Hydrogen cation

Formula: H⁺
Molecular weight: 1.00739
IUPAC Standard InChI: InChI=1S/p+1
IUPAC Standard InChIKey: GPRLSGONYQIRFK-UHFFFAOYSA-N
CAS Registry Number: 12408-02-5
Chemical structure:
This structure is also available as a 2d Mol file
Isotopologues:
- Deuterium cation
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Reaction thermochemistry data

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Reactions 451 to 500

C₈H₉^- + Hydrogen cation =

By formula: C₈H₉^- + H⁺ = C₈H₁₀

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	379.7 ± 2.1	kcal/mol	G+TS	Bartmess, Scott, et al., 1979	gas phase; value altered from reference due to change in acidity scale
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	373.3 ± 2.0	kcal/mol	IMRE	Bartmess, Scott, et al., 1979	gas phase; value altered from reference due to change in acidity scale

C₈H₉^- + Hydrogen cation =

By formula: C₈H₉^- + H⁺ = C₈H₁₀

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	381.9 ± 2.4	kcal/mol	G+TS	Bartmess, Scott, et al., 1979	gas phase; value altered from reference due to change in acidity scale
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	374.8 ± 2.3	kcal/mol	IMRE	Bartmess, Scott, et al., 1979	gas phase; value altered from reference due to change in acidity scale

C₈H₆N^- + Hydrogen cation =

By formula: C₈H₆N^- + H⁺ = C₈H₇N

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	360.5 ± 2.4	kcal/mol	G+TS	Kahn, Hehre, et al., 1984	gas phase; value altered from reference due to change in acidity scale
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	353.3 ± 2.3	kcal/mol	IMRE	Kahn, Hehre, et al., 1984	gas phase; value altered from reference due to change in acidity scale

C₈H₇O^- + Hydrogen cation =

By formula: C₈H₇O^- + H⁺ = C₈H₈O

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	359.7 ± 2.4	kcal/mol	G+TS	Kahn, Hehre, et al., 1984	gas phase; value altered from reference due to change in acidity scale
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	352.6 ± 2.3	kcal/mol	IMRE	Kahn, Hehre, et al., 1984	gas phase; value altered from reference due to change in acidity scale

C₄H₄N^- + Hydrogen cation =

By formula: C₄H₄N^- + H⁺ = C₄H₅N

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	370.7 ± 2.1	kcal/mol	G+TS	Bartmess and Burnham, 1984	gas phase; value altered from reference due to change in acidity scale
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	364.1 ± 2.0	kcal/mol	IMRE	Bartmess and Burnham, 1984	gas phase; value altered from reference due to change in acidity scale

C₇H₇^- + Hydrogen cation =

By formula: C₇H₇^- + H⁺ = C₇H₈

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	375.2 ± 2.2	kcal/mol	G+TS	Bartmess, Scott, et al., 1979	gas phase; value altered from reference due to change in acidity scale
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	369.2 ± 2.0	kcal/mol	IMRE	Bartmess, Scott, et al., 1979	gas phase; value altered from reference due to change in acidity scale

C₄H₄F₃^- + Hydrogen cation =

By formula: C₄H₄F₃^- + H⁺ = C₄H₅F₃

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	374.0 ± 2.1	kcal/mol	G+TS	Bartmess and Burnham, 1984	gas phase; value altered from reference due to change in acidity scale
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	367.4 ± 2.0	kcal/mol	IMRE	Bartmess and Burnham, 1984	gas phase; value altered from reference due to change in acidity scale

C₅H₇^- + Hydrogen cation =

By formula: C₅H₇^- + H⁺ = C₅H₈

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	379.7 ± 2.5	kcal/mol	G+TS	Bartmess, Scott, et al., 1979	gas phase; value altered from reference due to change in acidity scale
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	372.0 ± 2.0	kcal/mol	IMRE	Bartmess, Scott, et al., 1979	gas phase; value altered from reference due to change in acidity scale

C₆H₉^- + Hydrogen cation =

By formula: C₆H₉^- + H⁺ = C₆H₁₀

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	378.0 ± 2.2	kcal/mol	G+TS	Bartmess, Scott, et al., 1979	gas phase; value altered from reference due to change in acidity scale
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	370.2 ± 2.0	kcal/mol	IMRE	Bartmess, Scott, et al., 1979	gas phase; value altered from reference due to change in acidity scale

