In chemistry, the hydron, informally called proton, is the cationic form of atomic hydrogen, represented with the symbol H+
. The general term "hydron", endorsed by IUPAC, encompasses cations of hydrogen regardless of isotope: thus it refers collectively to protons (1H+) for the protium isotope, deuterons (2H+ or D+) for the deuterium isotope, and tritons (3H+ or T+) for the tritium isotope.
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| Systematic IUPAC name Hydron (substitutive) Hydrogen(1+) (additive) | |
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| Properties | |
| H+ | |
| Molar mass | 1.007 g·mol−1 |
| Thermochemistry | |
Std molar entropy (S⦵298) | 108.95 J K−1 mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references | |
Unlike most other ions, the hydron consists only of a bare atomic nucleus. The negatively charged counterpart of the hydron is the hydride anion, H−
.
Properties
Solute properties
Other things being equal, compounds that readily donate hydrons (Brønsted acids, see below) are generally polar, hydrophilic solutes and are often soluble in solvents with high relative static permittivity (dielectric constants). Examples include organic acids like acetic acid (CH3COOH) or methanesulfonic acid (CH3SO3H). However, large nonpolar portions of the molecule may attenuate these properties. Thus, as a result of its alkyl chain, octanoic acid (C7H15COOH) is considerably less hydrophilic compared to acetic acid.
The unsolvated hydron (a completely free or "naked" hydrogen atomic nucleus) does not exist in the condensed (liquid or solid) phase. As the surface Electric field strength is inverse to the radius, a tiny nucleus interacts thousands times stronger with nearby electrons than any partly ionized atom.
Although superacids are sometimes said to owe their extraordinary hydron-donating power to the presence of "free hydrons", such a statement is misleading: even for a source of "free hydrons" like H
2F+
, one of the superacidic cations present in the superacid fluoroantimonic acid (HF:SbF5), detachment of a free H+
still comes at an enormous energetic penalty on the order of several hundred kcal/mol. This effectively rules out the possibility of the free hydron being present in solution. For this reason, in liquid strong acids, hydrons are believed to diffuse by sequential transfer from one molecule to the next along a network of hydrogen bonds through what is known as the Grotthuss mechanism.
Acidity
The hydron ion can incorporate an electron pair from a Lewis base into the molecule by adduction:
- [H]+
+ :L → [HL]+
Because of this capture of the Lewis base (L), the hydron ion has Lewis acidic character. In terms of Hard/Soft Acid Base (HSAB) theory, the bare hydron is an infinitely hard Lewis acid.
The hydron plays a central role in Brønsted–Lowry acid–base theory: a species that behaves as a hydron donor in a reaction is known as the Brønsted acid, while the species accepting the hydron is known as the Brønsted base. In the generic acid–base reaction shown below, HA is the acid, while B (shown with a lone pair) is the base:
- HA + :B → [HB]+
+ :A–
The hydrated form of the hydrogen cation, the hydronium (hydroxonium) ion H
3O+
(aq), is a key object of Arrhenius' definition of acid. Other hydrated forms, the Zundel cation H
5O+
2, which is formed from a proton and two water molecules, and the Eigen cation H
9O+
4, which is formed from a hydronium ion and three water molecules, are theorized to play an important role in the diffusion of protons though an aqueous solution according to the Grotthuss mechanism. Although the ion H
3O+
(aq) is often shown in introductory textbooks to emphasize that the hydron is never present as an unsolvated species in aqueous solution, it is somewhat misleading, as it oversimplifies infamously complex speciation of the solvated proton in water; the notation H+
(aq) is often preferred, since it conveys aqueous solvation while remaining noncommittal with respect to the number of water molecules involved.
Isotopes of hydron
- Proton, having the symbol p or 1H+, is the +1 ion of protium, 1H.
- Deuteron, having the symbol 2H+ or D+, is the +1 ion of deuterium, 2H or D.
- Triton, having the symbol 3H+ or T+, is the +1 ion of tritium, 3H or T.
Other isotopes of hydrogen are too unstable to be relevant in chemistry.
History of the term
The term "hydron" is recommended by IUPAC to be used instead of "proton" if no distinction is made between the isotopes proton, deuteron and triton, all found in naturally occurring isotope mixtures. The name "proton" refers to isotopically pure 1H+. On the other hand, calling the hydron simply hydrogen ion is not recommended because hydrogen anions also exist.
