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 151 to 200

C13H9- + Hydrogen cation = Fluorene

By formula: C13H9- + H+ = C13H10

Quantity Value Units Method Reference Comment
Δr350.5 ± 2.0kcal/molD-EARömer, Janaway, et al., 1997gas phase
Δr351.7 ± 2.1kcal/molG+TSTaft and Bordwell, 1988gas phase
Δr353.3 ± 2.6kcal/molG+TSCumming and Kebarle, 1978gas phase
Quantity Value Units Method Reference Comment
Δr342.7 ± 2.1kcal/molH-TSRömer, Janaway, et al., 1997gas phase
Δr344.0 ± 2.0kcal/molIMRETaft and Bordwell, 1988gas phase
Δr345.5 ± 2.0kcal/molIMRECumming and Kebarle, 1978gas phase

C3H5O2- + Hydrogen cation = Acetic acid, methyl ester

By formula: C3H5O2- + H+ = C3H6O2

Quantity Value Units Method Reference Comment
Δr371.8 ± 2.1kcal/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale
Δr371.8 ± 3.7kcal/molD-EAZimmerman, Reed, et al., 1977gas phase
Δr375.9 ± 3.5kcal/molEIAEPariat and Allan, 1991gas phase; From CH3CO2Me
Quantity Value Units Method Reference Comment
Δr365.1 ± 2.0kcal/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale

C6H6N- + Hydrogen cation = Aniline

By formula: C6H6N- + H+ = C6H7N

Quantity Value Units Method Reference Comment
Δr368.18 ± 0.30kcal/molD-EAWren, Vogelhuber, et al., 2012gas phase
Δr366.4 ± 2.1kcal/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale
Quantity Value Units Method Reference Comment
Δr360.91 ± 0.67kcal/molH-TSWren, Vogelhuber, et al., 2012gas phase
Δr359.1 ± 2.0kcal/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale

C4H11Si- + Hydrogen cation = Silane, tetramethyl-

By formula: C4H11Si- + H+ = C4H12Si

Quantity Value Units Method Reference Comment
Δr388.2 ± 3.1kcal/molG+TSDamrauer, Kass, et al., 1988gas phase; Comparable to fluorobenzene
Δr390.9 ± 2.0kcal/molD-EAWetzel and Brauman, 1988gas phase
Quantity Value Units Method Reference Comment
Δr379.0 ± 3.0kcal/molIMRBDamrauer, Kass, et al., 1988gas phase; Comparable to fluorobenzene
Δr381.7 ± 2.1kcal/molH-TSWetzel and Brauman, 1988gas phase
Δr390.7 ± 5.0kcal/molIMRBDePuy and Damrauer, 1984gas phase

MeS anion + Hydrogen cation = Methanethiol

By formula: CH3S- + H+ = CH4S

Quantity Value Units Method Reference Comment
Δr357.6 ± 2.0kcal/molD-EASchwartz, Davico, et al., 2000gas phase
Δr357.5 ± 2.0kcal/molD-EAMoran and Ellison, 1988gas phase
Δr356.9 ± 2.2kcal/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale
Quantity Value Units Method Reference Comment
Δr350.6 ± 2.0kcal/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale

C3H3N2- + Hydrogen cation = 1H-Pyrazole

By formula: C3H3N2- + H+ = C3H4N2

Quantity Value Units Method Reference Comment
Δr353.6 ± 2.4kcal/molG+TSGianola, Ichino, et al., 2006gas phase
Δr353.6 ± 2.4kcal/molG+TSTaft, Anvia, et al., 1986gas phase; value altered from reference due to change in acidity scale
Quantity Value Units Method Reference Comment
Δr346.4 ± 2.3kcal/molN/AGianola, Ichino, et al., 2006gas phase
Δr346.4 ± 2.3kcal/molIMRETaft, Anvia, et al., 1986gas phase; value altered from reference due to change in acidity scale

C2HClN- + Hydrogen cation = Chloromethyl cyanide

By formula: C2HClN- + H+ = C2H2ClN

Quantity Value Units Method Reference Comment
Δr357.7 ± 2.2kcal/molG+TSPoutsma, Upshaw, et al., 2002gas phase
Δr348.2 ± 6.9kcal/molEIAEHacaloglu, Suzer, et al., 1988gas phase; From ClCH2CN. ΔGacid more likely to be ca. 360 - JEB.
Quantity Value Units Method Reference Comment
Δr350.0 ± 2.0kcal/molIMRBPoutsma, Upshaw, et al., 2002gas phase
Δr341.6 ± 7.8kcal/molH-TSHacaloglu, Suzer, et al., 1988gas phase; From ClCH2CN. ΔGacid more likely to be ca. 360 - JEB.