C₇H₇S^- + Hydrogen cation =

By formula: C₇H₇S^- + H⁺ = C₇H₈S

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	386.3 ± 5.1	kcal/mol	G+TS	Ingemann and Nibbering, 1985	gas phase; value altered from reference due to change in acidity scale
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	379.0 ± 5.0	kcal/mol	IMRB	Ingemann and Nibbering, 1985	gas phase; value altered from reference due to change in acidity scale

C₇H₇S^- + Hydrogen cation =

By formula: C₇H₇S^- + H⁺ = C₇H₈S

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	381.5 ± 2.1	kcal/mol	G+TS	Ingemann and Nibbering, 1985	gas phase; value altered from reference due to change in acidity scale
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	374.2 ± 2.0	kcal/mol	IMRE	Ingemann and Nibbering, 1985	gas phase; value altered from reference due to change in acidity scale

+ Hydrogen cation =

By formula: C₇H₉^- + H⁺ = C₇H₁₀

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	402.1 ± 3.1	kcal/mol	G+TS	Lee and Squires, 1986	gas phase; Between NH₃, EtNH₂. Assigned as vinylic site by authors.
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	393.9 ± 3.0	kcal/mol	IMRB	Lee and Squires, 1986	gas phase; Between NH₃, EtNH₂. Assigned as vinylic site by authors.

C₉H₃F₆O₂^- + Hydrogen cation =

By formula: C₉H₃F₆O₂^- + H⁺ = C₉H₄F₆O₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	324.4 ± 2.1	kcal/mol	G+TS	Jinfeng, Topsom, et al., 1988	gas phase; value altered from reference due to change in acidity scale
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	317.4 ± 2.0	kcal/mol	IMRE	Jinfeng, Topsom, et al., 1988	gas phase; value altered from reference due to change in acidity scale

C₃H₆NS^- + Hydrogen cation =

By formula: C₃H₆NS^- + H⁺ = C₃H₇NS

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	379.4 ± 2.1	kcal/mol	G+TS	Ingemann and Nibbering, 1985, 2	gas phase; value altered from reference due to change in acidity scale
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	372.3 ± 2.0	kcal/mol	IMRE	Ingemann and Nibbering, 1985, 2	gas phase; value altered from reference due to change in acidity scale

C₇H₆FO^- + Hydrogen cation =

By formula: C₇H₆FO^- + H⁺ = C₇H₇FO

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	379.7 ± 3.1	kcal/mol	G+TS	Ingemann and Nibbering, 1983	gas phase; value altered from reference due to change in acidity scale
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	372.0 ± 3.0	kcal/mol	IMRB	Ingemann and Nibbering, 1983	gas phase; value altered from reference due to change in acidity scale

C₂H₂F₃O^- + Hydrogen cation =

By formula: C₂H₂F₃O^- + H⁺ = C₂H₃F₃O

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	361.7 ± 2.5	kcal/mol	G+TS	Bartmess, Scott, et al., 1979	gas phase; value altered from reference due to change in acidity scale
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	354.1 ± 2.0	kcal/mol	IMRE	Bartmess, Scott, et al., 1979	gas phase; value altered from reference due to change in acidity scale

C₈H₇O₂^- + Hydrogen cation =

By formula: C₈H₇O₂^- + H⁺ = C₈H₈O₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	335.5 ± 2.1	kcal/mol	G+TS	Fujio, McIver, et al., 1981	gas phase; value altered from reference due to change in acidity scale
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	328.6 ± 2.0	kcal/mol	IMRE	Fujio, McIver, et al., 1981	gas phase; value altered from reference due to change in acidity scale

C₈H₁₀NO^- + Hydrogen cation =

By formula: C₈H₁₀NO^- + H⁺ = C₈H₁₁NO

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	350.3 ± 2.1	kcal/mol	G+TS	Fujio, McIver, et al., 1981	gas phase; value altered from reference due to change in acidity scale
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	343.5 ± 2.0	kcal/mol	IMRE	Fujio, McIver, et al., 1981	gas phase; value altered from reference due to change in acidity scale