The term "hydron" was defined by IUPAC in 1988. Traditionally, the term "proton" was and is[citation needed] used in place of "hydron". The latter term is generally only used in the context where comparisons between the various isotopes of hydrogen is important (as in the kinetic isotope effect or hydrogen isotopic labeling). Otherwise, referring to hydrons as protons is still considered acceptable, for example in such terms as protonation, deprotonation, proton pump, or proton channel. The transfer of H+
in an acid-base reaction is usually referred to as proton transfer. Acid and bases are referred to as proton donors and acceptors correspondingly.
99.9844% of natural hydrons (hydrogen nuclei) are protons, and the remainder (about 156 per million in sea water) are deuterons (see deuterium), except for some very rare natural tritons (see tritium).
See also
- Deprotonation
- Dihydrogen cation
- Hydrogen ion cluster
- Solvated electron
- Superacid
- Trihydrogen cation
References
- "hydron (CHEBI:15378)". Chemical Entities of Biological Interest (ChEBI). UK: European Bioinformatics Institute.
- Bunnet, J.F.; Jones, R.A.Y. (1968). "Names for hydrogen atoms, ions, and groups, and for reactions involving them (Recommendations 1988)" (PDF). Pure Appl. Chem. 60 (7): 1115–6. doi:10.1351/pac198860071115.
[T]he word proton is used not only for the 1H+ ion but commonly, and incorrectly, for H+ in natural abundance. In many contexts this creates no ambiguity and it is likely that this usage will continue.
- [1] Archived 2011-09-27 at the Wayback Machine Computer modeling of proton-hopping in superacids.
- Nomenclature of Inorganic Chemistry-IUPAC Recommendations 2005 [2] IR-3.3.2, p.48
- Compendium of Chemical Terminology, 2nd edition McNaught, A.D. and Wilkinson, A. Blackwell Science, 1997 ISBN 0-86542-684-8, also online Archived 2005-12-12 at the Wayback Machine
- IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "hydron". doi:10.1351/goldbook.H02904
- Bunnet, J.F.; Jones, R.A.Y. (1988). "Names for hydrogen atoms, ions, and groups, and for reactions involving them (Recommendations 1988)" (PDF). Pure Appl. Chem. 60 (7): 1115–6. doi:10.1351/pac198860071115.
In chemistry the hydron informally called proton is the cationic form of atomic hydrogen represented with the symbol H The general term hydron endorsed by IUPAC encompasses cations of hydrogen regardless of isotope thus it refers collectively to protons 1H for the protium isotope deuterons 2H or D for the deuterium isotope and tritons 3H or T for the tritium isotope Hydron NamesSystematic IUPAC name Hydron substitutive Hydrogen 1 additive Other names ProtonIdentifiersCAS Number 12408 02 5 Y3D model JSmol Interactive imageChEBI CHEBI 15378ChemSpider 1010 YIUPHAR BPS 2346KEGG C00080 YPubChem CID 1038UNII 5046UKT60S YCompTox Dashboard EPA DTXSID50924722InChI InChI 1S p 1 YKey GPRLSGONYQIRFK UHFFFAOYSA N YSMILES H PropertiesChemical formula H Molar mass 1 007 g mol 1ThermochemistryStd molar entropy S 298 108 95 J K 1 mol 1Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox references Unlike most other ions the hydron consists only of a bare atomic nucleus The negatively charged counterpart of the hydron is the hydride anion H PropertiesSolute properties Other things being equal compounds that readily donate hydrons Bronsted acids see below are generally polar hydrophilic solutes and are often soluble in solvents with high relative static permittivity dielectric constants Examples include organic acids like acetic acid CH3COOH or methanesulfonic acid CH3SO3H However large nonpolar portions of the molecule may attenuate these properties Thus as a result of its alkyl chain octanoic acid C7H15COOH is considerably less hydrophilic compared to acetic acid The unsolvated hydron a completely free or naked hydrogen atomic nucleus does not exist in the condensed liquid or solid phase As the surface Electric field strength is inverse to the radius a tiny nucleus interacts thousands times stronger with nearby electrons than any partly ionized atom Although superacids are sometimes said to owe their extraordinary hydron donating power to the presence of free hydrons such a statement is misleading even for a source of free hydrons like H2 F one of the superacidic cations present in the superacid fluoroantimonic acid HF SbF5 detachment of a free H still comes at an enormous energetic penalty on the order of several hundred kcal mol This effectively rules out the possibility