C9H11O- + Hydrogen cation = p-Cumenol

By formula: C9H11O- + H+ = C9H12O

Quantity Value Units Method Reference Comment
Δr349.2 ± 2.1kcal/molG+TSFujio, McIver, et al., 1981gas phase; ΔHf(AH) disagrees with group additivity by 8.6 kcal/mol (-41.4 kcal/mol; value altered from reference due to change in acidity scale
Quantity Value Units Method Reference Comment
Δr342.4 ± 2.0kcal/molIMREFujio, McIver, et al., 1981gas phase; ΔHf(AH) disagrees with group additivity by 8.6 kcal/mol (-41.4 kcal/mol; value altered from reference due to change in acidity scale

C7H15O- + Hydrogen cation = 2-Hexanol, 2-methyl-

By formula: C7H15O- + H+ = C7H16O

Quantity Value Units Method Reference Comment
Δr371.7 ± 2.1kcal/molG+TSHiggins and Bartmess, 1998gas phase
Δr371.6 ± 2.8kcal/molG+TSBoand, Houriet, et al., 1983gas phase; value altered from reference due to change in acidity scale
Quantity Value Units Method Reference Comment
Δr365.1 ± 2.0kcal/molIMREHiggins and Bartmess, 1998gas phase
Δr365.0 ± 2.7kcal/molCIDCBoand, Houriet, et al., 1983gas phase; value altered from reference due to change in acidity scale

C6H4FO- + Hydrogen cation = Phenol, 2-fluoro-

By formula: C6H4FO- + H+ = C6H5FO

Quantity Value Units Method Reference Comment
Δr345.3 ± 2.2kcal/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Δr345.8 ± 2.9kcal/molG+TSKebarle and McMahon, 1977gas phase
Quantity Value Units Method Reference Comment
Δr339.0 ± 2.0kcal/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Δr339.5 ± 2.0kcal/molIMREKebarle and McMahon, 1977gas phase

C6H5O2- + Hydrogen cation = 1,2-Benzenediol

By formula: C6H5O2- + H+ = C6H6O2

Quantity Value Units Method Reference Comment
Δr339.5 ± 2.1kcal/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Δr339.8 ± 2.6kcal/molG+TSKebarle and McMahon, 1977gas phase
Quantity Value Units Method Reference Comment
Δr332.7 ± 2.0kcal/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Δr332.9 ± 2.0kcal/molIMREKebarle and McMahon, 1977gas phase

C7H4NO- + Hydrogen cation = Benzonitrile, 2-hydroxy-

By formula: C7H4NO- + H+ = C7H5NO

Quantity Value Units Method Reference Comment
Δr334.5 ± 2.2kcal/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Δr334.7 ± 2.9kcal/molG+TSKebarle and McMahon, 1977gas phase
Quantity Value Units Method Reference Comment
Δr327.1 ± 2.0kcal/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Δr327.2 ± 2.0kcal/molIMREKebarle and McMahon, 1977gas phase

C6H6NO- + Hydrogen cation = Phenol, 3-amino-

By formula: C6H6NO- + H+ = C6H7NO

Quantity Value Units Method Reference Comment
Δr350.5 ± 2.1kcal/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Δr351.2 ± 2.3kcal/molG+TSKebarle and McMahon, 1977gas phase
Quantity Value Units Method Reference Comment
Δr343.7 ± 2.0kcal/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Δr344.3 ± 2.0kcal/molIMREKebarle and McMahon, 1977gas phase

C6H6NO- + Hydrogen cation = Phenol, 4-amino-

By formula: C6H6NO- + H+ = C6H7NO

Quantity Value Units Method Reference Comment
Δr352.5 ± 2.1kcal/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Δr354.5 ± 2.3kcal/molG+TSKebarle and McMahon, 1977gas phase
Quantity Value Units Method Reference Comment
Δr345.6 ± 2.0kcal/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Δr347.6 ± 2.0kcal/molIMREKebarle and McMahon, 1977gas phase

C6H5O2- + Hydrogen cation = Resorcinol

By formula: C6H5O2- + H+ = C6H6O2

Quantity Value Units Method Reference Comment
Δr346.6 ± 2.1kcal/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Δr345.2 ± 2.6kcal/molG+TSKebarle and McMahon, 1977gas phase
Quantity Value Units Method Reference Comment
Δr339.8 ± 2.0kcal/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Δr338.3 ± 2.0kcal/molIMREKebarle and McMahon, 1977gas phase

C6H4FO- + Hydrogen cation = Phenol, 4-fluoro-

By formula: C6H4FO- + H+ = C6H5FO

Quantity Value Units Method Reference Comment
Δr346.7 ± 2.1kcal/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Δr347.7 ± 2.3kcal/molG+TSKebarle and McMahon, 1977gas phase
Quantity Value Units Method Reference Comment
Δr339.9 ± 2.0kcal/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Δr340.8 ± 2.0kcal/molIMREKebarle and McMahon, 1977gas phase

