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Hydrogen cation


Reaction thermochemistry data

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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 301 to 350

C6H2Cl3- + Hydrogen cation = Benzene, 1,2,3-trichloro-

By formula: C6H2Cl3- + H+ = C6H3Cl3

Quantity Value Units Method Reference Comment
Deltar374.9 ± 2.1kcal/molG+TSSchlosser, Marzi, et al., 2001gas phase; Acid: 1,2,3-trichlorobenzene. Anion assigned based on ab initio calculations.
Quantity Value Units Method Reference Comment
Deltar366.8 ± 2.0kcal/molIMRESchlosser, Marzi, et al., 2001gas phase; Acid: 1,2,3-trichlorobenzene. Anion assigned based on ab initio calculations.

C6H7- + Hydrogen cation = 1,3-Cyclohexadiene

By formula: C6H7- + H+ = C6H8

Quantity Value Units Method Reference Comment
Deltar373.2 ± 4.1kcal/molG+TSLee and Squires, 1986gas phase; Between SiH4, tBuOH; value altered from reference due to change in acidity scale
Quantity Value Units Method Reference Comment
Deltar365.8 ± 4.0kcal/molIMRBLee and Squires, 1986gas phase; Between SiH4, tBuOH; value altered from reference due to change in acidity scale

C4H- + Hydrogen cation = 1,3-Butadiyne

By formula: C4H- + H+ = C4H2

Quantity Value Units Method Reference Comment
Deltar360.3 ± 3.2kcal/molD-EAPino, Tulej, et al., 2002gas phase
Deltar360.4 ± 2.9kcal/molEndoShi and Ervin, 2000gas phase
Quantity Value Units Method Reference Comment
Deltar352.1 ± 3.3kcal/molH-TSPino, Tulej, et al., 2002gas phase
Deltar352.2 ± 3.0kcal/molH-TSShi and Ervin, 2000gas phase

C5H7- + Hydrogen cation = 1,3-Pentadiene, (E)-

By formula: C5H7- + H+ = C5H8

Quantity Value Units Method Reference Comment
Deltar369.2 ± 1.2kcal/molD-EAZimmerman, Gygax, et al., 1978gas phase; Acid: 1,4-pentadiene. (Z)-1,3-pentadiene is 7.0 kcal/mol more stable(weaker acid)
Quantity Value Units Method Reference Comment
Deltar364.4 ± 1.9kcal/molH-TSZimmerman, Gygax, et al., 1978gas phase; Acid: 1,4-pentadiene. (Z)-1,3-pentadiene is 7.0 kcal/mol more stable(weaker acid)

HS2- + Hydrogen cation = Dihydrogen disulfide

By formula: HS2- + H+ = H2S2

Quantity Value Units Method Reference Comment
Deltar345.8 ± 3.6kcal/molD-EAEntfellner and Boesl, 2009gas phase
Deltar346.0 ± 3.1kcal/molG+TSOhair, Depuy, et al., 1993gas phase
Quantity Value Units Method Reference Comment
Deltar338.8 ± 3.7kcal/molH-TSEntfellner and Boesl, 2009gas phase
Deltar339.0 ± 3.0kcal/molIMRBOhair, Depuy, et al., 1993gas phase

C8H11- + Hydrogen cation = 1,3-Cyclooctadiene

By formula: C8H11- + H+ = C8H12

Quantity Value Units Method Reference Comment
Deltar376.7 ± 3.1kcal/molG+TSLee and Squires, 1986gas phase; Between EtOH, nPrOH; value altered from reference due to change in acidity scale
Quantity Value Units Method Reference Comment
Deltar370.1 ± 3.0kcal/molIMRBLee and Squires, 1986gas phase; Between EtOH, nPrOH; value altered from reference due to change in acidity scale

C2F5- + Hydrogen cation = Ethane, pentafluoro-

By formula: C2F5- + H+ = C2HF5

Quantity Value Units Method Reference Comment
Deltar374.5 ± 3.3kcal/molG+TSSullivan and Beauchamp, 1976gas phase; Between tBuOH and HF; value altered from reference due to change in acidity scale
Quantity Value Units Method Reference Comment
Deltar366.8 ± 3.2kcal/molIMRBSullivan and Beauchamp, 1976gas phase; Between tBuOH and HF; value altered from reference due to change in acidity scale

cyclobutene-1-ide anion + Hydrogen cation = Cyclobutene

By formula: C4H5- + H+ = C4H6

Quantity Value Units Method Reference Comment
Deltar404.6 ± 1.5kcal/molCIDCTian, Fattahi, et al., 2006gas phase
Deltar397.1 ± 5.1kcal/molG+TSKass, Filley, et al., 1986gas phase
Quantity Value Units Method Reference Comment
Deltar396.5 ± 1.6kcal/molH-TSTian, Fattahi, et al., 2006gas phase
Deltar389.0 ± 5.0kcal/molIMRBKass, Filley, et al., 1986gas phase

C4H7O- + Hydrogen cation = Butanal

By formula: C4H7O- + H+ = C4H8O

Quantity Value Units Method Reference Comment
Deltar364.8 ± 2.1kcal/molD-EAAlconcel, Deyerl, et al., 2001gas phase
Deltar364.1 ± 2.3kcal/molD-EAZimmerman, Reed, et al., 1977gas phase
Quantity Value Units Method Reference Comment
Deltar358.2 ± 2.3kcal/molH-TSAlconcel, Deyerl, et al., 2001gas phase
Deltar357.6 ± 2.5kcal/molH-TSZimmerman, Reed, et al., 1977gas phase

C4H5O- + Hydrogen cation = 2-Butenal

By formula: C4H5O- + H+ = C4H6O

Quantity Value Units Method Reference Comment
Deltar354.7 ± 2.1kcal/molG+TSBartmess and Kiplinger, 1986gas phase; Acid: CH3CH=CHCHO; value altered from reference due to change in acidity scale
Quantity Value Units Method Reference Comment
Deltar348.1 ± 2.0kcal/molIMREBartmess and Kiplinger, 1986gas phase; Acid: CH3CH=CHCHO; value altered from reference due to change in acidity scale

BF2O- + Hydrogen cation = Difluorohydroxyborane

By formula: BF2O- + H+ = HBF2O

Quantity Value Units Method Reference Comment
Deltar377.5 ± 8.3kcal/molAcidLarson and McMahon, 1987gas phase; These relative affinities are ca. 10 kcal/mol weaker than threshold values (see Wenthold and Squires, 1995) for donors greater than ca. 27 kcal/mol in free energy. This discrepancy has not yet been resolved, though the stronger value appears preferable.

