Hydrogen cation

• Formula: H⁺
• Molecular weight: 1.00739
• IUPAC Standard InChI: InChI=1S/p+1 Copy

  
• IUPAC Standard InChIKey: GPRLSGONYQIRFK-UHFFFAOYSA-N Copy
• CAS Registry Number: 12408-02-5
• Chemical structure:
  This structure is also available as a 2d Mol file
• Isotopologues:
  • Deuterium cation
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Reaction thermochemistry data (reactions 251 to 300)
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Reaction thermochemistry data: reactions 1 to 50, reactions 51 to 100, reactions 101 to 150, reactions 151 to 200, reactions 201 to 250, reactions 301 to 350, reactions 351 to 400, reactions 401 to 450, reactions 451 to 500, reactions 501 to 550, reactions 551 to 600, reactions 601 to 650, reactions 651 to 700, reactions 701 to 750, reactions 751 to 800, reactions 801 to 850, reactions 851 to 900, reactions 901 to 950, reactions 951 to 1000, reactions 1001 to 1050, reactions 1051 to 1100, reactions 1101 to 1150, reactions 1151 to 1200, reactions 1201 to 1250, reactions 1251 to 1300, reactions 1301 to 1350, reactions 1351 to 1375
  • Gas phase ion energetics data
• Options:
  • Switch to SI units

Reaction thermochemistry data

Go To: Top, References, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: John E. Bartmess

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.

