oF-phenide anion

Formula: C₆H₄F^-
Molecular weight: 95.0949
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Other data available:
- Gas phase ion energetics data
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Reaction thermochemistry data

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Individual Reactions

C₆H₄F^- + =

By formula: C₆H₄F^- + H⁺ = C₆H₅F

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	386.8 ± 2.1	kcal/mol	G+TS	Buker, Nibbering, et al., 1997	gas phase
Δ_rH°	387.3 ± 2.1	kcal/mol	G+TS	Andrade and Riveros, 1996	gas phase
Δ_rH°	387.2 ± 2.5	kcal/mol	TDEq	Meot-ner and Kafafi, 1988	gas phase; anchored to 88MEO scale, not the "87 acidity scale". The Kiefer, Zhang, et al., 1997 BDE is for ortho.
Δ_rH°	387.2 ± 2.5	kcal/mol	Bran	Wenthold and Squires, 1995	gas phase; By HO- cleavage of substituted silanes
Δ_rH°	387.2 ± 5.4	kcal/mol	G+TS	Briscese and Riveros, 1975	gas phase
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	378.6 ± 2.0	kcal/mol	IMRE	Buker, Nibbering, et al., 1997	gas phase
Δ_rG°	379.1 ± 2.0	kcal/mol	IMRE	Andrade and Riveros, 1996	gas phase
Δ_rG°	378.9 ± 2.0	kcal/mol	TDEq	Meot-ner and Kafafi, 1988	gas phase; anchored to 88MEO scale, not the "87 acidity scale". The Kiefer, Zhang, et al., 1997 BDE is for ortho.
Δ_rG°	379.0 ± 2.6	kcal/mol	H-TS	Wenthold and Squires, 1995	gas phase; By HO- cleavage of substituted silanes
Δ_rG°	379.0 ± 5.3	kcal/mol	IMRB	Briscese and Riveros, 1975	gas phase

References

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Buker, Nibbering, et al., 1997
Buker, H.H.; Nibbering, N.M.M.; Espinosa, D.; Mongin, F.; Schlosser, M., Additivity of substituent effects in the fluoroarene series: Equilibrium acidity in the gas phase and deprotonation rates in ethereal solution, Tetrahed. Lett., 1997, 38, 49, 8519-8522, https://doi.org/10.1016/S0040-4039(97)10303-3 . [all data]

Andrade and Riveros, 1996
Andrade, P.B.M.; Riveros, J.M., Relative Gas-phase Acidities of Fluoro- and Chlorobenzene, J. Mass Spectrom., 1996, 31, 7, 767, https://doi.org/10.1002/(SICI)1096-9888(199607)31:7<767::AID-JMS345>3.0.CO;2-Q . [all data]

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

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

Wenthold and Squires, 1995
Wenthold, P.G.; Squires, R.R., Determination of the gas-phase acidities of halogen-substituted aromatic compounds using the silane-cleavage method, J. Mass Spectrom., 1995, 30, 1, 17, https://doi.org/10.1002/jms.1190300105 . [all data]

Briscese and Riveros, 1975
Briscese, S.M.J.; Riveros, J.M., Gas phase nucleophilic reactions of aromatic systems, J. Am. Chem. Soc., 1975, 97, 230. [all data]

Notes

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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