C3H8B- + Hydrogen cation = Borane, trimethyl-

By formula: C3H8B- + H+ = C3H9B

Quantity Value Units Method Reference Comment
Deltar366.2 ± 6.1kcal/molG+TSMurphy and Beauchamp, 1976gas phase; Between AsH3,PH3; value altered from reference due to change in acidity scale
Quantity Value Units Method Reference Comment
Deltar358.9 ± 6.0kcal/molIMRBMurphy and Beauchamp, 1976gas phase; Between AsH3,PH3; value altered from reference due to change in acidity scale

C9H4N3O2- + Hydrogen cation = C9H5N3O2

By formula: C9H4N3O2- + H+ = C9H5N3O2

Quantity Value Units Method Reference Comment
Deltar308.7 ± 2.3kcal/molG+TSKoppel, Taft, et al., 1994gas phase; Per Leito, Raamat, et al., 2009, dGacid is likely too weak by up to 1.3 kcal/mol.
Quantity Value Units Method Reference Comment
Deltar303.0 ± 2.0kcal/molIMREKoppel, Taft, et al., 1994gas phase; Per Leito, Raamat, et al., 2009, dGacid is likely too weak by up to 1.3 kcal/mol.

C5H9O- + Hydrogen cation = 2-Butanone, 3-methyl-

By formula: C5H9O- + H+ = C5H10O

Quantity Value Units Method Reference Comment
Deltar369.3 ± 2.7kcal/molG+TSChyall, Brickhouse, et al., 1994gas phase; By equilibration, more substituted site is less acidic than Me by 2.3 kcal/mol
Quantity Value Units Method Reference Comment
Deltar362.8 ± 2.5kcal/molIMREChyall, Brickhouse, et al., 1994gas phase; By equilibration, more substituted site is less acidic than Me by 2.3 kcal/mol

C4H10NO- + Hydrogen cation = Diethylhydroxylamine

By formula: C4H10NO- + H+ = C4H11NO

Quantity Value Units Method Reference Comment
Deltar370.6 ± 2.1kcal/molG+TSBartmess, Basso, et al., 1983gas phase; See also Mahoney, Mendenhall, et al., 1973, Bordwell and Liu, 1996 for supporting DH values
Quantity Value Units Method Reference Comment
Deltar364.0 ± 2.0kcal/molIMREBartmess, Basso, et al., 1983gas phase; See also Mahoney, Mendenhall, et al., 1973, Bordwell and Liu, 1996 for supporting DH values

CH3O2Si- + Hydrogen cation = CH4O2Si

By formula: CH3O2Si- + H+ = CH4O2Si

Quantity Value Units Method Reference Comment
Deltar361.4 ± 6.1kcal/molG+TSDamrauer and Krempp, 1990gas phase; Between EtCHO,(Me3Si)2NH. Value revised, based on data in Grimm and Bartmess, 1992.
Quantity Value Units Method Reference Comment
Deltar354.0 ± 6.0kcal/molIMRBDamrauer and Krempp, 1990gas phase; Between EtCHO,(Me3Si)2NH. Value revised, based on data in Grimm and Bartmess, 1992.

C4H4F3O2S- + Hydrogen cation = C4H5F3O2S

By formula: C4H4F3O2S- + H+ = C4H5F3O2S

Quantity Value Units Method Reference Comment
Deltar343.3 ± 2.1kcal/molG+TSTaft, 1987gas phase; Acid = CF3SO2CH2CH=CH2; value altered from reference due to change in acidity scale
Quantity Value Units Method Reference Comment
Deltar336.2 ± 2.0kcal/molIMRETaft, 1987gas phase; Acid = CF3SO2CH2CH=CH2; value altered from reference due to change in acidity scale

C6H3Cl2- + Hydrogen cation = Benzene, 1,3-dichloro-

By formula: C6H3Cl2- + H+ = C6H4Cl2

Quantity Value Units Method Reference Comment
Deltar374.0 ± 2.1kcal/molG+TSSchlosser, Marzi, et al., 2001gas phase; Acid: m-dichlorobenzene. Anion assigned based on ab initio calculations.
Quantity Value Units Method Reference Comment
Deltar366.3 ± 2.0kcal/molIMRESchlosser, Marzi, et al., 2001gas phase; Acid: m-dichlorobenzene. Anion assigned based on ab initio calculations.

C8H9- + Hydrogen cation = Bicyclo[3.2.1]octa-2,6-diene

By formula: C8H9- + H+ = C8H10

Quantity Value Units Method Reference Comment
Deltar379.5 ± 2.1kcal/molG+TSLee and Squires, 1986gas phase; 1.4 kcal > MeOH; value altered from reference due to change in acidity scale
Quantity Value Units Method Reference Comment
Deltar372.6 ± 2.0kcal/molIMRELee and Squires, 1986gas phase; 1.4 kcal > MeOH; value altered from reference due to change in acidity scale

CH5Ge- + Hydrogen cation = CH6Ge

By formula: CH5Ge- + H+ = CH6Ge

Quantity Value Units Method Reference Comment
Deltar367.3 ± 2.1kcal/molG+TSDecouzon, Gal, et al., 1993gas phase
Deltar366.7 ± 2.1kcal/molG+TSGal, Decouzon, et al., 2001gas phase
Quantity Value Units Method Reference Comment
Deltar359.3 ± 2.0kcal/molIMREDecouzon, Gal, et al., 1993gas phase
Deltar358.7 ± 2.0kcal/molIMREGal, Decouzon, et al., 2001gas phase

C6H3Cl2- + Hydrogen cation = Benzene, 1,2-dichloro-

By formula: C6H3Cl2- + H+ = C6H4Cl2

Quantity Value Units Method Reference Comment
Deltar377.1 ± 2.1kcal/molG+TSSchlosser, Marzi, et al., 2001gas phase; Acid: o-dichlorobenzene. Anion assigned based on ab initio calculations.
Quantity Value Units Method Reference Comment
Deltar368.7 ± 2.0kcal/molIMRESchlosser, Marzi, et al., 2001gas phase; Acid: o-dichlorobenzene. Anion assigned based on ab initio calculations.

