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Methane, bromo-

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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 as indicated in comments:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
MS - José A. Martinho Simões
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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.

Individual Reactions

CH2Br- + Hydrogen cation = Methane, bromo-

By formula: CH2Br- + H+ = CH3Br

Quantity Value Units Method Reference Comment
Deltar1660. ± 10.kJ/molEndoHierl, Henchman, et al., 1992gas phase; HO- + MeBr:6.0±2.3 kcal/mol endo. "Better than Ingemann and Nibbering, 19852" 2.0 kcal would not show barrier; B
Deltar1650. ± 19.kJ/molEIAERogers, Simpson, et al., 2010gas phase; B
Deltar1643. ± 13.kJ/molG+TSIngemann and Nibbering, 1985, 2gas phase; B
Quantity Value Units Method Reference Comment
Deltar1631. ± 14.kJ/molH-TSHierl, Henchman, et al., 1992gas phase; HO- + MeBr:6.0±2.3 kcal/mol endo. "Better than Ingemann and Nibbering, 19852" 2.0 kcal would not show barrier; B
Deltar1614. ± 13.kJ/molIMRBIngemann and Nibbering, 1985, 2gas phase; B

Chlorine anion + Methane, bromo- = (Chlorine anion bullet Methane, bromo-)

By formula: Cl- + CH3Br = (Cl- bullet CH3Br)

Quantity Value Units Method Reference Comment
Deltar52.3 ± 4.2kJ/molTDAsLi, Ross, et al., 1996gas phase; B
Deltar45.6 ± 2.1kJ/molTDAsDougherty and Roberts, 1974gas phase; B,M
Deltar51. ± 13.kJ/molIMRBRiveros, Breda, et al., 1973gas phase; Anchored: Larson and McMahon, 1984; B
Quantity Value Units Method Reference Comment
Deltar53.6J/mol*KHPMSDougherty and Roberts, 1974gas phase; Entropy change is questionable; M
Quantity Value Units Method Reference Comment
Deltar28.5 ± 0.84kJ/molTDAsLi, Ross, et al., 1996gas phase; B
Deltar30. ± 5.0kJ/molTDAsDougherty and Roberts, 1974gas phase; B

Bromine anion + Methane, bromo- = (Bromine anion bullet Methane, bromo-)

By formula: Br- + CH3Br = (Br- bullet CH3Br)

Quantity Value Units Method Reference Comment
Deltar46.9 ± 4.2kJ/molTDAsLi, Ross, et al., 1996gas phase; B
Deltar38.5 ± 2.1kJ/molTDAsDougherty and Roberts, 1974gas phase; B,M
Quantity Value Units Method Reference Comment
Deltar58.6J/mol*KHPMSDougherty and Roberts, 1974gas phase; M
Quantity Value Units Method Reference Comment
Deltar19.2 ± 0.84kJ/molTDAsLi, Ross, et al., 1996gas phase; B
Deltar20.9 ± 3.3kJ/molTDAsDougherty and Roberts, 1974gas phase; B

magnesium (cr) + Methane, bromo- (l) = CH3BrMg (solution)

By formula: Mg (cr) + CH3Br (l) = CH3BrMg (solution)

Quantity Value Units Method Reference Comment
Deltar-267.8 ± 4.4kJ/molRSCHolm, 1981solvent: Diethyl ether; Due to the possibility of side reactions, the enthalpy of reaction was not considered to be sufficiently reliable for deriving the enthalpy of formation of the Grignard reagent Holm, 1981; MS

Methyl cation + Methane, bromo- = (Methyl cation bullet Methane, bromo-)

By formula: CH3+ + CH3Br = (CH3+ bullet CH3Br)

Quantity Value Units Method Reference Comment
Deltar265.kJ/molPHPMSMcMahon, Heinis, et al., 1988gas phase; switching reaction(CH3+)N2, Entropy change calculated or estimated, uses MCA(N2) = 202. kJ/mol; Foster, Williamson, et al., 1974; M

Iodide + Methane, bromo- = (Iodide bullet Methane, bromo-)

By formula: I- + CH3Br = (I- bullet CH3Br)

Quantity Value Units Method Reference Comment
Deltar34.7 ± 0.84kJ/molN/AVan Duzor, Wei, et al., 2010gas phase; B
Deltar34.7 ± 2.1kJ/molPDisCyr, Bishea, et al., 1992gas phase; B

Trimethylindium (l) + 3Bromine (l) = Br3In (cr) + 3Methane, bromo- (g)

By formula: C3H9In (l) + 3Br2 (l) = Br3In (cr) + 3CH3Br (g)

Quantity Value Units Method Reference Comment
Deltar-665.3 ± 4.2kJ/molRSCClarke and Price, 1968Please also see Pedley and Rylance, 1977 and Cox and Pilcher, 1970.; MS

CH6N+ + Methane, bromo- = (CH6N+ bullet Methane, bromo-)

By formula: CH6N+ + CH3Br = (CH6N+ bullet CH3Br)