Reactions 251 to 300

C₆H₆BrO₂^- +  = C₆H₇BrO₂

By formula: C₆H₆BrO₂^- + H⁺ = C₆H₇BrO₂

C₂H₅S^- +  =

By formula: C₂H₅S^- + H⁺ = C₂H₆S

C₇H₉O₂^- +  = C₇H₁₀O₂

By formula: C₇H₉O₂^- + H⁺ = C₇H₁₀O₂

C₁₂H₁₁O₂^- +  = C₁₂H₁₂O₂

By formula: C₁₂H₁₁O₂^- + H⁺ = C₁₂H₁₂O₂

C₈H₉O₄^- +  = C₈H₁₀O₄

By formula: C₈H₉O₄^- + H⁺ = C₈H₁₀O₄

C₇H₆NO₂^- +  = C₇H₇NO₂

By formula: C₇H₆NO₂^- + H⁺ = C₇H₇NO₂

C₆H₆NO₄^- +  = C₆H₇NO₄

By formula: C₆H₆NO₄^- + H⁺ = C₆H₇NO₄

C₄H₅O^- +  =

By formula: C₄H₅O^- + H⁺ = C₄H₆O

O^- +  =

By formula: O^- + H⁺ = HO

C₂H₂FO^- +  =

By formula: C₂H₂FO^- + H⁺ = C₂H₃FO

C₇H₄N^- +  =

By formula: C₇H₄N^- + H⁺ = C₇H₅N

 +  =

By formula: C₉H₆N^- + H⁺ = C₉H₇N

HN₂O₂^- +  =

By formula: HN₂O₂^- + H⁺ = H₂N₂O₂

C₆H₇^- +  =

By formula: C₆H₇^- + H⁺ = C₆H₈

C₃H₁₁BN^- +  =

By formula: C₃H₁₁BN^- + H⁺ = C₃H₁₂BN

C₈H₉^- +  =

By formula: C₈H₉^- + H⁺ = C₈H₁₀

C₁₃H₁₂NO₅^- +  = C₁₃H₁₃NO₅

By formula: C₁₃H₁₂NO₅^- + H⁺ = C₁₃H₁₃NO₅

C₄H₅O^- +  =

By formula: C₄H₅O^- + H⁺ = C₄H₆O

C₃H₂F₅O^- +  =

By formula: C₃H₂F₅O^- + H⁺ = C₃H₃F₅O

C₄H₂F₇O^- +  =

By formula: C₄H₂F₇O^- + H⁺ = C₄H₃F₇O

C₂H₂F^- +  =

By formula: C₂H₂F^- + H⁺ = C₂H₃F

C₃H₂NO^- +  =

By formula: C₃H₂NO^- + H⁺ = C₃H₃NO

C₄H₉O₂^- +  =

By formula: C₄H₉O₂^- + H⁺ = C₄H₁₀O₂

 +  =

By formula: C₅H₄N₅^- + H⁺ = C₅H₅N₅

C₆H₆N₅^- +  =

By formula: C₆H₆N₅^- + H⁺ = C₆H₇N₅

C₃H₃F₂O^- +  =

By formula: C₃H₃F₂O^- + H⁺ = C₃H₄F₂O

 +  =

By formula: C₆H₃^- + H⁺ = C₆H₄

C₄H₄P^- +  = C₄H₅P

By formula: C₄H₄P^- + H⁺ = C₄H₅P

C₄H₄As^- +  = C₄H₅As

By formula: C₄H₄As^- + H⁺ = C₄H₅As

C₁₀H₁₃NO₂^- +  = C₁₀H₁₄NO₂

By formula: C₁₀H₁₃NO₂^- + H⁺ = C₁₀H₁₄NO₂

C₈H₁₀FSi^- +  = C₈H₁₁FSi

By formula: C₈H₁₀FSi^- + H⁺ = C₈H₁₁FSi

C₈H₁₀NO₂Si^- +  = C₈H₁₁NO₂Si

By formula: C₈H₁₀NO₂Si^- + H⁺ = C₈H₁₁NO₂Si

 +  =

By formula: C₈H₇^- + H⁺ = C₈H₈

C₉H₁₀F₃Si^- +  = C₉H₁₁F₃Si

By formula: C₉H₁₀F₃Si^- + H⁺ = C₉H₁₁F₃Si

CH₃O₃S^- +  = CH₄O₃S

By formula: CH₃O₃S^- + H⁺ = CH₄O₃S

C₉H₁₃OSi^- +  = C₉H₁₄OSi

By formula: C₉H₁₃OSi^- + H⁺ = C₉H₁₄OSi

C₈H₁₀FSi^- +  = C₈H₁₁FSi

By formula: C₈H₁₀FSi^- + H⁺ = C₈H₁₁FSi

C₈H₁₀ClSi^- +  = C₈H₁₁ClSi

By formula: C₈H₁₀ClSi^- + H⁺ = C₈H₁₁ClSi

C₈H₁₀ClSi^- +  = C₈H₁₁ClSi

By formula: C₈H₁₀ClSi^- + H⁺ = C₈H₁₁ClSi

C₉H₁₀F₃Si^- +  = C₉H₁₁F₃Si

By formula: C₉H₁₀F₃Si^- + H⁺ = C₉H₁₁F₃Si

C₃HF₄O^- +  =

By formula: C₃HF₄O^- + H⁺ = C₃H₂F₄O

C₅H₅S^- +  =

By formula: C₅H₅S^- + H⁺ = C₅H₆S

C₈H₁₁Si^- +  =

By formula: C₈H₁₁Si^- + H⁺ = C₈H₁₂Si

C₆HCl₄^- +  =

By formula: C₆HCl₄^- + H⁺ = C₆H₂Cl₄

C₂H₂NO₂^- +  =

By formula: C₂H₂NO₂^- + H⁺ = C₂H₃NO₂

C₆HCl₄^- +  =

By formula: C₆HCl₄^- + H⁺ = C₆H₂Cl₄

C₄H₄N^- +  =

By formula: C₄H₄N^- + H⁺ = C₄H₅N

C₃H₄FO^- +  =

By formula: C₃H₄FO^- + H⁺ = C₃H₅FO

C₆H₂Cl₃^- +  =

By formula: C₆H₂Cl₃^- + H⁺ = C₆H₃Cl₃

H₂O₄P^- +  =

By formula: H₂O₄P^- + H⁺ = H₃O₄P

References

Go To: Top, Reaction thermochemistry data, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Adcock, Baran, et al., 2005
Adcock, W.; Baran, Y.; Filippi, A.; Speranza, M.; Trout, N.A., Polar substituent effects in the bicyclo[1.1.1]pentane ring system: Acidities of 3-substituted bicyclo[1.1.1]pentane-1-carboxylic acids, J. Org. Chem., 2005, 70, 3, 1029-1034, https://doi.org/10.1021/jo040236b . [all data]

Janousek, Reed, et al., 1980
Janousek, B.K.; Reed, K.J.; Brauman, J.I., Electron photodetachment from mercaptyl anions (RS- electron affinities of mercaptyl radicals and the S-H bond strength in mercaptans), J. Am. Chem. Soc., 1980, 102, 3125. [all data]

Bartmess, Scott, et al., 1979
Bartmess, J.E.; Scott, J.A.; McIver, R.T., Jr., The gas phase acidity scale from methanol to phenol, J. Am. Chem. Soc., 1979, 101, 6047. [all data]

Bartmess and Burnham, 1984
Bartmess, J.E.; Burnham, R., Effect of central substituents on the gas phase acidities of propenes, J. Org. Chem., 1984, 49, 1382. [all data]

Kleingeld and Nibbering, 1984
Kleingeld, J.C.; Nibbering, N.M.M., Negative Ion/Molecule Cycloaddition Reactions of 2-Methylpropenal in the Gas Phase, Recl. Trav. Chim. Pays-Bas, 1984, 103, 3, 87, https://doi.org/10.1002/recl.19841030303 . [all data]

Neumark, Lykke, et al., 1985
Neumark, D.M.; Lykke, K.R.; Andersen, T.; Lineberger, W.C., Laser photodetachment measurement of the electron affinity of atomic oxygen, Phys. Rev. A:, 1985, 32, 1890. [all data]