C9H11- + Hydrogen cation = 1,3,5-Cycloheptatriene, 7-ethyl-

By formula: C9H11- + H+ = C9H12

Quantity Value Units Method Reference Comment
Deltar370.2 ± 2.5kcal/molG+TSMishima, Kinoshita, et al., 2002gas phase; Reprotonation likely to be on C-1, giving 1-alkyl-cycloheptatriene - JEB
Quantity Value Units Method Reference Comment
Deltar362.5 ± 2.0kcal/molIMREMishima, Kinoshita, et al., 2002gas phase; Reprotonation likely to be on C-1, giving 1-alkyl-cycloheptatriene - JEB

C10H13- + Hydrogen cation = C10H14

By formula: C10H13- + H+ = C10H14

Quantity Value Units Method Reference Comment
Deltar369.5 ± 2.5kcal/molG+TSMishima, Kinoshita, et al., 2002gas phase; Reprotonation likely to be on C-1, giving 1-alkyl-cycloheptatriene - JEB
Quantity Value Units Method Reference Comment
Deltar361.7 ± 2.0kcal/molIMREMishima, Kinoshita, et al., 2002gas phase; Reprotonation likely to be on C-1, giving 1-alkyl-cycloheptatriene - JEB

C10H13- + Hydrogen cation = C10H14

By formula: C10H13- + H+ = C10H14

Quantity Value Units Method Reference Comment
Deltar369.1 ± 2.5kcal/molG+TSMishima, Kinoshita, et al., 2002gas phase; Reprotonation likely to be on C-1, giving 1-alkyl-cycloheptatriene - JEB
Quantity Value Units Method Reference Comment
Deltar361.4 ± 2.0kcal/molIMREMishima, Kinoshita, et al., 2002gas phase; Reprotonation likely to be on C-1, giving 1-alkyl-cycloheptatriene - JEB

C11H15- + Hydrogen cation = C11H16

By formula: C11H15- + H+ = C11H16

Quantity Value Units Method Reference Comment
Deltar368.7 ± 2.5kcal/molG+TSMishima, Kinoshita, et al., 2002gas phase; Reprotonation likely to be on C-1, giving 1-alkyl-cycloheptatriene - JEB
Quantity Value Units Method Reference Comment
Deltar361.0 ± 2.0kcal/molIMREMishima, Kinoshita, et al., 2002gas phase; Reprotonation likely to be on C-1, giving 1-alkyl-cycloheptatriene - JEB

V- + Hydrogen cation = HV

By formula: V- + H+ = HV

Quantity Value Units Method Reference Comment
Deltar339.7 ± 3.4kcal/molG+TSSallans, Lane, et al., 1985gas phase
Deltar340.9 ± 3.7kcal/molAcidFeigerle, Corderman, et al., 1981gas phase
Quantity Value Units Method Reference Comment
Deltar332.0 ± 3.0kcal/molIMRBSallans, Lane, et al., 1985gas phase
Deltar333.1 ± 5.2kcal/molH-TSFeigerle, Corderman, et al., 1981gas phase

C8H9- + Hydrogen cation = 7-Methylcycloheptatriene

By formula: C8H9- + H+ = C8H10

Quantity Value Units Method Reference Comment
Deltar371.0 ± 2.5kcal/molG+TSMishima, Kinoshita, et al., 2002gas phase; Reprotonation likely to be on C-1, giving 1-alkyl-cycloheptatriene - JEB
Quantity Value Units Method Reference Comment
Deltar363.3 ± 2.0kcal/molIMREMishima, Kinoshita, et al., 2002gas phase; Reprotonation likely to be on C-1, giving 1-alkyl-cycloheptatriene - JEB

C2H6BO3- + Hydrogen cation = C2H7BO3

By formula: C2H6BO3- + H+ = C2H7BO3

Quantity Value Units Method Reference Comment
Deltar360.2 ± 4.6kcal/molG+TSKiplinger, Crowder, et al., 1994gas phase; between tBuCH=NOH, pyrrole. Stein, Rikkers, et al. is wrong on GpAd for (MeO)2BOH
Quantity Value Units Method Reference Comment
Deltar353.4 ± 4.5kcal/molIMRBKiplinger, Crowder, et al., 1994gas phase; between tBuCH=NOH, pyrrole. Stein, Rikkers, et al. is wrong on GpAd for (MeO)2BOH

C3H5- + Hydrogen cation = Propene

By formula: C3H5- + H+ = C3H6

Quantity Value Units Method Reference Comment
Deltar405.8 ± 2.0kcal/molBranDePuy, Gronert, et al., 1989gas phase
Deltar>404.75 ± 0.60kcal/molG+TSFroelicher, Freiser, et al., 1986gas phase
Quantity Value Units Method Reference Comment
Deltar398.0 ± 2.1kcal/molH-TSDePuy, Gronert, et al., 1989gas phase
Deltar>397.00kcal/molIMRBFroelicher, Freiser, et al., 1986gas phase

C4H6NO4S- + Hydrogen cation = C4H7NO4S

By formula: C4H6NO4S- + H+ = C4H7NO4S

Quantity Value Units Method Reference Comment
Deltar330.0 ± 2.1kcal/molG+TSBouchoux, Jaudon, et al., 1991gas phase; AM1 implies oximate anion (authors), may be carbanion by struct/react.-JEB
Quantity Value Units Method Reference Comment
Deltar323.4 ± 2.0kcal/molIMREBouchoux, Jaudon, et al., 1991gas phase; AM1 implies oximate anion (authors), may be carbanion by struct/react.-JEB

H2NOSi- + Hydrogen cation = H3NOSi

By formula: H2NOSi- + H+ = H3NOSi

Quantity Value Units Method Reference Comment
Deltar359.5 ± 4.2kcal/molG+TSHankin, Krempp, et al., 1995gas phase; Between CF3CH2OH,MeSH, but poor thresholds due to competeting reactions.
Quantity Value Units Method Reference Comment
Deltar352.3 ± 4.0kcal/molIMRBHankin, Krempp, et al., 1995gas phase; Between CF3CH2OH,MeSH, but poor thresholds due to competeting reactions.

