act
simultaneously as a solute and the
solvent. The IUPAC has not given an
official definition of pKa that would resolve
this ambiguity. Burgot has argued that
H3O+(aq) + H2O (l) ⇄ H2O (aq) + H3O+ (aq)
is simply not a thermodynamically well-
defined process. For an estimate of
pKaaq(H3O+), Burgot suggests taking the
measured value pKaEtOH(H3O+) = 0.3, the
pKa of H3O+ in ethanol, and applying the
correlation equation pKaaq = pKaEtOH – 1.0
(± 0.3) to convert the ethanol pKa to an
aqueous value, to give a value of
pKaaq(H3O+) = –0.7 (± 0.3).[12] On the other
hand, Silverstein has shown that Ballinger
and Long's experimental results [13]
support a pKa of 0.0 for the aqueous
proton.[14] Neils and Schaertel provide
added arguments for a pKa of 0.0 [15]

The aqueous proton is the most acidic

species that can exist in water (assuming
sufficient water for dissolution): any
stronger acid will ionize and yield a
+
hydrated proton. The acidity of H (aq) is
the implicit standard used to judge the
strength of an acid in water: strong acids
+
must be better proton donors than H (aq),
as otherwise a significant portion of acid
will exist in a non-ionized state (i.e.: a
+
weak acid). Unlike H (aq) in neutral
solutions that result from water's
+
autodissociation, in acidic solutions, H
(aq) is long-lasting and concentrated, in
proportion to the strength of the dissolved
acid.

pH was originally conceived to be a

measure of the hydrogen ion
concentration of aqueous solution.[16]
Virtually all such free protons are quickly
hydrated; acidity of an aqueous solution is
therefore more accurately characterized by
+
its concentration of H (aq). In organic
syntheses, such as acid catalyzed
+
reactions, the hydronium ion (H3O ) is
+
used interchangeably with the H ion;
choosing one over the other has no
significant effect on the mechanism of
reaction.

Solvation
Researchers have yet to fully characterize
the solvation of hydronium ion in water, in
part because many different meanings of
solvation exist. A freezing-point
depression study determined that the
mean hydration ion in cold water is
+
approximately H3O (H2O)6:[17] on average,
each hydronium ion is solvated by 6 water
molecules which are unable to solvate
other solute molecules.
Some hydration structures are quite large:
+
the H3O (H2O)20 magic ion number
structure (called magic number because of
its increased stability with respect to
hydration structures involving a
comparable number of water molecules –
this is a similar usage of the term magic
number as in nuclear physics) might place
the hydronium inside a dodecahedral
cage.[18] However, more recent ab initio
method molecular dynamics simulations
have shown that, on average, the hydrated
proton resides on the surface of the
+
H3O (H2O)20 cluster.[19] Further, several
disparate features of these simulations
agree with their experimental counterparts
suggesting an alternative interpretation of
the experimental results.

Zundel cation

Two other well-known structures are the

Zundel cation and the Eigen cation. The
Eigen solvation structure has the
+
hydronium ion at the center of an H 9O 4
complex in which the hydronium is
strongly hydrogen-bonded to three
neighbouring water molecules.[20] In the
+
Zundel H5O2 complex the proton is shared
equally by two water molecules in a
symmetric hydrogen bond.[21] Recent work
indicates that both of these complexes
represent ideal structures in a more
general hydrogen bond network defect.[22]

Isolation of the hydronium ion monomer in

liquid phase was achieved in a
nonaqueous, low nucleophilicity superacid
solution (HF−SbF5SO2). The ion was
17
characterized by high resolution O
nuclear magnetic resonance.[23]

A 2007 calculation of the enthalpies and

free energies of the various hydrogen
bonds around the hydronium cation in
liquid protonated water[24] at room
temperature and a study of the proton
hopping mechanism using molecular
dynamics showed that the hydrogen-
bonds around the hydronium ion (formed
with the three water ligands in the first
solvation shell of the hydronium) are quite
strong compared to those of bulk water.