of the free hydron being present in solution For this reason in liquid strong acids hydrons are believed to diffuse by sequential transfer from one molecule to the next along a network of hydrogen bonds through what is known as the Grotthuss mechanism Acidity The hydron ion can incorporate an electron pair from a Lewis base into the molecule by adduction H L HL Because of this capture of the Lewis base L the hydron ion has Lewis acidic character In terms of Hard Soft Acid Base HSAB theory the bare hydron is an infinitely hard Lewis acid The hydron plays a central role in Bronsted Lowry acid base theory a species that behaves as a hydron donor in a reaction is known as the Bronsted acid while the species accepting the hydron is known as the Bronsted base In the generic acid base reaction shown below HA is the acid while B shown with a lone pair is the base HA B HB A The hydrated form of the hydrogen cation the hydronium hydroxonium ion H3 O aq is a key object of Arrhenius definition of acid Other hydrated forms the Zundel cation H5 O 2 which is formed from a proton and two water molecules and the Eigen cation H9 O 4 which is formed from a hydronium ion and three water molecules are theorized to play an important role in the diffusion of protons though an aqueous solution according to the Grotthuss mechanism Although the ion H3 O aq is often shown in introductory textbooks to emphasize that the hydron is never present as an unsolvated species in aqueous solution it is somewhat misleading as it oversimplifies infamously complex speciation of the solvated proton in water the notation H aq is often preferred since it conveys aqueous solvation while remaining noncommittal with respect to the number of water molecules involved Isotopes of hydronProton having the symbol p or 1H is the 1 ion of protium 1H Deuteron having the symbol 2H or D is the 1 ion of deuterium 2H or D Triton having the symbol 3H or T is the 1 ion of tritium 3H or T Other isotopes of hydrogen are too unstable to be relevant in chemistry History of the termThe term hydron is recommended by IUPAC to be used instead of proton if no distinction is made between the isotopes proton deuteron and triton all found in naturally occurring isotope mixtures The name proton refers to isotopically pure 1H On the other hand calling the hydron simply hydrogen ion is not recommended because hydrogen anions also exist The term hydron was defined by IUPAC in 1988 Traditionally the term proton was and is citation needed used in place of hydron The latter term is generally only used in the context where comparisons between the various isotopes of hydrogen is important as in the kinetic isotope effect or hydrogen isotopic labeling Otherwise referring to hydrons as protons is still considered acceptable for example in such terms as protonation deprotonation proton pump or proton channel The transfer of H in an acid base reaction is usually referred to as proton transfer Acid and bases are referred to as proton donors and acceptors correspondingly 99 9844 of natural hydrons hydrogen nuclei are protons and the remainder about 156 per million in sea water are deuterons see deuterium except for some very rare natural tritons see tritium See alsoDeprotonation Dihydrogen cation Hydrogen ion cluster Solvated electron Superacid Trihydrogen cationReferences hydron CHEBI 15378 Chemical Entities of Biological Interest ChEBI UK European Bioinformatics Institute Bunnet J F Jones R A Y 1968 Names for hydrogen atoms ions and groups and for reactions involving them Recommendations 1988 PDF Pure Appl Chem 60 7 1115 6 doi 10 1351 pac198860071115 T he word proton is used not only for the 1H ion but commonly and incorrectly for H in natural abundance In many contexts this creates no ambiguity and it is likely that this usage will continue 1 Archived 2011 09 27 at the Wayback Machine Computer modeling of proton hopping in superacids Nomenclature of Inorganic Chemistry IUPAC Recommendations 2005 2 IR 3 3 2 p 48 Compendium of Chemical Terminology 2nd edition McNaught A D and Wilkinson A Blackwell Science 1997 ISBN 0 86542 684 8 also online Archived 2005 12 12 at the Wayback Machine IUPAC Compendium of Chemical Terminology 2nd ed the Gold Book 1997 Online corrected version 2006 hydron doi 10 1351 goldbook H02904 Bunnet J F Jones R A Y 1988 Names for hydrogen atoms ions and groups and for reactions involving them Recommendations 1988 PDF Pure Appl Chem 60 7 1115 6 doi 10 1351 pac198860071115