C7H19Si2- + Hydrogen cation = Silane, methylenebis[trimethyl-

By formula: C7H19Si2- + H+ = C7H20Si2

Quantity Value Units Method Reference Comment
Deltar373.6 ± 2.2kcal/molG+TSRomer, Gatev, et al., 1998gas phase
Deltar373.6 ± 4.0kcal/molD-EABrinkman, Berger, et al., 1994gas phase
Quantity Value Units Method Reference Comment
Deltar365.9 ± 2.0kcal/molIMRERomer, Gatev, et al., 1998gas phase
Deltar365.8 ± 4.1kcal/molH-TSBrinkman, Berger, et al., 1994gas phase

C4H7O2- + Hydrogen cation = Ethyl Acetate

By formula: C4H7O2- + H+ = C4H8O2

Quantity Value Units Method Reference Comment
Deltar371.7 ± 4.1kcal/molG+TSHaas, Giblin, et al., 1998gas phase; From transesterification equilibria
Deltar368.9 ± 1.2kcal/molEIAEMuftakhov, Vasil'ev, et al., 1999gas phase
Quantity Value Units Method Reference Comment
Deltar365.0 ± 4.0kcal/molIMREHaas, Giblin, et al., 1998gas phase; From transesterification equilibria

C3H6NO2- + Hydrogen cation = Alanine

By formula: C3H6NO2- + H+ = C3H7NO2

Quantity Value Units Method Reference Comment
Deltar341.8 ± 1.9kcal/molCIDCJones, Bernier, et al., 2007gas phase
Deltar340.7 ± 2.1kcal/molG+TSLocke and McIver, 1983gas phase
Quantity Value Units Method Reference Comment
Deltar334.8 ± 2.0kcal/molH-TSJones, Bernier, et al., 2007gas phase
Deltar333.7 ± 2.0kcal/molIMRELocke and McIver, 1983gas phase

CH4N- + Hydrogen cation = Methylamine

By formula: CH4N- + H+ = CH5N

Quantity Value Units Method Reference Comment
Deltar402.0 ± 2.6kcal/molD-EARadisic, Xu, et al., 2002gas phase
Deltar403.21 ± 0.82kcal/molG+TSMacKay, Hemsworth, et al., 1976gas phase
Quantity Value Units Method Reference Comment
Deltar394.5 ± 2.7kcal/molH-TSRadisic, Xu, et al., 2002gas phase
Deltar395.70 ± 0.70kcal/molIMREMacKay, Hemsworth, et al., 1976gas phase

C4F9O- + Hydrogen cation = 1,1,1,3,3,3-Hexafluoro-2-(trifluoromethyl)-2-propanol

By formula: C4F9O- + H+ = C4HF9O

Quantity Value Units Method Reference Comment
Deltar331.6 ± 2.2kcal/molG+TSTaft, Koppel, et al., 1990gas phase
Quantity Value Units Method Reference Comment
Deltar324.0 ± 2.0kcal/molIMRETaft, Koppel, et al., 1990gas phase
Deltar323.2 ± 5.0kcal/molIMRBKoppel, Pikver, et al., 1981gas phase
Deltar321.4 ± 5.0kcal/molIMRBClair and McMahon, 1980gas phase

C9H5N2- + Hydrogen cation = Malononitrile, phenyl-

By formula: C9H5N2- + H+ = C9H6N2

Quantity Value Units Method Reference Comment
Deltar320.3 ± 2.1kcal/molG+TSKoppel, Taft, et al., 1994gas phase
Deltar320.7 ± 2.1kcal/molG+TSTaft and Bordwell, 1988gas phase
Quantity Value Units Method Reference Comment
Deltar314.3 ± 2.0kcal/molIMREKoppel, Taft, et al., 1994gas phase
Deltar314.7 ± 2.0kcal/molIMRETaft and Bordwell, 1988gas phase

C2HO- + Hydrogen cation = Ketene

By formula: C2HO- + H+ = C2H2O

Quantity Value Units Method Reference Comment
Deltar364.8 ± 2.1kcal/molG+TSOakes, Jones, et al., 1983gas phase; Acid: ketene; value altered from reference due to change in acidity scale
Quantity Value Units Method Reference Comment
Deltar357.8 ± 2.0kcal/molIMRBOakes, Jones, et al., 1983gas phase; Acid: ketene; value altered from reference due to change in acidity scale

C5H9O2- + Hydrogen cation = Pentanoic acid

By formula: C5H9O2- + H+ = C5H10O2

Quantity Value Units Method Reference Comment
Deltar346.2 ± 2.1kcal/molG+TSCaldwell, Renneboog, et al., 1989gas phase
Deltar346.1 ± 2.4kcal/molG+TSMcLuckey, Cameron, et al., 1981gas phase
Quantity Value Units Method Reference Comment
Deltar339.2 ± 2.0kcal/molIMRECaldwell, Renneboog, et al., 1989gas phase
Deltar339.1 ± 2.3kcal/molCIDCMcLuckey, Cameron, et al., 1981gas phase

C4H7- + Hydrogen cation = Cyclobutane

By formula: C4H7- + H+ = C4H8

Quantity Value Units Method Reference Comment
Deltar417.4 ± 2.0kcal/molBranDePuy, Gronert, et al., 1989gas phase
Deltar419.9 ± 2.0kcal/molBranPeerboom, Rademaker, et al., 1992gas phase
Quantity Value Units Method Reference Comment
Deltar408.4 ± 2.1kcal/molH-TSDePuy, Gronert, et al., 1989gas phase
Deltar410.9 ± 2.1kcal/molH-TSPeerboom, Rademaker, et al., 1992gas phase

