Fluoromethyl radical

Formula: CH₂F
Molecular weight: 33.0250
IUPAC Standard InChI: InChI=1S/CH2F/c1-2/h1H2
IUPAC Standard InChIKey: VUWZPRWSIVNGKG-UHFFFAOYSA-N
CAS Registry Number: 3744-29-4
Chemical structure:
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Reaction thermochemistry data

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Data compiled by: José A. Martinho Simões

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Individual Reactions

C₆H₂FMnO₅ (g) = C₅MnO₅ (g) + Fluoromethyl radical (g)

By formula: C₆H₂FMnO₅ (g) = C₅MnO₅ (g) + CH₂F (g)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	33.2 ± 3.6	kcal/mol	PIMS	Martinho Simões and Beauchamp, 1990	The reaction enthalpy was derived from the appearance energy of Mn(CO)5(+), 212.2 ± 1.1 kcal/mol, using Mn(CO)5(CH2F) as the neutral precursor, together with the adiabatic ionization energy of Mn(CO)5 radical, 179. ± 3.3 kcal/mol Martinho Simões and Beauchamp, 1990

Gas phase ion energetics data

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Data compiled as indicated in comments:
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
B - John E. Bartmess

View reactions leading to CH₂F⁺ (ion structure unspecified)

Electron affinity determinations

EA (eV)	Method	Reference	Comment
0.25 ± 0.18	D-EA	Graul and Squires, 1990	B

Ionization energy determinations

IE (eV)	Method	Reference	Comment
9.04 ± 0.01	PE	Andrews, Dyke, et al., 1984	LBLHLM
8.90	PE	Aue and Bowers, 1979	LLK
9.16 ± 0.02	DER	Reinke, Kraessig, et al., 1973	LLK
8.90	EI	Lossing, 1972	LLK
9.35	EI	Lossing, Kebarle, et al., 1959	RDSH
9.22 ± 0.01	PE	Andrews, Dyke, et al., 1984	Vertical value; LBLHLM

Vibrational and/or electronic energy levels

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Data compiled by: Marilyn E. Jacox

State: 5p

Energy (cm^-1)	Med.	References


T_o = 67265 ± 10	gas	Hudgens, Dulcey, et al., 1987

State: 4p

Energy (cm^-1)	Med.	Transition	λ_min (nm)	λ_max (nm)	References


T_o = 63275 ± 10	gas	4p-X	147	158	Hudgens, Dulcey, et al., 1987

Vib. sym.	No.	Approximate type of mode	cm^-1	Med.	Method	References


a₁	2	CF stretch	1580 ± 20	gas	MPI	Hudgens, Dulcey, et al., 1987
	3	CH₂ scissor	1443 ± 20	gas	MPI	Hudgens, Dulcey, et al., 1987
b₁	4	OPLA	1259 ± 20	gas	MPI	Hudgens, Dulcey, et al., 1987

State: 3p

Energy (cm^-1)	Med.	Transition	λ_min (nm)	λ_max (nm)	References


T_o = 52863 ± 10	gas	3p-X	167	193	Hudgens, Dulcey, et al., 1987

Vib. sym.	No.	Approximate type of mode	cm^-1	Med.	Method	References


a₁	2	CF stretch	1575 ± 20	gas	MPI	Hudgens, Dulcey, et al., 1987
	3	CH₂ scissor	1420 ± 20	gas	MPI	Hudgens, Dulcey, et al., 1987
b₁	4	OPLA	1223 ± 20	gas	MPI	Hudgens, Dulcey, et al., 1987

State: X

Vib. sym.	No.	Approximate type of mode	cm^-1		Med.	Method	References


a₁	1	CH₂ s-stretch	3044.38		gas	IR	Whitney, Dong, et al., 2006
	3	CF stretch	1170.42		gas	DL	Yamada and Hirota, 1986
	3	CF stretch	1165.4		Ne	IR	Wu, Chen, et al., 2010
	3	CF stretch	1163	m	Ar	IR	Jacox and Milligan, 1969 Raymond and Andrews, 1971 Jacox, 1981
b₁	4	OPLA	300 ± 30		gas	MW	Endo, Yamada, et al., 1983
	4	OPLA	260 ± 30		gas	MPI	Hudgens, Dulcey, et al., 1987
b₂	5	CH₂ a-stretch	3183.86		gas	IR	Whitney, Dong, et al., 2006

Additional references: Jacox, 1994, page 149; Jacox, 2003, page 176; Fessenden and Schuler, 1965; Mucha, Jennings, et al., 1977; Nolte, Wagner, et al., 1999

Notes

Medium

Energy separation between the v = 0 levels of the excited and electronic ground states.