C₁₀H₁₃O^- + Hydrogen cation =

By formula: C₁₀H₁₃O^- + H⁺ = C₁₀H₁₄O

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	348.5 ± 2.1	kcal/mol	G+TS	Fujio, McIver, et al., 1981	gas phase; value altered from reference due to change in acidity scale
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	341.6 ± 2.0	kcal/mol	IMRE	Fujio, McIver, et al., 1981	gas phase; value altered from reference due to change in acidity scale

C₈H₇O₃^- + Hydrogen cation =

By formula: C₈H₇O₃^- + H⁺ = C₈H₈O₃

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	337.1 ± 2.1	kcal/mol	G+TS	Fujio, McIver, et al., 1981	gas phase; value altered from reference due to change in acidity scale
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	330.3 ± 2.0	kcal/mol	IMRE	Fujio, McIver, et al., 1981	gas phase; value altered from reference due to change in acidity scale

C₇H₄F₃O^- + Hydrogen cation =

By formula: C₇H₄F₃O^- + H⁺ = C₇H₅F₃O

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	339.2 ± 2.1	kcal/mol	G+TS	Fujio, McIver, et al., 1981	gas phase; value altered from reference due to change in acidity scale
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	332.4 ± 2.0	kcal/mol	IMRE	Fujio, McIver, et al., 1981	gas phase; value altered from reference due to change in acidity scale

C₃H₇S^- + Hydrogen cation =

By formula: C₃H₇S^- + H⁺ = C₃H₈S

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	353.4 ± 2.2	kcal/mol	G+TS	Bartmess, Scott, et al., 1979	gas phase; value altered from reference due to change in acidity scale
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	347.1 ± 2.0	kcal/mol	IMRE	Bartmess, Scott, et al., 1979	gas phase; value altered from reference due to change in acidity scale

C₄H₉S^- + Hydrogen cation =

By formula: C₄H₉S^- + H⁺ = C₄H₁₀S

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	352.5 ± 2.2	kcal/mol	G+TS	Bartmess, Scott, et al., 1979	gas phase; value altered from reference due to change in acidity scale
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	346.2 ± 2.0	kcal/mol	IMRE	Bartmess, Scott, et al., 1979	gas phase; value altered from reference due to change in acidity scale

+ Hydrogen cation =

By formula: C₁₀H₉N₂^- + H⁺ = C₁₀H₁₀N₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	356.9 ± 2.1	kcal/mol	G+TS	Arnett, Venkatasubaramanian, et al., 1982	gas phase; value altered from reference due to change in acidity scale
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	349.6 ± 2.0	kcal/mol	IMRE	Arnett, Venkatasubaramanian, et al., 1982	gas phase; value altered from reference due to change in acidity scale

C₇H₅F₃N^- + Hydrogen cation =

By formula: C₇H₅F₃N^- + H⁺ = C₇H₆F₃N

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	356.9 ± 2.1	kcal/mol	G+TS	Bartmess, Scott, et al., 1979	gas phase; value altered from reference due to change in acidity scale
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	349.6 ± 2.0	kcal/mol	IMRE	Bartmess, Scott, et al., 1979	gas phase; value altered from reference due to change in acidity scale

C₄H₆N^- + Hydrogen cation =

By formula: C₄H₆N^- + H⁺ = C₄H₇N

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	375.1 ± 2.2	kcal/mol	G+TS	Bartmess, Scott, et al., 1979	gas phase; value altered from reference due to change in acidity scale
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	367.9 ± 2.0	kcal/mol	IMRE	Bartmess, Scott, et al., 1979	gas phase; value altered from reference due to change in acidity scale

C₉H₁₁^- + Hydrogen cation =

By formula: C₉H₁₁^- + H⁺ = C₉H₁₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	378.9 ± 2.1	kcal/mol	G+TS	Bartmess, Scott, et al., 1979	gas phase; value altered from reference due to change in acidity scale
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	372.9 ± 2.0	kcal/mol	IMRE	Bartmess, Scott, et al., 1979	gas phase; value altered from reference due to change in acidity scale

C₁₀H₁₂F₃O₂^- + Hydrogen cation = C₁₀H₁₃F₃O₂

By formula: C₁₀H₁₂F₃O₂^- + H⁺ = C₁₀H₁₃F₃O₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	337.7 ± 2.2	kcal/mol	G+TS	Taft and Topsom, 1987	gas phase; value altered from reference due to change in acidity scale
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	330.7 ± 2.0	kcal/mol	IMRE	Taft and Topsom, 1987	gas phase; value altered from reference due to change in acidity scale