A new model was proposed by Stoyanov

based on infrared spectroscopy in which
+
the proton exists as an H13O6 ion. The
positive charge is thus delocalized over 6
water molecules.[25]

Solid hydronium salts

For many strong acids, it is possible to
form crystals of their hydronium salt that
are relatively stable. These salts are
sometimes called acid monohydrates. As a
rule, any acid with an ionization constant
of 109 or higher may do this. Acids whose
ionization constants are below 109
+
generally cannot form stable H3O salts.
For example, nitric acid has an ionization
constant of 101.4, and mixtures with water
at all proportions are liquid at room
temperature. However, perchloric acid has
an ionization constant of 1010, and if liquid
anhydrous perchloric acid and water are
combined in a 1:1 molar ratio, they react to
form solid hydronium perchlorate
+ −
(H3O ·ClO4).
The hydronium ion also forms stable
compounds with the carborane superacid
H(CB11H(CH3)5Br6).[26] X-ray
crystallography shows a C3v symmetry for
the hydronium ion with each proton
interacting with a bromine atom each from
three carborane anions 320 pm apart on
average. The [H3O][H(CB11HCl11)] salt is
also soluble in benzene. In crystals grown
from a benzene solution the solvent co-
crystallizes and a H3O·(C6H6)3 cation is
completely separated from the anion. In
the cation three benzene molecules
surround hydronium forming pi-cation
interactions with the hydrogen atoms. The
closest (non-bonding) approach of the
anion at chlorine to the cation at oxygen is
348 pm.

There are also many known examples of

salts containing hydrated hydronium ions,
+
such as the H5O2 ion in HCl·2H2O, the
+ +
H7O3 and H9O4 ions both found in
HBr·4H2O.[27]

Sulfuric acid is also known to form a

−
hydronium salt H3O+HSO4 at temperatures
below 8.49 °C (47.28 °F).[28]

Interstellar H3 O+

Hydronium is an abundant molecular ion in

the interstellar medium and is found in
diffuse[29] and dense[30] molecular clouds
as well as the plasma tails of comets.[31]
Interstellar sources of hydronium
observations include the regions of
Sagittarius B2, Orion OMC-1, Orion BN–
IRc2, Orion KL, and the comet Hale–Bopp.

Interstellar hydronium is formed by a chain

of reactions started by the ionization of H2
+ +
into H2 by cosmic radiation.[32] H3O can
produce either OH− or H2O through
dissociative recombination reactions,
which occur very quickly even at the low
(≥10 K) temperatures of dense clouds.[33]
This leads to hydronium playing a very
important role in interstellar ion-neutral
chemistry.

Astronomers are especially interested in

determining the abundance of water in
various interstellar climates due to its key
role in the cooling of dense molecular
gases through radiative processes.[34]
However, H2O does not have many
favorable transitions for ground-based
observations.[35] Although observations of
HDO (the deuterated version of water[36])
could potentially be used for estimating
H2O abundances, the ratio of HDO to H2O
is not known very accurately.[35]
Hydronium, on the other hand, has several
transitions that make it a superior
candidate for detection and identification
in a variety of situations.[35] This
information has been used in conjunction
with laboratory measurements of the
+
branching ratios of the various H3O
dissociative recombination reactions[33] to
provide what are believed to be relatively
accurate OH− and H2O abundances
without requiring direct observation of
these species.[37][38]
Interstellar chemistry