C5H9- + Hydrogen cation = Cyclopentane

By formula: C5H9- + H+ = C5H10

Quantity Value Units Method Reference Comment
Deltar416.1 ± 2.0kcal/molBranDePuy, Gronert, et al., 1989gas phase
Deltar418.3 ± 2.0kcal/molBranPeerboom, Rademaker, et al., 1992gas phase
Quantity Value Units Method Reference Comment
Deltar407.4 ± 2.1kcal/molH-TSDePuy, Gronert, et al., 1989gas phase
Deltar409.6 ± 2.1kcal/molH-TSPeerboom, Rademaker, et al., 1992gas phase

C4H7- + Hydrogen cation = 1-Butene

By formula: C4H7- + H+ = C4H8

Quantity Value Units Method Reference Comment
Deltar412.0 ± 2.0kcal/molBranDePuy, Gronert, et al., 1989gas phase
Deltar413.2 ± 4.8kcal/molBranPeerboom, Rademaker, et al., 1992gas phase
Quantity Value Units Method Reference Comment
Deltar404.0 ± 2.1kcal/molH-TSDePuy, Gronert, et al., 1989gas phase
Deltar405.2 ± 4.9kcal/molH-TSPeerboom, Rademaker, et al., 1992gas phase

C6H11O2- + Hydrogen cation = Hexanoic acid

By formula: C6H11O2- + H+ = C6H12O2

Quantity Value Units Method Reference Comment
Deltar346.1 ± 2.1kcal/molG+TSCaldwell, Renneboog, et al., 1989gas phase
Deltar345.8 ± 2.4kcal/molG+TSMcLuckey, Cameron, et al., 1981gas phase
Quantity Value Units Method Reference Comment
Deltar339.1 ± 2.0kcal/molIMRECaldwell, Renneboog, et al., 1989gas phase
Deltar338.8 ± 2.3kcal/molCIDCMcLuckey, Cameron, et al., 1981gas phase

C2H5S- + Hydrogen cation = Dimethyl sulfide

By formula: C2H5S- + H+ = C2H6S

Quantity Value Units Method Reference Comment
Deltar390.2 ± 1.5kcal/molD-EAMoran and Ellison, 1988gas phase
Deltar393.2 ± 2.1kcal/molG+TSIngemann and Nibbering, 1985gas phase
Quantity Value Units Method Reference Comment
Deltar383.0 ± 1.7kcal/molH-TSMoran and Ellison, 1988gas phase
Deltar386.0 ± 2.0kcal/molIMREIngemann and Nibbering, 1985gas phase

C4H9- + Hydrogen cation = Isobutane

By formula: C4H9- + H+ = C4H10

Quantity Value Units Method Reference Comment
Deltar412.9 ± 2.0kcal/molBranDePuy, Gronert, et al., 1989gas phase
Deltar414.7 ± 4.8kcal/molBranPeerboom, Rademaker, et al., 1992gas phase
Quantity Value Units Method Reference Comment
Deltar404.3 ± 2.1kcal/molH-TSDePuy, Gronert, et al., 1989gas phase
Deltar406.1 ± 4.9kcal/molH-TSPeerboom, Rademaker, et al., 1992gas phase

C4H7N2O3- + Hydrogen cation = L-Asparagine

By formula: C4H7N2O3- + H+ = C4H8N2O3

Quantity Value Units Method Reference Comment
Deltar331.0 ± 2.2kcal/molCIDCJones, Bernier, et al., 2007gas phase
Deltar331.6 ± 3.1kcal/molG+TSO'Hair, Bowie, et al., 1992gas phase
Quantity Value Units Method Reference Comment
Deltar324.2 ± 2.3kcal/molH-TSJones, Bernier, et al., 2007gas phase
Deltar324.8 ± 3.0kcal/molCIDCO'Hair, Bowie, et al., 1992gas phase

C6H13N4O2- + Hydrogen cation = Arginine

By formula: C6H13N4O2- + H+ = C6H14N4O2

Quantity Value Units Method Reference Comment
Deltar330.1 ± 2.2kcal/molCIDCJones, Bernier, et al., 2007gas phase
Deltar331.7 ± 3.1kcal/molG+TSO'Hair, Bowie, et al., 1992gas phase
Quantity Value Units Method Reference Comment
Deltar323.2 ± 2.3kcal/molH-TSJones, Bernier, et al., 2007gas phase
Deltar324.9 ± 3.0kcal/molCIDCO'Hair, Bowie, et al., 1992gas phase

C6H11- + Hydrogen cation = Cyclohexane

By formula: C6H11- + H+ = C6H12

Quantity Value Units Method Reference Comment
Deltar418.3 ± 2.0kcal/molBranPeerboom, Rademaker, et al., 1992gas phase
Deltar406.82 ± 0.90kcal/molG+TSBohme, Lee-Ruff, et al., 1972gas phase
Quantity Value Units Method Reference Comment
Deltar409.5 ± 2.2kcal/molH-TSPeerboom, Rademaker, et al., 1992gas phase
Deltar>398.00kcal/molIMRBBohme, Lee-Ruff, et al., 1972gas phase

MeOCH2CO2 anion + Hydrogen cation = Acetic acid, methoxy-

By formula: C3H5O3- + H+ = C3H6O3

Quantity Value Units Method Reference Comment
Deltar341.9 ± 2.1kcal/molG+TSCaldwell, Renneboog, et al., 1989gas phase
Deltar342.6 ± 2.1kcal/molG+TSTaft and Topsom, 1987gas phase
Quantity Value Units Method Reference Comment
Deltar335.3 ± 2.0kcal/molIMRECaldwell, Renneboog, et al., 1989gas phase
Deltar336.0 ± 2.0kcal/molIMRETaft and Topsom, 1987gas phase

C5H9O- + Hydrogen cation = 2-Butanone, 3-methyl-

By formula: C5H9O- + H+ = C5H10O

Quantity Value Units Method Reference Comment
Deltar367.3 ± 2.2kcal/molG+TSCumming and Kebarle, 1978gas phase; Structure assignment revised to less-substituted site: Chyall, Brickhouse, et al., 1994
Quantity Value Units Method Reference Comment
Deltar360.5 ± 2.0kcal/molIMRECumming and Kebarle, 1978gas phase; Structure assignment revised to less-substituted site: Chyall, Brickhouse, et al., 1994

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.