Farid and McMahon, 1980
Farid, R.; McMahon, T.B., The gas phase acidities of fluorinated acetones. An ICR investigation of the role of fluorine substituents in the stabilization of planar carbanions, Can. J. Chem., 1980, 58, 2307. [all data]

Meot-ner and Kafafi, 1988
Meot-ner, M.; Kafafi, S.A., Carbon Acidities of Aromatic Compounds, J. Am. Chem. Soc., 1988, 110, 19, 6297, https://doi.org/10.1021/ja00227a003 . [all data]

Kiefer, Zhang, et al., 1997
Kiefer, J.H.; Zhang, Q.; Kern, R.D.; Yao, J.; Jursic, B., Pyrolysis of Aromatic Azines: Pyrazine, Pyrimidine, and Pyridine, J. Phys. Chem. A, 1997, 101, 38, 7061, https://doi.org/10.1021/jp970211z . [all data]

Meot-ner, Liebman, et al., 1988
Meot-ner, M.; Liebman, J.F.; Kafafi, S.A., Ionic Probes of Aromaticity in Annelated Rings, J. Am. Chem. Soc., 1988, 110, 18, 5937, https://doi.org/10.1021/ja00226a001 . [all data]

Attina, Cacace, et al., 1993
Attina, M.; Cacace, F.; Ciliberto, E.; Depetris, G.; Grandinetti, F.; Pepi, F.; Ricci, A., Gas-Phase Ion Chemistry of Nitramide - A Mass Spectrometric and Abinitio Study of H2N-NO2 and the H2N-NO2+., H2N-NO2.H+, and HN-NO2-, J. Am. Chem. Soc., 1993, 115, 26, 12398, https://doi.org/10.1021/ja00079a022 . [all data]

Gurvich, Veyts, et al.
Gurvich, L.V.; Veyts, I.V.; Alcock, C.B., Hemisphere Publishing, NY, 1989, V. 1 2, Thermodynamic Properties of Individual Substances, 4th Ed. [all data]

Hill and Squires, 1998
Hill, B.T.; Squires, R.R., Synthesis and Characterization of the Negative Ion of non-Kekule` Benzene, J. Chem. Soc. Perkin Trans., 1998, 2, 5, 1027, https://doi.org/10.1039/a707470k . [all data]

Ren, Workman, et al., 1998
Ren, J.H.; Workman, D.B.; Squires, R.R., Gas-phase negative ion chemistry of Lewis acid-base complexes, J. Am. Chem. Soc., 1998, 120, 40, 10511-10522, https://doi.org/10.1021/ja9804518 . [all data]

Graul and Squires, 1990
Graul, S.T.; Squires, R.R., Gas-Phase Acidities Derived from Threshold Energies for Activated Reactions, J. Am. Chem. Soc., 1990, 112, 7, 2517, https://doi.org/10.1021/ja00163a007 . [all data]

Maas and van Keelen, 1989
Maas, W.P.M.; van Keelen, P.A., On the Generation and Characterization of the Spiro[2,5]Octadienyl Anion in the Gas Phase, Org. Mass Spectrom., 1989, 24, 8, 546, https://doi.org/10.1002/oms.1210240807 . [all data]

Mishima, Matsuoka, et al., 2004
Mishima, M.; Matsuoka, M.; Lei, Y.X.; Rappoport, Z., Gas-phase acidities of disubstituted methanes and of enols of carboxamides substituted by electron-withdrawing groups, J. Org. Chem., 2004, 69, 18, 5947-5965, https://doi.org/10.1021/jo040196b . [all data]

Baschky, Peterson, et al., 1994
Baschky, M.C.; Peterson, K.C.; Kass, S.R., Stereospecificity in the gas phase. Formation and characterization of configurationally stable cyclopropyl anions, J. Am. Chem. Soc., 1994, 116, 16, 7218, https://doi.org/10.1021/ja00095a026 . [all data]

Dawson and Jennings, 1977
Dawson, J.H.J.; Jennings, K.R., Relative gas phase acidities of some fluoroalcohols, Int. J. Mass Spectrom. Ion Phys., 1977, 25, 47. [all data]

Rabasco and Kass, 1992
Rabasco, J.J.; Kass, S.R., Reactions of Strong Bases with Vinyl Fluoride Formation and Characterization of 1-Fluorovinyl Anion and the Fluoride-Acetylene Hydrogen-Bond, J. Am. Soc. Mass Spectrom., 1992, 3, 2, 91, https://doi.org/10.1016/1044-0305(92)87041-V . [all data]

Taft, 1987
Taft, R.W., The Nature and Analysis of Substitutent Electronic Effects, Personal communication. See also Prog. Phys. Org. Chem., 1987, 16, 1. [all data]