C7H4NO- + Hydrogen cation = Benzonitrile, 3-hydroxy-

By formula: C7H4NO- + H+ = C7H5NO

Quantity Value Units Method Reference Comment
Δr335.7 ± 2.1kcal/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Δr335.9 ± 2.3kcal/molG+TSKebarle and McMahon, 1977gas phase
Quantity Value Units Method Reference Comment
Δr328.9 ± 2.0kcal/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Δr329.0 ± 2.0kcal/molIMREKebarle and McMahon, 1977gas phase

C7H4NO- + Hydrogen cation = Benzonitrile, 4-hydroxy-

By formula: C7H4NO- + H+ = C7H5NO

Quantity Value Units Method Reference Comment
Δr332.1 ± 2.1kcal/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Δr332.6 ± 2.6kcal/molG+TSKebarle and McMahon, 1977gas phase
Quantity Value Units Method Reference Comment
Δr325.3 ± 2.0kcal/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Δr325.7 ± 2.0kcal/molIMREKebarle and McMahon, 1977gas phase

C7H7O2- + Hydrogen cation = m-Guaiacol

By formula: C7H7O2- + H+ = C7H8O2

Quantity Value Units Method Reference Comment
Δr348.0 ± 2.1kcal/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Δr348.8 ± 2.3kcal/molG+TSKebarle and McMahon, 1977gas phase
Quantity Value Units Method Reference Comment
Δr341.1 ± 2.0kcal/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Δr341.9 ± 2.0kcal/molIMREKebarle and McMahon, 1977gas phase

C7H7O2- + Hydrogen cation = Mequinol

By formula: C7H7O2- + H+ = C7H8O2

Quantity Value Units Method Reference Comment
Δr350.3 ± 2.1kcal/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Δr351.1 ± 2.3kcal/molG+TSKebarle and McMahon, 1977gas phase
Quantity Value Units Method Reference Comment
Δr343.5 ± 2.0kcal/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Δr344.2 ± 2.0kcal/molIMREKebarle and McMahon, 1977gas phase

C6H4NO3- + Hydrogen cation = Phenol, 3-nitro-

By formula: C6H4NO3- + H+ = C6H5NO3

Quantity Value Units Method Reference Comment
Δr334.3 ± 2.1kcal/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Δr334.6 ± 2.6kcal/molG+TSKebarle and McMahon, 1977gas phase
Quantity Value Units Method Reference Comment
Δr327.5 ± 2.0kcal/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Δr327.7 ± 2.0kcal/molIMREKebarle and McMahon, 1977gas phase

C7H7O- + Hydrogen cation = Phenol, 2-methyl-

By formula: C7H7O- + H+ = C7H8O

Quantity Value Units Method Reference Comment
Δr349.5 ± 2.2kcal/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Δr350.2 ± 2.9kcal/molG+TSKebarle and McMahon, 1977gas phase
Quantity Value Units Method Reference Comment
Δr342.0 ± 2.0kcal/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Δr342.7 ± 2.0kcal/molIMREKebarle and McMahon, 1977gas phase

C8H13O2- + Hydrogen cation = Cyclohexaneacetic acid

By formula: C8H13O2- + H+ = C8H14O2

Quantity Value Units Method Reference Comment
Δr345.3 ± 2.1kcal/molG+TSCaldwell, Renneboog, et al., 1989gas phase
Δr345.2 ± 2.1kcal/molG+TSJinfeng, Topsom, et al., 1988gas phase; value altered from reference due to change in acidity scale
Quantity Value Units Method Reference Comment
Δr338.3 ± 2.0kcal/molIMRECaldwell, Renneboog, et al., 1989gas phase
Δr338.2 ± 2.0kcal/molIMREJinfeng, Topsom, et al., 1988gas phase; value altered from reference due to change in acidity scale

C2H3S- + Hydrogen cation = Thioacetaldehyde

By formula: C2H3S- + H+ = C2H4S

Quantity Value Units Method Reference Comment
Δr347.8 ± 3.4kcal/molG+TSZhang and Grabowski, 1989gas phase; Between MeCO2H, EtCO2H (Acid = MeCH=S)
Δr349.1 ± 4.1kcal/molG+TSGuillemin, Riague, et al., 2005gas phase; Acid: CH3CH=S
Quantity Value Units Method Reference Comment
Δr341.0 ± 3.0kcal/molIMRBZhang and Grabowski, 1989gas phase; Between MeCO2H, EtCO2H (Acid = MeCH=S)
Δr342.3 ± 3.8kcal/molIMRBGuillemin, Riague, et al., 2005gas phase; Acid: CH3CH=S