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]

Lee and Squires, 1986
Lee, R.E.; Squires, R.R., Anionic homoaromaticity: A gas phase experimental study, J. Am. Chem. Soc., 1986, 105, 5078. [all data]

Pino, Tulej, et al., 2002
Pino, T.; Tulej, M.; Guthe, F.; Pachkov, M.; Maier, J.P., Photodetachment spectroscopy of the C2nH- (n=2-4) anions in the vicinity of their electron detachment threshold, J. Chem. Phys., 2002, 116, 14, 6126-6131, https://doi.org/10.1063/1.1451248 . [all data]

Shi and Ervin, 2000
Shi, Y.; Ervin, K.M., Gas-phase acidity and C-H bond energy of diacetylene, Chem. Phys. Lett., 2000, 318, 1-3, 149-154, https://doi.org/10.1016/S0009-2614(00)00023-3 . [all data]

Zimmerman, Gygax, et al., 1978
Zimmerman, A.H.; Gygax, R.; Brauman, J.I., Electron photodetachment spectroscopy of polyene anions. Electron affinities of pentadienyl and heptatrienyl radicals, J. Am. Chem. Soc., 1978, 100, 5595. [all data]

Entfellner and Boesl, 2009
Entfellner, M.; Boesl, U., Photodetachment-photoelectron spectroscopy of disulfanide: the ground and first excited electronic state of HS2 and DS2, Phys. Chem. Chem. Phys., 2009, 11, 15, 2657-2662, https://doi.org/10.1039/b820174a . [all data]

Ohair, Depuy, et al., 1993
Ohair, R.A.J.; Depuy, C.H.; Bierbaum, V.M., Gas-Phase Chemistry and Thermochemistry of the Hydroxysulfide Anion, HOS-, J. Phys. Chem., 1993, 97, 30, 7955, https://doi.org/10.1021/j100132a026 . [all data]

Sullivan and Beauchamp, 1976
Sullivan, S.A.; Beauchamp, J.L., Competition between proton transfer and elimination in the reactions of strong bases with fluoroethanes in the gas phase. Influence of base strength on reactivity, J. Am. Chem. Soc., 1976, 98, 1160. [all data]

Tian, Fattahi, et al., 2006
Tian, Z.X.; Fattahi, A.; Lis, L.; Kass, S.R., Cycloalkane and cycloalkene C-H bond dissociation energies, J. Am. Chem. Soc., 2006, 128, 51, 17087-17092, https://doi.org/10.1021/ja065348u . [all data]

Kass, Filley, et al., 1986
Kass, S.R.; Filley, J.; Van Doren, J.M.; DePuy, C.H., Nitrous oxide in gas-phase ion-molecule chemistry: A versatile reagent for the determination of carbanion structure, J. Am. Chem. Soc., 1986, 108, 2849. [all data]

Alconcel, Deyerl, et al., 2001
Alconcel, L.S.; Deyerl, H.J.; Continetti, R.E., Effects of alkyl substitution on the energetics of enolate anions and radicals, J. Am. Chem. Soc., 2001, 123, 50, 12675-12681, https://doi.org/10.1021/ja0120431 . [all data]

Zimmerman, Reed, et al., 1977
Zimmerman, A.H.; Reed, K.J.; Brauman, J.I., Photodetachment of electrons from enolate anions. Gas phase electron affinities of enolate radicals, J. Am. Chem. Soc., 1977, 99, 7203. [all data]

Bartmess and Kiplinger, 1986
Bartmess, J.E.; Kiplinger, J.P., 'Kinetic' vs. thermodynamic acidities of enones in the gas phase, J. Org. Chem., 1986, 51, 2173. [all data]

Larson and McMahon, 1987
Larson, J.W.; McMahon, T.B., Trends in Gas Phase Fluoride Ion Affinities of the Main Group Oxyfluorides and Fluoride Sulfides. Fluoride Adducts of FAsO, FPO, FPO2, F2SiO, F4SO, FBO, F2SiS, FPS, FAsS, F2S2, and S2O., Inorg. Chem., 1987, 26, 24, 4018, https://doi.org/10.1021/ic00271a011 . [all data]

Wenthold and Squires, 1995
Wenthold, P.G.; Squires, R.R., Bond dissociation energies of F2(-) and HF2(-). A gas-phase experimental and G2 theoretical study, J. Phys. Chem., 1995, 99, 7, 2002, https://doi.org/10.1021/j100007a034 . [all data]

Murphy and Beauchamp, 1976
Murphy, M.K.; Beauchamp, J.L., Acid-base properties and gas-phase ion chemistry of (CH3)3B, J. Am. Chem. Soc., 1976, 98, 1433. [all data]

Koppel, Taft, et al., 1994
Koppel, I.A.; Taft, R.W.; Anvia, F.; Zhu, S.Z.; Hu, L.Q.; Sung, K.S.; Desmarteau, D.D.; Yagupolskii, L.M., The Gas-Phase Acidities of Very Strong Neutral Bronsted Acids, J. Am. Chem. Soc., 1994, 116, 7, 3047, https://doi.org/10.1021/ja00086a038 . [all data]

Leito, Raamat, et al., 2009
Leito, I.; Raamat, E.; Kutt, A.; Saame, J.; Kipper, K.; Koppel, I.A.; Koppel, I.; Zhang, M.; Mishima, M.; Yagupolskii, L.M.; Garlyauskayte, R.Y.; Filatov, A.A., Revision of the Gas-Phase Acidity Scale below 300 kcal mol(-1), J. Phys. Chem. A, 2009, 113, 29, 8421-8424, https://doi.org/10.1021/jp903780k . [all data]

Chyall, Brickhouse, et al., 1994
Chyall, L.J.; Brickhouse, M.D.; Schnute, M.E.; Squires, R.R., Kinetic versus thermodynamic control in the deprotonation of unsymmetrical ketones in the gas phase, J. Am. Chem. Soc., 1994, 116, 19, 8681, https://doi.org/10.1021/ja00098a031 . [all data]

Bartmess, Basso, et al., 1983
Bartmess, J.E.; Basso, T.; eorgiadis, R.M., The electron affinity of a nitroxide radical, J. Phys. Chem., 1983, 87, 912. [all data]