Brauman and Blair, 1968
Brauman, J.I.; Blair, L.K., Gas Phase Acidities of Carbon Acids, J. Am. Chem. Soc., 1968, 90, 20, 5636, https://doi.org/10.1021/ja01022a073 . [all data]

Crowder and Bartmess, 1993
Crowder, C.; Bartmess, J., The Gas Phase Acidities of Diols, J. Am. Soc. Mass Spectrom., 1993, 4, 9, 723, https://doi.org/10.1016/1044-0305(93)80051-Y . [all data]

Houriet, Tabet, et al., 1984
Houriet, R.; Tabet, J.-C.; Tchapla, A., Gas-phase Acidities of Aliphatic and Cyclic Diols, Spectros. Int. J., (1984),, 1984, 3, 132.. [all data]

Sharma and Lee, 2002
Sharma, S.; Lee, J.K., Acidity of adenine and adenine derivatives and biological implications. A computational and experimental gas-phase study, J. Org. Chem., 2002, 67, 24, 8360-8365, https://doi.org/10.1021/jo0204303 . [all data]

Guo and Grabowski, 1991
Guo, Y.L.; Grabowski, J.J., Reactions of the Benzyne Radical Anion in the Gas Phase, the Acidity of the Phenyl Radical, and the Heat of Formation of ortho-Benzyne, J. Am. Chem. Soc., 1991, 113, 16, 5923, https://doi.org/10.1021/ja00016a001 . [all data]

Gronert and DePuy, 1989
Gronert, S.; DePuy, C.H., The Dehydrophenyl Anion and the Gas Phase Ion Chemistry of Benzyne, J. Am. Chem. Soc., 1989, 111, 26, 9253, https://doi.org/10.1021/ja00208a032 . [all data]

Sunderlin, Panu, et al., 1994
Sunderlin, L.S.; Panu, D.; Puranik, D.B.; Ashe, A.J.; Squires, R.R., Gas-phase properties and reactivities of phospholide and arsolide anions, Organomet., 1994, 13, 12, 4732, https://doi.org/10.1021/om00024a019 . [all data]

Strittmatter, Wong, et al., 2000
Strittmatter, E.F.; Wong, R.L.; Williams, E.R., Gas-phase basicity of (CH3)(3)N+-C6H4-COO- zwitterions: A new class of organic super bases, J. Am. Chem. Soc., 2000, 122, 6, 1247-1248, https://doi.org/10.1021/ja9934495 . [all data]

Irie, Kikukawa, et al., 2001
Irie, M.; Kikukawa, K.; Shimizu, N.; Mishima, M., Gas-phase acidities of aryldimethylsilanes, J. Chem. Soc. Perkin Trans., 2001, 2, 6, 923-928, https://doi.org/10.1039/b100488n . [all data]

Grabowski and Lum, 1990
Grabowski, J.J.; Lum, R.C., Selectivity as a Function of Anionic Base Properties in the Gas Phase Reactions of Dimethyl Sulfite, J. Am. Chem. Soc., 1990, 112, 2, 607, https://doi.org/10.1021/ja00158a018 . [all data]

DePuy, Kass, et al., 1988
DePuy, C.H.; Kass, S.R.; Bean, G.P., Formation and Reactions of Heteroaromatic Anions in the Gas Phase, J. Org. Chem., 1988, 53, 19, 4427, https://doi.org/10.1021/jo00254a001 . [all data]

Schlosser, Marzi, et al., 2001
Schlosser, M.; Marzi, E.; Cottet, F.; Buker, H.H.; Nibbering, N.M.M., The acidity of chloro-substituted benzenes: A comparison of gas phase, ab initio, and kinetic data, Chem. Eur. J., 2001, 7, 16, 3511-3516, https://doi.org/10.1002/1521-3765(20010817)7:16<3511::AID-CHEM3511>3.0.CO;2-U . [all data]

Shiga, Yamaoka, et al., 1972
Shiga, T.; Yamaoka, H.; Arakawa, K.; Suguira, T., A negative ion-molecule reaction in nitroethylene, Bull. Chem. Soc. Jpn., 1972, 45, 2065. [all data]

Bartmess, 1980
Bartmess, J.E., Solvent effects on ion-molecule reactions. Vinyl anions vs. conjugate addition, J. Am. Chem. Soc., 1980, 102, 2483. [all data]

Morris, Knighton, et al., 1997
Morris, R.A.; Knighton, W.B.; Viggiano, A.A.; Hoffman, B.C.; Schaeffer III, H.F., The Gas-phase Acidity of H3PO4, J. Chem. Phys., 1997, 106, 9, 3545, https://doi.org/10.1063/1.473465 . [all data]

Notes

Go To: Top, Reaction thermochemistry data, References

• Symbols used in this document:
  

  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
• The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
• Customer support for NIST Standard Reference Data products.