C11H15O2- + Hydrogen cation = Adamantane-1-carboxylic acid

By formula: C11H15O2- + H+ = C11H16O2

Quantity Value Units Method Reference Comment
Δr343.0 ± 2.1kcal/molG+TSCaldwell, Renneboog, et al., 1989gas phase
Δr343.6 ± 2.1kcal/molG+TSJinfeng, Topsom, et al., 1988gas phase; value altered from reference due to change in acidity scale
Quantity Value Units Method Reference Comment
Δr336.0 ± 2.0kcal/molIMRECaldwell, Renneboog, et al., 1989gas phase
Δr336.6 ± 2.0kcal/molIMREJinfeng, Topsom, et al., 1988gas phase; value altered from reference due to change in acidity scale

C8H7O2- + Hydrogen cation = Benzeneacetic acid

By formula: C8H7O2- + H+ = C8H8O2

Quantity Value Units Method Reference Comment
Δr341.5 ± 2.1kcal/molG+TSCaldwell, Renneboog, et al., 1989gas phase
Δr341.1 ± 2.1kcal/molG+TSJinfeng, Topsom, et al., 1988gas phase; value altered from reference due to change in acidity scale
Quantity Value Units Method Reference Comment
Δr334.5 ± 2.0kcal/molIMRECaldwell, Renneboog, et al., 1989gas phase
Δr334.1 ± 2.0kcal/molIMREJinfeng, Topsom, et al., 1988gas phase; value altered from reference due to change in acidity scale

C5H9O2- + Hydrogen cation = Propanoic acid, 2,2-dimethyl-

By formula: C5H9O2- + H+ = C5H10O2

Quantity Value Units Method Reference Comment
Δr344.6 ± 2.1kcal/molG+TSCaldwell, Renneboog, et al., 1989gas phase
Δr345.0 ± 2.1kcal/molG+TSJinfeng, Topsom, et al., 1988gas phase; value altered from reference due to change in acidity scale
Quantity Value Units Method Reference Comment
Δr337.6 ± 2.0kcal/molIMRECaldwell, Renneboog, et al., 1989gas phase
Δr338.0 ± 2.0kcal/molIMREJinfeng, Topsom, et al., 1988gas phase; value altered from reference due to change in acidity scale

C4H3N2- + Hydrogen cation = Pyrazine

By formula: C4H3N2- + H+ = C4H4N2

Quantity Value Units Method Reference Comment
Δr392.6 ± 2.5kcal/molTDEqMeot-ner and Kafafi, 1988gas phase; anchored to 88MEO scale, not the "87 acidity scale". The Kiefer, Zhang, et al., 1997 BDE is for ortho.
Quantity Value Units Method Reference Comment
Δr383.50 ± 0.40kcal/molN/AWren, Vogelhuber, et al., 2012, 2gas phase
Δr383.1 ± 2.0kcal/molTDEqMeot-ner and Kafafi, 1988gas phase; anchored to 88MEO scale, not the "87 acidity scale". The Kiefer, Zhang, et al., 1997 BDE is for ortho.

Iodide + Hydrogen cation = Hydrogen iodide

By formula: I- + H+ = HI

Quantity Value Units Method Reference Comment
Δr314.350 ± 0.020kcal/molD-EAPelaez, Blondel, et al., 2009gas phase; Given: 3.0590463(38) eV
Δr313.60kcal/molN/ACheck, Faust, et al., 2001gas phase; Fe(CO)2-(q); ; ΔS(EA)=5.0
Quantity Value Units Method Reference Comment
Δr309.280 ± 0.060kcal/molH-TSPelaez, Blondel, et al., 2009gas phase; Given: 3.0590463(38) eV
Δr308.50kcal/molN/ACheck, Faust, et al., 2001gas phase; Fe(CO)2-(q); ; ΔS(EA)=5.0

C9H12BrO2- + Hydrogen cation = C9H13BrO2

By formula: C9H12BrO2- + H+ = C9H13BrO2

Quantity Value Units Method Reference Comment
Δr337.3 ± 2.2kcal/molG+TSKoppel, Mishima, et al., 1993gas phase
Δr337.3 ± 2.2kcal/molG+TSTaft and Topsom, 1987gas phase; value altered from reference due to change in acidity scale
Quantity Value Units Method Reference Comment
Δr330.3 ± 2.0kcal/molIMREKoppel, Mishima, et al., 1993gas phase
Δr330.3 ± 2.0kcal/molIMRETaft and Topsom, 1987gas phase; value altered from reference due to change in acidity scale

H5Si2- + Hydrogen cation = Disilane

By formula: H5Si2- + H+ = H6Si2

Quantity Value Units Method Reference Comment
Δr<313.5 ± 2.8kcal/molAcidKrishnakumar and Srivastava, 1991gas phase; From Si2H6, AP = 0.0 eV/Data for SiH4 plus a-Si effects imply ΔHacid ca. 360. G3MP2B3 calculations give dHacid=360 kcal/mol
Quantity Value Units Method Reference Comment
Δr<304.7 ± 3.4kcal/molH-TSKrishnakumar and Srivastava, 1991gas phase; From Si2H6, AP = 0.0 eV/Data for SiH4 plus a-Si effects imply ΔHacid ca. 360. G3MP2B3 calculations give dHacid=360 kcal/mol