Mahoney, Mendenhall, et al., 1973
Mahoney, L.R.; Mendenhall, G.D.; Ingold, K.U., Calorimetric and Equilibrium Studies on Some Stable Nitroxide and Iminoxy Radicals. Approximate O-H BDEs in Hydroxylamines and Oximes., J. Am. Chem. Soc., 1973, 95, 26, 8610, https://doi.org/10.1021/ja00807a018 . [all data]

Bordwell and Liu, 1996
Bordwell, F.G.; Liu, W.-Z., Solvent Effects on Homolytic Bond Dissociation Energies of Hydroxylic Acids, J. Am. Chem. Soc., 1996, 118, 44, 10819-10823, https://doi.org/10.1021/ja961469q . [all data]

Damrauer and Krempp, 1990
Damrauer, R.; Krempp, M., Gas Phase Ion-Molecule Chemistry of Methoxy-Substituted Silanes: Collision Induced Decomposition of Siloxide Ions Leading to Anions of Silaacetaldehyde and Methyl Silaformate, Organomet., 1990, 9, 4, 999, https://doi.org/10.1021/om00118a015 . [all data]

Grimm and Bartmess, 1992
Grimm, D.T.; Bartmess, J.E., The Intrinsic (Gas Phase) Basicity of some Anions Commonly Used in Condensed-Phase Synthesis, J. Am. Chem. Soc., 1992, 114, 4, 1227, https://doi.org/10.1021/ja00030a016 . [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]

Decouzon, Gal, et al., 1993
Decouzon, M.; Gal, J.F.; Gayraud, J.; Maria, P.C.; Vaglio, G.A.; Volpe, P., Fourier Transform-Ion Cyclotron Resonance Study of the Gas-Phase Acidities of Germane and Methylgermane - Bond Dissociation Energy of German, J. Am. Soc. Mass Spectrom., 1993, 4, 1, 54, https://doi.org/10.1016/1044-0305(93)85042-V . [all data]

Gal, Decouzon, et al., 2001
Gal, J.F.; Decouzon, M.; Maria, P.C.; Gonzalez, A.I.; Mo, O.; Yanez, M.; El Chaouch, S.; Guillemin, J.C., Acidity trends in alpha,beta-unsaturated alkanes, silanes, germanes, and stannanes, J. Am. Chem. Soc., 2001, 123, 26, 6353-6359, https://doi.org/10.1021/ja004079j . [all data]

Mishima, Kinoshita, et al., 2002
Mishima, M.; Kinoshita, T.; Hattori, Y.; Takeuchi, K., Gas-phase acidities of cycloheptatrienes: effects of alkyl groups on the stability of carbanions, Eur. J. Mass Spectrom., 2002, 8, 1, 359-366, https://doi.org/10.1255/ejms.499 . [all data]

Sallans, Lane, et al., 1985
Sallans, L.; Lane, K.R.; Squires, R.R.; Freiser, B.S., Generation and reactions of atomic metal anions in the gas phase. Determination of the heterolytic and homolytic bond energies of VH, VrH, FeH, CoH, and MoH, J. Am. Chem. Soc., 1985, 107, 4379. [all data]

Feigerle, Corderman, et al., 1981
Feigerle, C.S.; Corderman, R.R.; Bobashev, S.V.; Lineberger, W.C., Binding Energies and Structure of Transition Metal Negative Ions, J. Chem. Phys., 1981, 74, 3, 1580, https://doi.org/10.1063/1.441289 . [all data]

Kiplinger, Crowder, et al., 1994
Kiplinger, J.P.; Crowder, C.A.; Sorensen, D.N.; Bartmess, J.E., Gas-Phase Ion-Molecule Chemistry of Borate and Boronate Esters, J. Am. Soc. Mass Spectrom., 1994, 5, 3, 169, https://doi.org/10.1016/1044-0305(94)85030-5 . [all data]

Stein, Rikkers, et al.
Stein, S.E.; Rikkers, J.M.; Brown, R.L., NIST Structure anmd Properties Database and Estimation Program, Ver. 1.1, NIST Standard Reference Database 25. [all data]

DePuy, Gronert, et al., 1989
DePuy, C.H.; Gronert, S.; Barlow, S.E.; Bierbaum, V.M.; Damrauer, R., The Gas Phase Acidities of the Alkanes, J. Am. Chem. Soc., 1989, 111, 6, 1968, https://doi.org/10.1021/ja00188a003 . [all data]

Froelicher, Freiser, et al., 1986
Froelicher, S.W.; Freiser, B.S.; Squires, R.R., The C3H5- isomers. Experimental and theoretical studies of the tautomeric propenyl ions and the cyclopropyl anion in the gas phase, J. Am. Chem. Soc., 1986, 108, 2853. [all data]

Bouchoux, Jaudon, et al., 1991
Bouchoux, G.; Jaudon, P.; Decouzon, M.; Gal, J.-F.; Maria, P.-C., Gas-Phase Acidity of Some alpha-keto Aldoximes: Experiment and Theory, J. Phys. Org. Chem., 1991, 4, 5, 285, https://doi.org/10.1002/poc.610040505 . [all data]

Hankin, Krempp, et al., 1995
Hankin, J.A.; Krempp, M.; Damrauer, R., Gas-phase Chemistry of the Silaformamide Ion, Organomet., 1995, 14, 6, 2652, https://doi.org/10.1021/om00006a011 . [all data]

Romer, Gatev, et al., 1998
Romer, B.; Gatev, G.G.; Zhong, M.; Brauman, J.I., Alpha-Stabilization by Silyl and Phosphino Substitution, J. Am. Chem. Soc., 1998, 120, 12, 2919, https://doi.org/10.1021/ja970279s . [all data]

Brinkman, Berger, et al., 1994
Brinkman, E.A.; Berger, S.; Brauman, J.I., alpha-Silyl-substituent stabilization of carbanions and silyl anions, J. Am. Chem. Soc., 1994, 116, 18, 8304, https://doi.org/10.1021/ja00097a042 . [all data]

Haas, Giblin, et al., 1998
Haas, G.W.; Giblin, D.E.; Gross, M.L., The Mechanism and Thermodynamics of Transesterification of Acetate-Ester Enolates in the Gas Phase, Int. J. Mass Spectrom. Ion Proc., 1998, 172, 1-2, 25, https://doi.org/10.1016/S0168-1176(97)83245-4 . [all data]