References

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Martinho Simões and Beauchamp, 1990
Martinho Simões, J.A.; Beauchamp, J.L., Chem. Rev., 1990, 90, 629. [all data]

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

Andrews, Dyke, et al., 1984
Andrews, L.; Dyke, J.M.; Jonathan, N.; Keddar, N.; Morris, A.; Ridha, A., A photoelectron spectroscopic study of the ground states of CH₂F⁺ and CD₂F⁺, J. Phys. Chem., 1984, 88, 2364. [all data]

Aue and Bowers, 1979
Aue, D.H.; Bowers, M.T., Chapter 9. Stabilities of positive ions from equilibrium gas phase basicity measurements in Ions Chemistry,, ed. M.T. Bowers, 1979. [all data]

Reinke, Kraessig, et al., 1973
Reinke, D.; Kraessig, R.; Baumgartel, H., Photoreactions of small organic molecules, Z. Naturforsch. A:, 1973, 28, 1021. [all data]

Lossing, 1972
Lossing, F.P., Free radicals by mass spectrometry. XLIV. Ionization potentials bond dissociation energies for chloro-and fluoromethyl radicals, Bull. Soc. Chim. Belg., 1972, 81, 125. [all data]

Lossing, Kebarle, et al., 1959
Lossing, F.P.; Kebarle, P.; DeSousa, J.B., Ionization potentials of alkyl and halogenated alkyl free radicals, 1959. [all data]

Hudgens, Dulcey, et al., 1987
Hudgens, J.W.; Dulcey, C.S.; Long, G.R.; Bogan, D.J., Multiphoton ionization spectra of radical products in the F(2P)+ketene system: Spectral assignments and formation reaction for CH2F, observation of CF and CH, J. Chem. Phys., 1987, 87, 8, 4546, https://doi.org/10.1063/1.452867 . [all data]

Whitney, Dong, et al., 2006
Whitney, E.S.; Dong, F.; Nesbitt, D.J., Jet-cooled infrared spectroscopy in slit supersonic discharges: Symmetric and antisymmetric CH[sub 2] stretching modes of fluoromethyl (CH[sub 2]F) radical, J. Chem. Phys., 2006, 125, 5, 054304, https://doi.org/10.1063/1.2208613 . [all data]

Yamada and Hirota, 1986
Yamada, C.; Hirota, E., Infrared diode laser spectroscopy of the ν3 band of the fluoromethyl radical, CH2F, J. Mol. Spectrosc., 1986, 116, 1, 101, https://doi.org/10.1016/0022-2852(86)90255-9 . [all data]

Wu, Chen, et al., 2010
Wu, Y.-J.; Chen, H.-F.; Chou, S.-L.; Lin, M.-Y.; Cheng, B.M., Vacuum-ultraviolet photolysis of H3CF in solid neon: Infrared spectra of HCF and CF+, Chem. Phys. Lett., 2010, 497, 1-3, 12, https://doi.org/10.1016/j.cplett.2010.07.087 . [all data]

Jacox and Milligan, 1969
Jacox, M.E.; Milligan, D.E., Matrix-Isolation Study of the Vacuum-Ultraviolet Photolysis of Methyl Fluoride. The Infrared Spectra of the Free Radicals CF, HCF, and H2CF, J. Chem. Phys., 1969, 50, 8, 3252, https://doi.org/10.1063/1.1671548 . [all data]

Raymond and Andrews, 1971
Raymond, J.I.; Andrews, L., Matrix reactions of fluorohalomethanes with alkali metals. Infrared spectrum and bonding in the monofluoromethyl radical, J. Phys. Chem., 1971, 75, 21, 3235, https://doi.org/10.1021/j100690a007 . [all data]

Jacox, 1981
Jacox, M.E., Hydrogen-atom abstraction by atomic fluorine. Vibrational spectrum of the F+CH3F reaction products trapped in solid argon, Chem. Phys., 1981, 59, 1-2, 199, https://doi.org/10.1016/0301-0104(81)80100-0 . [all data]

Endo, Yamada, et al., 1983
Endo, Y.; Yamada, C.; Saito, S.; Hirota, E., The microwave spectrum of the fluoromethyl radical, CH2F, J. Chem. Phys., 1983, 79, 4, 1605, https://doi.org/10.1063/1.446006 . [all data]

Jacox, 1994
Jacox, M.E., Vibrational and electronic energy levels of polyatomic transient molecules, American Chemical Society, Washington, DC, 1994, 464. [all data]

Jacox, 2003
Jacox, M.E., Vibrational and electronic energy levels of polyatomic transient molecules: supplement B, J. Phys. Chem. Ref. Data, 2003, 32, 1, 1-441, https://doi.org/10.1063/1.1497629 . [all data]

Fessenden and Schuler, 1965
Fessenden, R.W.; Schuler, R.H., ESR Spectra and Structure of the Fluorinated Methyl Radicals, J. Chem. Phys., 1965, 43, 8, 2704, https://doi.org/10.1063/1.1697199 . [all data]

Mucha, Jennings, et al., 1977
Mucha, J.A.; Jennings, D.A.; Evenson, K.M.; Hougen, J.T., Far-infrared laser magnetic resonance spectrum of CH2F, J. Mol. Spectrosc., 1977, 68, 1, 122, https://doi.org/10.1016/0022-2852(77)90427-1 . [all data]

Nolte, Wagner, et al., 1999
Nolte, J.; Wagner, H.G.; Sears, T.J.; Temps, F., The Far-Infrared Laser Magnetic Resonance Spectrum of CH2F, J. Mol. Spectrosc., 1999, 195, 1, 43, https://doi.org/10.1006/jmsp.1999.7813 . [all data]

Notes

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Symbols used in this document:

EA Electron affinity

Δ_rH° Enthalpy of reaction at standard conditions
Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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EA	Electron affinity
Δ_rH°	Enthalpy of reaction at standard conditions