+
As mentioned previously, H3O is found in
both diffuse and dense molecular clouds.
By applying the reaction rate constants (α,
β, and γ) corresponding to all of the
currently available characterized reactions
+
involving H3O , it is possible to calculate
k(T) for each of these reactions. By
multiplying these k(T) by the relative
abundances of the products, the relative
rates (in cm3/s) for each reaction at a
given temperature can be determined.
These relative rates can be made in
absolute rates by multiplying them by the
2 [39]
[H2 ] . By assuming T = 10 K for a dense
cloud and T = 50 K for a diffuse cloud, the
results indicate that most dominant
formation and destruction mechanisms
were the same for both cases. It should be
mentioned that the relative abundances
used in these calculations correspond to
TMC-1, a dense molecular cloud, and that
the calculated relative rates are therefore
expected to be more accurate at T = 10 K.
The three fastest formation and
destruction mechanisms are listed in the
table below, along with their relative rates.
Note that the rates of these six reactions
are such that they make up approximately
99% of hydronium ion's chemical
interactions under these conditions.[31] All
three destruction mechanisms in the table
below are classified as dissociative
recombination reactions.[40]

+
Primary reaction pathways of H3O in
the interstellar medium (specifically,
dense clouds).

Relative rate (cm3/s)

Reaction Type
at 10 K at 50 K
+ +
H2 + H2O → H3O + H Formation 2.97 × 10−22 2.97 × 10−22
+ +
H2O + HCO → CO + H3O Formation 4.52 × 10−23 4.52 × 10−23
+
H+3 + H2O → H3O + H2 Formation 3.75 × 10−23 3.75 × 10−23
+
H3O + e− → OH + H + H Destruction 2.27 × 10−22 1.02 × 10−22
+
H3O + e− → H2O + H Destruction 9.52 × 10−23 4.26 × 10−23
+
H3O + e− → OH + H2 Destruction 5.31 × 10−23 2.37 × 10−23

It is also worth noting that the relative

rates for the formation reactions in the
table above are the same for a given
reaction at both temperatures. This is due
to the reaction rate constants for these
reactions having β and γ constants of 0,
resulting in k = α which is independent of
temperature.

Since all three of these reactions produce

either H2O or OH, these results reinforce
the strong connection between their
+
relative abundances and that of H3O . The
rates of these six reactions are such that
they make up approximately 99% of
hydronium ion's chemical interactions
under these conditions.
Astronomical detections

As early as 1973 and before the first

interstellar detection, chemical models of
the interstellar medium (the first
corresponding to a dense cloud) predicted
that hydronium was an abundant
molecular ion and that it played an
important role in ion-neutral chemistry.[41]
However, before an astronomical search
could be underway there was still the
matter of determining hydronium's
spectroscopic features in the gas phase,
which at this point were unknown. The first
studies of these characteristics came in
1977,[42] which was followed by other,
higher resolution spectroscopy
experiments. Once several lines had been
identified in the laboratory, the first
interstellar detection of H3O+ was made by
two groups almost simultaneously in
1986.[30][35] The first, published in June
vt −
1986, reported observation of the JK = 11
+
− 21 transition at 307 192.41 MHz in
OMC-1 and Sgr B2. The second, published
in August, reported observation of the
same transition toward the Orion-KL
nebula.

These first detections have been followed

by observations of a number of additional
+
H3O transitions. The first observations of
each subsequent transition detection are
given below in chronological order:

+ −
In 1991, the 32 − 22 transition at
364 797.427 MHz was observed in OMC-1
+ −
and Sgr B2.[43] One year later, the 30 − 20
transition at 396 272.412 MHz was
observed in several regions, the clearest of
which was the W3 IRS 5 cloud.[38]

− +
The first far-IR 43 − 33 transition at
69.524 µm (4.3121 THz) was made in
1996 near Orion BN-IRc2.[44] In 2001, three
+
additional transitions of H3O in were
−
observed in the far infrared in Sgr B2; 21
+
− 11 transition at 100.577 µm (2.98073
 − +
THz), 11− 11 at 181.054 µm (1.65582
− +
THz) and 20 − 10 at 100.869 µm (2.9721
THz).[45]

See also
Hydron (hydrogen cation)
Hydride
Hydrogen anion
Hydrogen ion
Grotthus mechanism
Trifluorooxonium
Law of dilution

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External links
J Phys Chem infrared spectra of
hydronium (https://pubs.acs.org/doi/ab
s/10.1021/j100372a014?journalCode=jp
chax)
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