Muftakhov, Vasil'ev, et al., 1999
Muftakhov, M.V.; Vasil'ev, Y.V.; Mazunov, V.A., Determination of electron affinity of carbonyl radicals by means of negative ion mass spectrometry, Rapid Commun. Mass Spectrom., 1999, 13, 12, 1104-1108, https://doi.org/10.1002/(SICI)1097-0231(19990630)13:12<1104::AID-RCM619>3.0.CO;2-C . [all data]

Jones, Bernier, et al., 2007
Jones, C.M.; Bernier, M.; Carson, E.; Colyer, K.E.; Metz, R.; Pawlow, A.; Wischow, E.D.; Webb, I.; Andriole, E.J.; Poutsma, J.C., Gas-phase Acities of the 20 Protein Amino Acids, Int. J. Mass Spectrom., 2007, 267, 1-3, 54-62, https://doi.org/10.1016/j.ijms.2007.02.018 . [all data]

Locke and McIver, 1983
Locke, M.J.; McIver, R.T., Jr., Effect of Solvation on the Acid/Base Properties of Glycine, J. Am. Chem. Soc., 1983, 105, 4226. [all data]

Radisic, Xu, et al., 2002
Radisic, D.; Xu, S.J.; Bowen, K.H., Photoelectron spectroscopy of the anions, CH3NH- and (CH3)(2)N- and the anion complexes, H-(CH3NH2) and (CH3)(2)N-[(CH3)(2)NH), Chem. Phys. Lett., 2002, 354, 1-2, 9-13, https://doi.org/10.1016/S0009-2614(01)01470-1 . [all data]

MacKay, Hemsworth, et al., 1976
MacKay, G.J.; Hemsworth, R.S.; Bohme, D.K., Absolute gas-phase acidities of CH3NH2, C2H5NH2, (CH3)2NH, and (CH3)3N, Can. J. Chem., 1976, 54, 1624. [all data]

Taft, Koppel, et al., 1990
Taft, R.W.; Koppel, I.J.; Topsom, R.D.; Anvia, F., Acidities of OH Compounds, including Alcohols, Phenols, Carboxylic Acids, and Mineral Acids, J. Am. Chem. Soc., 1990, 112, 6, 2047, https://doi.org/10.1021/ja00162a001 . [all data]

Koppel, Pikver, et al., 1981
Koppel, I.; Pikver, R.; Sugis, A.; Suurmaa, E.; Lippmaa, E., FTICR Study of Structure and Solvent Effects on Basicity of Some Anions in the Gas Phase, Org. Reac., 1981, 18, 3. [all data]

Clair and McMahon, 1980
Clair, R.L.; McMahon, T.B., An ion cyclotron resonance study of base-induced elimination reactions of fluorinated alcohols and unimolecular loss of HF from chemically activated fluoroalkoxide ions, Int. J. Mass Spectrom. Ion Phys., 1980, 33, 21. [all data]

Taft and Bordwell, 1988
Taft, R.W.; Bordwell, F.G., Structural and Solvent Effects Evaluated from Acidities Measured in Dimethyl Sulfoxide and in the Gas Phase, Acc. Chem. Res., 1988, 21, 12, 463, https://doi.org/10.1021/ar00156a005 . [all data]

Oakes, Jones, et al., 1983
Oakes, J.M.; Jones, M.E.; Bierbaum, V.M.; Ellison, G.B., Photoelectron spectroscopy of CCO- and HCCO-, J. Phys. Chem., 1983, 87, 4810. [all data]

Caldwell, Renneboog, et al., 1989
Caldwell, G.; Renneboog, R.; Kebarle, P., Gas Phase Acidities of Aliphatic Carboxylic Acids, Based on Measurements of Proton Transfer Equilibria, Can. J. Chem., 1989, 67, 4, 661, https://doi.org/10.1139/v89-092 . [all data]

McLuckey, Cameron, et al., 1981
McLuckey, S.A.; Cameron, D.; Cooks, R.G., Proton affinities from the dissociation of proton bound dimers, J. Am. Chem. Soc., 1981, 103, 1313. [all data]

Peerboom, Rademaker, et al., 1992
Peerboom, R.A.L.; Rademaker, G.J.; Dekoning, L.J.; Nibbering, N.M.M., Stabilization of Cycloalkyl Carbanions in the Gas Phase, Rapid Commun. Mass Spectrom., 1992, 6, 6, 394, https://doi.org/10.1002/rcm.1290060608 . [all data]

Moran and Ellison, 1988
Moran, S.; Ellison, G.B., Photoelectron Spectroscopy of Sulfur Ions, J. Phys. Chem., 1988, 92, 7, 1794, https://doi.org/10.1021/j100318a021 . [all data]

Ingemann and Nibbering, 1985
Ingemann, S.; Nibbering, N.M.M., Gas phase chemistry of alpha-thio carbanions, Can. J. Chem., 1985, 62, 2273. [all data]

O'Hair, Bowie, et al., 1992
O'Hair, R.J.; Bowie, J.H.; Gronert, S., Gas Phase Acidity of the alpha-Amino Acids, Int. J. Mass Spectrom. Ion Proc., 1992, 117, 23, https://doi.org/10.1016/0168-1176(92)80083-D . [all data]

Bohme, Lee-Ruff, et al., 1972
Bohme, D.K.; Lee-Ruff, E.; Young, L.B., Acidity order of selected bronsted acids in the gas phase at 300K, J. Am. Chem. Soc., 1972, 94, 5153. [all data]

Taft and Topsom, 1987
Taft, R.W.; Topsom, R.D., The Nature and Analysis of Substituent Effects, Prog. Phys. Org. Chem., 1987, 16, 1. [all data]

Cumming and Kebarle, 1978
Cumming, J.B.; Kebarle, P., Summary of gas phase measurements involving acids AH. Entropy changes in proton transfer reactions involving negative ions. Bond dissociation energies D(A-H) and electron affinities EA(A), Can. J. Chem., 1978, 56, 1. [all data]


Notes

Go To: Top, Reaction thermochemistry data, References