C₉H₁₂FO₂^- + Hydrogen cation = C₉H₁₃FO₂

By formula: C₉H₁₂FO₂^- + H⁺ = C₉H₁₃FO₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	338.6 ± 2.2	kcal/mol	G+TS	Taft and Topsom, 1987	gas phase; value altered from reference due to change in acidity scale
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	331.6 ± 2.0	kcal/mol	IMRE	Taft and Topsom, 1987	gas phase; value altered from reference due to change in acidity scale

C₁₀H₁₂NO₂^- + Hydrogen cation = C₁₀H₁₃NO₂

By formula: C₁₀H₁₂NO₂^- + H⁺ = C₁₀H₁₃NO₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	335.6 ± 2.2	kcal/mol	G+TS	Taft and Topsom, 1987	gas phase; value altered from reference due to change in acidity scale
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	328.6 ± 2.0	kcal/mol	IMRE	Taft and Topsom, 1987	gas phase; value altered from reference due to change in acidity scale

C₁₀H₁₃O₂^- + Hydrogen cation = C₁₀H₁₄O₂

By formula: C₁₀H₁₃O₂^- + H⁺ = C₁₀H₁₄O₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	341.4 ± 2.2	kcal/mol	G+TS	Taft and Topsom, 1987	gas phase; value altered from reference due to change in acidity scale
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	334.4 ± 2.0	kcal/mol	IMRE	Taft and Topsom, 1987	gas phase; value altered from reference due to change in acidity scale

C₁₂H₁₅O₄^- + Hydrogen cation = C₁₂H₁₆O₄

By formula: C₁₂H₁₅O₄^- + H⁺ = C₁₂H₁₆O₄

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	338.9 ± 2.1	kcal/mol	G+TS	Taft and Topsom, 1987	gas phase; value altered from reference due to change in acidity scale
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	331.9 ± 2.0	kcal/mol	IMRE	Taft and Topsom, 1987	gas phase; value altered from reference due to change in acidity scale

C₉H₁₀ClO₂^- + Hydrogen cation = C₉H₁₁ClO₂

By formula: C₉H₁₀ClO₂^- + H⁺ = C₉H₁₁ClO₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	335.8 ± 2.2	kcal/mol	G+TS	Taft and Topsom, 1987	gas phase; value altered from reference due to change in acidity scale
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	328.8 ± 2.0	kcal/mol	IMRE	Taft and Topsom, 1987	gas phase; value altered from reference due to change in acidity scale

C₁₀H₁₀F₃O₂^- + Hydrogen cation = C₁₀H₁₁F₃O₂

By formula: C₁₀H₁₀F₃O₂^- + H⁺ = C₁₀H₁₁F₃O₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	335.8 ± 2.2	kcal/mol	G+TS	Taft and Topsom, 1987	gas phase; value altered from reference due to change in acidity scale
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	328.8 ± 2.0	kcal/mol	IMRE	Taft and Topsom, 1987	gas phase; value altered from reference due to change in acidity scale

C₅H₅O^- + Hydrogen cation =

By formula: C₅H₅O^- + H⁺ = C₅H₆O

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	383.8 ± 3.1	kcal/mol	G+TS	DePuy, Kass, et al., 1988	gas phase; Anion of 2-methylfuran. Order: H2O<furan<2-Me-furan<MeOH.
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	377.0 ± 3.0	kcal/mol	IMRB	DePuy, Kass, et al., 1988	gas phase; Anion of 2-methylfuran. Order: H2O<furan<2-Me-furan<MeOH.

C₄H₃F₆O^- + Hydrogen cation = C₄H₄F₆O

By formula: C₄H₃F₆O^- + H⁺ = C₄H₄F₆O

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	348.2 ± 2.1	kcal/mol	G+TS	Caldwell, McMahon, et al., 1985	gas phase; value altered from reference due to change in acidity scale
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	340.6 ± 2.0	kcal/mol	IMRE	Caldwell, McMahon, et al., 1985	gas phase; value altered from reference due to change in acidity scale

C₈H₆F₃^- + Hydrogen cation = C₈H₇F₃

By formula: C₈H₆F₃^- + H⁺ = C₈H₇F₃

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	367.0 ± 2.1	kcal/mol	G+TS	Caldwell and Bartmess	gas phase; value altered from reference due to change in acidity scale
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	359.8 ± 2.0	kcal/mol	IMRE	Caldwell and Bartmess	gas phase; value altered from reference due to change in acidity scale