C8H17O2- + Hydrogen cation = Heptanoic acid, 2-ethyl-

By formula: C8H17O2- + H+ = C9H18O2

Quantity Value Units Method Reference Comment
Δr338.4 ± 2.0kcal/molTDEqNorrman and McMahon, 1999gas phase; folded form. dSacid = 11.2 eu
Δr345.7 ± 2.0kcal/molTDEqNorrman and McMahon, 1999gas phase; Unfolded form
Quantity Value Units Method Reference Comment
Δr335.1 ± 2.1kcal/molH-TSNorrman and McMahon, 1999gas phase; folded form. dSacid = 11.2 eu
Δr337.4 ± 2.1kcal/molH-TSNorrman and McMahon, 1999gas phase; Unfolded form

C3H5O- + Hydrogen cation = Propanal

By formula: C3H5O- + H+ = C3H6O

Quantity Value Units Method Reference Comment
Δr365.2 ± 2.1kcal/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale
Δr366.0 ± 2.4kcal/molG+TSCumming and Kebarle, 1978gas phase
Quantity Value Units Method Reference Comment
Δr358.7 ± 2.0kcal/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale
Δr359.4 ± 2.0kcal/molIMRECumming and Kebarle, 1978gas phase

C9H9O- + Hydrogen cation = Benzyl methyl ketone

By formula: C9H9O- + H+ = C9H10O

Quantity Value Units Method Reference Comment
Δr350.2 ± 2.5kcal/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale
Δr351.1 ± 3.5kcal/molG+TSCumming and Kebarle, 1978gas phase
Quantity Value Units Method Reference Comment
Δr344.5 ± 2.0kcal/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale
Δr345.4 ± 2.0kcal/molIMRECumming and Kebarle, 1978gas phase

C5H4F3O2- + Hydrogen cation = 2,4-Pentanedione, 1,1,1-trifluoro-

By formula: C5H4F3O2- + H+ = C5H5F3O2

Quantity Value Units Method Reference Comment
Δr328.3 ± 2.9kcal/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Δr328.5 ± 4.1kcal/molG+TSCumming and Kebarle, 1978gas phase
Quantity Value Units Method Reference Comment
Δr322.0 ± 2.0kcal/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Δr322.1 ± 2.0kcal/molIMRECumming and Kebarle, 1978gas phase

C8H6N- + Hydrogen cation = Benzyl nitrile

By formula: C8H6N- + H+ = C8H7N

Quantity Value Units Method Reference Comment
Δr350.7 ± 2.3kcal/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Δr351.5 ± 3.2kcal/molG+TSCumming and Kebarle, 1978gas phase
Quantity Value Units Method Reference Comment
Δr344.1 ± 2.0kcal/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Δr344.9 ± 2.0kcal/molIMRECumming and Kebarle, 1978gas phase

C13H11- + Hydrogen cation = Diphenylmethane

By formula: C13H11- + H+ = C13H12

Quantity Value Units Method Reference Comment
Δr363.6 ± 2.1kcal/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale
Δr361.3 ± 2.3kcal/molG+TSCumming and Kebarle, 1978gas phase
Quantity Value Units Method Reference Comment
Δr358.2 ± 2.0kcal/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale
Δr355.9 ± 2.0kcal/molIMRECumming and Kebarle, 1978gas phase

C4H6ClO2- + Hydrogen cation = Butanoic acid, 2-chloro-

By formula: C4H6ClO2- + H+ = C4H7ClO2

Quantity Value Units Method Reference Comment
Δr337.1 ± 2.1kcal/molG+TSCaldwell, Renneboog, et al., 1989gas phase; dHf(AH) from GpAd in Stein, Rikkers, et al. is seriously in error
Δr337.5 ± 2.3kcal/molG+TSCumming and Kebarle, 1978gas phase
Quantity Value Units Method Reference Comment
Δr330.5 ± 2.0kcal/molIMRECaldwell, Renneboog, et al., 1989gas phase; dHf(AH) from GpAd in Stein, Rikkers, et al. is seriously in error
Δr330.9 ± 2.0kcal/molIMRECumming and Kebarle, 1978gas phase

C9H9O- + Hydrogen cation = 1-Propanone, 1-phenyl-

By formula: C9H9O- + H+ = C9H10O

Quantity Value Units Method Reference Comment
Δr360.5 ± 2.1kcal/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale
Δr360.7 ± 5.0kcal/molG+TSCumming and Kebarle, 1978gas phase
Quantity Value Units Method Reference Comment
Δr353.9 ± 2.0kcal/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale
Δr354.1 ± 2.0kcal/molIMRECumming and Kebarle, 1978gas phase

C2H4NO2- + Hydrogen cation = Ethane, nitro-

By formula: C2H4NO2- + H+ = C2H5NO2

Quantity Value Units Method Reference Comment
Δr355.9 ± 2.2kcal/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale
Δr357.5 ± 2.9kcal/molG+TSCumming and Kebarle, 1978gas phase
Quantity Value Units Method Reference Comment
Δr349.5 ± 2.0kcal/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale
Δr351.0 ± 2.0kcal/molIMRECumming and Kebarle, 1978gas phase

C3H6NO2- + Hydrogen cation = Propane, 2-nitro-

By formula: C3H6NO2- + H+ = C3H7NO2

Quantity Value Units Method Reference Comment
Δr356.0 ± 2.2kcal/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale
Δr356.4 ± 2.9kcal/molG+TSCumming and Kebarle, 1978gas phase
Quantity Value Units Method Reference Comment
Δr350.0 ± 2.0kcal/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale
Δr350.3 ± 2.0kcal/molIMRECumming and Kebarle, 1978gas phase

C2H5OS- + Hydrogen cation = Dimethyl Sulfoxide

By formula: C2H5OS- + H+ = C2H6OS

Quantity Value Units Method Reference Comment
Δr373.5 ± 2.1kcal/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale
Δr374.3 ± 2.3kcal/molG+TSCumming and Kebarle, 1978gas phase
Quantity Value Units Method Reference Comment
Δr366.4 ± 2.0kcal/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale
Δr367.2 ± 2.0kcal/molIMRECumming and Kebarle, 1978gas phase

C2H5O2S- + Hydrogen cation = Dimethyl sulfone

By formula: C2H5O2S- + H+ = C2H6O2S

Quantity Value Units Method Reference Comment
Δr365.8 ± 2.2kcal/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale
Δr366.5 ± 2.9kcal/molG+TSCumming and Kebarle, 1978gas phase
Quantity Value Units Method Reference Comment
Δr358.2 ± 2.0kcal/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale
Δr358.9 ± 2.0kcal/molIMRECumming and Kebarle, 1978gas phase

C3H4ClO2- + Hydrogen cation = Propanoic acid, 2-chloro-

By formula: C3H4ClO2- + H+ = C3H5ClO2

Quantity Value Units Method Reference Comment
Δr337.0 ± 2.1kcal/molG+TSCaldwell, Renneboog, et al., 1989gas phase; dHf(AH) from GpAd in Stein, Rikkers, et al. is seriously in error
Δr336.4 ± 2.3kcal/molG+TSCumming and Kebarle, 1978gas phase
Quantity Value Units Method Reference Comment
Δr330.4 ± 2.0kcal/molIMRECaldwell, Renneboog, et al., 1989gas phase; dHf(AH) from GpAd in Stein, Rikkers, et al. is seriously in error
Δr329.8 ± 2.0kcal/molIMRECumming and Kebarle, 1978gas phase

C10H19O2- + Hydrogen cation = n-Decanoic acid

By formula: C10H19O2- + H+ = C10H20O2

Quantity Value Units Method Reference Comment
Δr338.8 ± 2.0kcal/molTDEqNorrman and McMahon, 1999gas phase; Folded form; dSacid = 7.2 eu
Δr346.1 ± 2.0kcal/molTDEqNorrman and McMahon, 1999gas phase; Unfolded form
Quantity Value Units Method Reference Comment
Δr336.7 ± 2.1kcal/molH-TSNorrman and McMahon, 1999gas phase; Folded form; dSacid = 7.2 eu
Δr338.8 ± 2.1kcal/molH-TSNorrman and McMahon, 1999gas phase; Unfolded form

C7H4F3- + Hydrogen cation = Benzene, (trifluoromethyl)-

By formula: C7H4F3- + H+ = C7H5F3

Quantity Value Units Method Reference Comment
Δr387.1 ± 2.5kcal/molTDEqMeot-ner and Kafafi, 1988gas phase; anchored to 88MEO scale, not the "87 acidity scale". The Kiefer, Zhang, et al., 1997 BDE is for ortho.
Quantity Value Units Method Reference Comment
Δr378.6 ± 2.0kcal/molTDEqMeot-ner and Kafafi, 1988gas phase; anchored to 88MEO scale, not the "87 acidity scale". The Kiefer, Zhang, et al., 1997 BDE is for ortho.
Δr379.0 ± 5.0kcal/molIMRBBartmess and McIver Jr., 1979gas phase

C3H6N- + Hydrogen cation = C3H7N

By formula: C3H6N- + H+ = C3H7N

Quantity Value Units Method Reference Comment
Δr380.7 ± 4.2kcal/molG+TSDahlke and Kass, 1991gas phase; From CH2=CHCH2NH2 + HO-. Between MeOH, EtOH in acidity. Reprotonation structure uncertain.Acid take as EtCH=NH for this acidity.
Quantity Value Units Method Reference Comment
Δr372.5 ± 4.0kcal/molIMRBDahlke and Kass, 1991gas phase; From CH2=CHCH2NH2 + HO-. Between MeOH, EtOH in acidity. Reprotonation structure uncertain.Acid take as EtCH=NH for this acidity.