C₅H₆NO^- + Hydrogen cation = C₅H₇NO

By formula: C₅H₆NO^- + H⁺ = C₅H₇NO

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	362.5 ± 2.1	kcal/mol	G+TS	Taft and Topsom, 1987	gas phase; value altered from reference due to change in acidity scale
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	354.8 ± 2.0	kcal/mol	IMRE	Taft and Topsom, 1987	gas phase; value altered from reference due to change in acidity scale

C₄H₃O^- + Hydrogen cation =

By formula: C₄H₃O^- + H⁺ = C₄H₄O

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	360.0 ± 2.3	kcal/mol	G+TS	Taft and Topsom, 1987	gas phase; value altered from reference due to change in acidity scale
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	352.3 ± 2.2	kcal/mol	IMRE	Taft and Topsom, 1987	gas phase; value altered from reference due to change in acidity scale

C₉H₁₂ClO₂^- + Hydrogen cation = C₉H₁₃ClO₂

By formula: C₉H₁₂ClO₂^- + H⁺ = C₉H₁₃ClO₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	338.0 ± 2.2	kcal/mol	G+TS	Taft and Topsom, 1987	gas phase; value altered from reference due to change in acidity scale
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	331.0 ± 2.0	kcal/mol	IMRE	Taft and Topsom, 1987	gas phase; value altered from reference due to change in acidity scale

C₉H₁₁O₂^- + Hydrogen cation =

By formula: C₉H₁₁O₂^- + H⁺ = C₉H₁₂O₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	342.3 ± 2.2	kcal/mol	G+TS	Taft and Topsom, 1987	gas phase; value altered from reference due to change in acidity scale
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	335.3 ± 2.0	kcal/mol	IMRE	Taft and Topsom, 1987	gas phase; value altered from reference due to change in acidity scale

H₂NSi^- + Hydrogen cation = H₃NSi

By formula: H₂NSi^- + H⁺ = H₃NSi

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	359.4 ± 3.2	kcal/mol	G+TS	Damrauer, Krempp, et al., 1993	gas phase; Between CF3CH2OH, pyrrole. Acid calculated to be HSiNH2
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	352.0 ± 3.0	kcal/mol	IMRB	Damrauer, Krempp, et al., 1993	gas phase; Between CF3CH2OH, pyrrole. Acid calculated to be HSiNH2

C₃H₄F₃O^- + Hydrogen cation =

By formula: C₃H₄F₃O^- + H⁺ = C₃H₅F₃O

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	360.3 ± 2.1	kcal/mol	G+TS	Caldwell, McMahon, et al., 1985	gas phase; value altered from reference due to change in acidity scale
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	353.7 ± 2.0	kcal/mol	IMRE	Caldwell, McMahon, et al., 1985	gas phase; value altered from reference due to change in acidity scale

C₄H₆F₃O^- + Hydrogen cation =

By formula: C₄H₆F₃O^- + H⁺ = C₄H₇F₃O

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	360.1 ± 2.1	kcal/mol	G+TS	Caldwell, McMahon, et al., 1985	gas phase; value altered from reference due to change in acidity scale
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	353.5 ± 2.0	kcal/mol	IMRE	Caldwell, McMahon, et al., 1985	gas phase; value altered from reference due to change in acidity scale

C₆H₇O₄^- + Hydrogen cation =

By formula: C₆H₇O₄^- + H⁺ = C₆H₈O₄

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	331.9 ± 2.1	kcal/mol	G+TS	Mishima, Matsuoka, et al., 2004	gas phase; Meldrums acid. Calc: keto form of acid more stable.
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	324.9 ± 2.0	kcal/mol	IMRE	Mishima, Matsuoka, et al., 2004	gas phase; Meldrums acid. Calc: keto form of acid more stable.