C3H9OSi- + Hydrogen cation = Silanol, trimethyl-

By formula: C3H9OSi- + H+ = C3H10OSi

Quantity Value Units Method Reference Comment
Δr362.9 ± 4.6kcal/molG+TSAngelini, Johnson, et al., 1991gas phase; Between CF2HCH2OH, CF3CH2OH
Δr358.9 ± 4.1kcal/molG+TSDamrauer, Simon, et al., 1991gas phase; between pyrrole, CF3CH2OH
Quantity Value Units Method Reference Comment
Δr356.5 ± 4.5kcal/molIMRBAngelini, Johnson, et al., 1991gas phase; Between CF2HCH2OH, CF3CH2OH
Δr352.5 ± 4.0kcal/molIMRBDamrauer, Simon, et al., 1991gas phase; between pyrrole, CF3CH2OH

C3H2N- + Hydrogen cation = 2-Propenenitrile

By formula: C3H2N- + H+ = C3H3N

Quantity Value Units Method Reference Comment
Δr371.1 ± 2.2kcal/molG+TSBartmess, 1980gas phase; value altered from reference due to change in acidity scale
Δr364.3 ± 4.6kcal/molEIAEHeni and Illenberger, 1986gas phase; From CH2=CHCN. G3MP2B3 calculations indicate a dHacdi ca. 374 kcal/mol
Quantity Value Units Method Reference Comment
Δr365.3 ± 2.0kcal/molIMREBartmess, 1980gas phase; value altered from reference due to change in acidity scale

C7H4NO4- + Hydrogen cation = Benzoic acid, 3-nitro-

By formula: C7H4NO4- + H+ = C7H5NO4

Quantity Value Units Method Reference Comment
Δr329.0 ± 2.1kcal/molG+TSTaft, 1987gas phase; value altered from reference due to change in acidity scale
Δr329.1 ± 2.1kcal/molG+TSKebarle and McMahon, 1977gas phase
Quantity Value Units Method Reference Comment
Δr322.0 ± 2.0kcal/molIMRETaft, 1987gas phase; value altered from reference due to change in acidity scale
Δr322.1 ± 2.0kcal/molIMREKebarle and McMahon, 1977gas phase

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.

Römer, Janaway, et al., 1997
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Taft and Bordwell, 1988
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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]

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]

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]

Pariat and Allan, 1991
Pariat, Y.; Allan, M., Dissociative Attachment to Methyl Acetate: Evidence for Ion/Molecule Complexes as Intermediates, Int. J. Mass Spectrom. Ion Proc., 1991, 103, 2-3, 181, https://doi.org/10.1016/0168-1176(91)80088-5 . [all data]

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Damrauer, Kass, et al., 1988
Damrauer, R.; Kass, S.R.; DePuy, C.H., Gas-Phase Acidities of Methylsilanes: C-H versus Si-H, Organomet., 1988, 7, 3, 637, https://doi.org/10.1021/om00093a011 . [all data]

Wetzel and Brauman, 1988
Wetzel, D.M.; Brauman, J.I., Quantitative Measure of alpha-Silyl Carbanion Stabilization. The Electron Affinity of (Trimethylsilyl)methyl Radical, J. Am. Chem. Soc., 1988, 110, 25, 8333, https://doi.org/10.1021/ja00233a008 . [all data]

DePuy and Damrauer, 1984
DePuy, C.H.; Damrauer, R., Reactions of organosilane anionic species with nitrous oxide, Organometallics, 1984, 3, 362. [all data]

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Schwartz, R.L.; Davico, G.E.; Lineberger, W.C., Negative-ion photoelectron spectroscopy of CH3S-, J. Electron Spectros. Rel. Phenom., 2000, 108, 1-3, 163-168, https://doi.org/10.1016/S0368-2048(00)00125-0 . [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]

Gianola, Ichino, et al., 2006
Gianola, A.J.; Ichino, T.; Kato, S.; Bierbaum, V.M.; Lineberger, W.C., Thermochemical studies of pyrazolide, J. Phys. Chem. A, 2006, 110, 27, 8457-8466, https://doi.org/10.1021/jp057499+ . [all data]

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Taft, R.W.; Anvia, F.; Taagepera, M.; Catalan, J.; Elgueroy, J., Electrostatic proximity effects in the relative basicities of pyrazole, imidazole, pyridazine, and pyrimidine, J. Am. Chem. Soc., 1986, 108, 3237. [all data]

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Fujio, McIver, et al., 1981
Fujio, M.; McIver, R.T., Jr.; Taft, R.W., Effects on the acidities of phenols from specific substituent-solvent interactions. Inherent substituent parameters from gas phase acidities, J. Am. Chem. Soc., 1981, 103, 4017. [all data]

Higgins and Bartmess, 1998
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Boand, Houriet, et al., 1983
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Kebarle and McMahon, 1977
Kebarle, P.; McMahon, T.B., Intrinsic Acidities of Substituted Phenols and Benzoic Acids Determined by Gas Phase Proton Transfer Equilibria, J. Am. Chem. Soc., 1977, 99, 7, 2222, https://doi.org/10.1021/ja00449a032 . [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]

Jinfeng, Topsom, et al., 1988
Jinfeng, C.; Topsom, R.D.; Headley, A.D.; Koppel, I.; Mishima, M.; Taft, R.W.; Veji, S., Acidities of Substituted Acetic Acids, J. Mol. Struct., 1988, 168, 141, https://doi.org/10.1016/0166-1280(88)80349-X . [all data]

Zhang and Grabowski, 1989
Zhang, L.; Grabowski, J.J., The Gas-Phase Basicity and H/D Exchange Characteristics of the Parent Thiocarbonyl Enolate Anions, J. Chem. Soc. Chem. Comm. 1819, 1989. [all data]

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Guillemin, J.C.; Riague, E.H.; Gal, J.F.; Maria, P.C.; Mo, O.; Yanez, M., Acidity trends in alpha,beta-unsaturated sulfur, selenium, and tellurium derivatives: Comparison with C-, Si-, Ge-, Sn-, N-, P-, As-, and Sb-containing analogues, Chem. Eur. J., 2005, 11, 7, 2145-2153, https://doi.org/10.1002/chem.200400989 . [all data]

Meot-ner and Kafafi, 1988
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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]

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Wren, S.W.; Vogelhuber, K.M.; Garver, J.M.; Kato, S.; Sheps, L.; Bierbaum, V.M.; Lineberger, W.C., C-H Bond Strengths and Acidities in Aromatic Systems: Effects of Nitrogen Incorporation in Mono-, Di-, and Triazines, J. Am. Chem. Soc., 2012, 134, 15, 6584-6595, https://doi.org/10.1021/ja209566q . [all data]

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Koppel, I.A.; Mishima, M.; Stock, L.M.; Taft, R.W.; Topsom, R.D., Acidities of 4-Substituted Benzoic, Bicyclo[2.2.2]Oct-1-yl and Bicyclo[2.2.2]Oct-2-enyl Carboxylic Acids, J. Phys. Org. Chem., 1993, 6, 12, 685, https://doi.org/10.1002/poc.610061205 . [all data]

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Krishnakumar, E.; Srivastava, S.K., Dissociative Electron Attachment of Electrons with Si2H6, Int. J. Mass Spectrom. Ion Proc., 1991, 103, 2-3, 107, https://doi.org/10.1016/0168-1176(91)80082-X . [all data]

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Norrman, K.; McMahon, T.B., Intramolecular solvation of carboxylate anions in the gas phase, J. Phys. Chem. A, 1999, 103, 35, 7008-7016, https://doi.org/10.1021/jp9908202 . [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]

Bartmess and McIver Jr., 1979
Bartmess, J.E.; McIver Jr., The Gas Phase Acidity Scale in Gas Phase Ion Chemistry, Gas Phase Ion Chemistry, V. 2, M.T. Bowers, Ed., Academic Press, NY, 1979, Ch. 11, Elsevier, 1979. [all data]

Dahlke and Kass, 1991
Dahlke, G.D.; Kass, S.R., Substituent Effects in the Gas Phase - 1-Substituted Allyl Anions, J. Am. Chem. Soc., 1991, 113, 15, 5566, https://doi.org/10.1021/ja00015a008 . [all data]

Angelini, Johnson, et al., 1991
Angelini, G.; Johnson, C.E.; Brauman, J.I., Addition and Deprotonation in Reactions of Hydroxide Ion with a beta-Hydroxysilane, Int. J. Mass Spectrom. Ion Proc., 1991, 109, 1, https://doi.org/10.1016/0168-1176(91)85093-2 . [all data]

Damrauer, Simon, et al., 1991
Damrauer, R.; Simon, R.; Krempp, M., Effect of Substituents on the Gas-Phase Acidity of Silanols, J. Am. Chem. Soc., 1991, 113, 12, 4431, https://doi.org/10.1021/ja00012a009 . [all data]

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Heni and Illenberger, 1986
Heni, M.; Illenberger, E., Electron attachment by saturated nitriles. Acrylonitrile (CH2H3CN), and benzonitrile (C6H5CN), Int. J. Mass Spectrom. Ion Phys., 1986, 73, 127. [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]


Notes

Go To: Top, Reaction thermochemistry data, References