C₃H₄FO^- + Hydrogen cation =

By formula: C₃H₄FO^- + H⁺ = C₃H₅FO

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	366.1 ± 4.1	kcal/mol	G+TS	Clair and McMahon, 1980	gas phase; value altered from reference due to change in acidity scale
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	359.3 ± 4.0	kcal/mol	IMRB	Clair and McMahon, 1980	gas phase; value altered from reference due to change in acidity scale

C₈H₉^- + Hydrogen cation =

By formula: C₈H₉^- + H⁺ = C₈H₁₀

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	381.0 ± 2.6	kcal/mol	G+TS	Caldwell and Bartmess	gas phase; value altered from reference due to change in acidity scale
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	373.9 ± 2.5	kcal/mol	IMRE	Caldwell and Bartmess	gas phase; value altered from reference due to change in acidity scale

C₇H₆F^- + Hydrogen cation =

By formula: C₇H₆F^- + H⁺ = C₇H₇F

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	375.3 ± 2.1	kcal/mol	G+TS	Caldwell and Bartmess	gas phase; value altered from reference due to change in acidity scale
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	368.2 ± 2.0	kcal/mol	IMRE	Caldwell and Bartmess	gas phase; value altered from reference due to change in acidity scale

C₇H₆F^- + Hydrogen cation =

By formula: C₇H₆F^- + H⁺ = C₇H₇F

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	379.5 ± 2.1	kcal/mol	G+TS	Caldwell and Bartmess	gas phase; value altered from reference due to change in acidity scale
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	372.4 ± 2.0	kcal/mol	IMRE	Caldwell and Bartmess	gas phase; value altered from reference due to change in acidity scale

C₈H₇O^- + Hydrogen cation =

By formula: C₈H₇O^- + H⁺ = C₈H₈O

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	371.3 ± 2.1	kcal/mol	G+TS	Caldwell and Bartmess	gas phase; value altered from reference due to change in acidity scale
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	364.2 ± 2.0	kcal/mol	IMRE	Caldwell and Bartmess	gas phase; value altered from reference due to change in acidity scale

References

Go To: Top, Reaction thermochemistry data, Notes

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]

Kahn, Hehre, et al., 1984
Kahn, S.D.; Hehre, W.J.; Bartmess, J.E.; Caldwell, G., Effect of Metal Complexation on the Gas-phase Acidities of Alkylbenzenes, Organomet., 1984, 3, 11, 1740, https://doi.org/10.1021/om00089a024 . [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]

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]

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]

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]

Ingemann and Nibbering, 1985, 2
Ingemann, S.; Nibbering, N.M.M., Gas phase chemistry of dipole stabilized carbanions derived from N,N-dimethylthioformamide and N,N-dimethylnitrosamine, Acta Chem. Scand., Ser. B, 1985, 39, 697. [all data]

Ingemann and Nibbering, 1983
Ingemann, S.; Nibbering, N.M.M., Gas phase reactions of anions with 2-,3-, and 4-fluoroanisole, J. Org. Chem., 1983, 48, 183. [all data]

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]

Arnett, Venkatasubaramanian, et al., 1982
Arnett, E.M.; Venkatasubaramanian, K.G.; McIver, R.T.; Fukuda, E.K.; Bordwell, F.G.; Press, F.D., Stabilization of the monoanion of 1,8-diaminonaphthalene by intramolecular hydrogen bonding. A novel case of anion homoconjugation in superbase solution, J. Am. Chem. Soc., 1982, 104, 325. [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]

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]

Caldwell, McMahon, et al., 1985
Caldwell, G.; McMahon, T.B.; Kebarle, P.; Bartmess, J.E.; Kiplinger, J.P., Methyl substituent effects in the gas phase acidities of halosubstituted oxygen acids. A realignment with substituent effects in solution, J. Am. Chem. Soc., 1985, 107, 80. [all data]

Caldwell and Bartmess
Caldwell, G.; Bartmess, J.E., , Unpublished results. [all data]

Damrauer, Krempp, et al., 1993
Damrauer, R.; Krempp, M.; Ohair, R.A.J., Gas-Phase Chemistry of HSiS- and HSiNH- - Ions Related to Silathioformaldehyde and the Silaazomethine of Formaldehyde, J. Am. Chem. Soc., 1993, 115, 5, 1998, https://doi.org/10.1021/ja00058a055 . [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]

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]

Notes

Go To: Top, Reaction thermochemistry data, References

Symbols used in this document:

Δ_rG° Free energy of reaction at standard conditions

Δ_rH° Enthalpy of reaction at standard conditions
Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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Δ_rG°	Free energy of reaction at standard conditions
Δ_rH°	Enthalpy of reaction at standard conditions