Quantity Value Units Method Reference Comment
Deltar46.9kJ/molPHPMSMeot-Ner, 1984gas phase; M
Quantity Value Units Method Reference Comment
Deltar87.9J/mol*KPHPMSMeot-Ner, 1984gas phase; M

Mercury, dimethyl- (l) + 2Bromine (l) = 2Methane, bromo- (g) + Mercury(II) bromide (cr)

By formula: C2H6Hg (l) + 2Br2 (l) = 2CH3Br (g) + Br2Hg (cr)

Quantity Value Units Method Reference Comment
Deltar-302.1 ± 2.5kJ/molRSCHartley, Pritchard, et al., 1950Please also see Pedley and Rylance, 1977 and Cox and Pilcher, 1970.; MS

Stannane, tetramethyl- (l) + Bromine (g) = C3H9BrSn (l) + Methane, bromo- (g)

By formula: C4H12Sn (l) + Br2 (g) = C3H9BrSn (l) + CH3Br (g)

Quantity Value Units Method Reference Comment
Deltar-202.1 ± 2.9kJ/molRSCPedley, Skinner, et al., 1957Please also see Pedley and Rylance, 1977 and Cox and Pilcher, 1970.; MS

Manganese, pentacarbonylmethyl- (cr) + 1.5Bromine (g) = manganese dibromide (cr) + 5Carbon monoxide (g) + Methane, bromo- (g)

By formula: C6H3MnO5 (cr) + 1.5Br2 (g) = Br2Mn (cr) + 5CO (g) + CH3Br (g)

Quantity Value Units Method Reference Comment
Deltar-209. ± 3.kJ/molHAL-HFCConnor, Zafarani-Moattar, et al., 1982MS

Manganese, acetylpentacarbonyl-, (OC-6-21)- (cr) + 1.5Bromine (g) = manganese dibromide (cr) + 6Carbon monoxide (g) + Methane, bromo- (g)

By formula: C7H3MnO6 (cr) + 1.5Br2 (g) = Br2Mn (cr) + 6CO (g) + CH3Br (g)

Quantity Value Units Method Reference Comment
Deltar-161. ± 5.kJ/molHAL-HFCConnor, Zafarani-Moattar, et al., 1982MS

Hydrogen + 2Methane, bromo- = 2Methane + Bromine

By formula: H2 + 2CH3Br = 2CH4 + Br2

Quantity Value Units Method Reference Comment
Deltar-28. ± 3.kJ/molChydAdams, Carson, et al., 1966liquid phase; ALS

Hydrogen + Methane, bromo- = Hydrogen bromide + Methane

By formula: H2 + CH3Br = HBr + CH4

Quantity Value Units Method Reference Comment
Deltar-73.6 ± 1.4kJ/molChydFowell, Lacher, et al., 1965gas phase; ALS

Methane + Bromine = Hydrogen bromide + Methane, bromo-

By formula: CH4 + Br2 = HBr + CH3Br

Quantity Value Units Method Reference Comment
Deltar-26.4 ± 0.7kJ/molEqkFerguson, Okafo, et al., 1973gas phase; ALS

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.

Hierl, Henchman, et al., 1992
Hierl, P.M.; Henchman, M.J.; Paulson, J.F., Threshold Energies for the Reactions HO- + MeX - MeOH + X- measured by Tandem Mass Spectrometry: Acidities of MeCl and MeBr, Int. J. Mass Spectrom. Ion Proc., 1992, 117, 475, https://doi.org/10.1016/0168-1176(92)80109-E . [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]

Rogers, Simpson, et al., 2010
Rogers, N.J.; Simpson, M.J.; Tuckett, R.P.; Dunn, K.F.; Latimer, C.J., Vacuum-UV negative photoion spectroscopy of CH3F, CH3Cl and CH3Br, Phys. Chem. Chem. Phys., 2010, 12, 36, 10971-10980, https://doi.org/10.1039/c0cp00234h . [all data]

Ingemann and Nibbering, 1985, 2
Ingemann, S.; Nibbering, N.M.M., Gas-phase acidity of CH3X [X = P(CH3)2, SCH3, F, Cl, Br, I] compounds, J. Chem. Soc. Perkin Trans. 2, 1985, 837. [all data]

Li, Ross, et al., 1996
Li, C.; Ross, P.; Szulejko, J.; McMahon, T.B., High-Pressure Mass Spectrometric Investigations of the Potential Energy Surfaces of Gas-Phase Sn2 Reactions., J. Am. Chem. Soc., 1996, 118, 39, 9360, https://doi.org/10.1021/ja960565o . [all data]

Dougherty and Roberts, 1974
Dougherty, R.C.; Roberts, J.D., SN2 reactions in the gas phase. Nucleophilicity effects, Org. Mass Spectrom., 1974, 8, 81. [all data]

Riveros, Breda, et al., 1973
Riveros, J.M.; Breda, A.C.; Blair, L.K., Formation and relative stability of chloride ion clusters in the gas phase by ICR spectroscopy, J. Am. Chem. Soc., 1973, 95, 4066. [all data]

Larson and McMahon, 1984
Larson, J.W.; McMahon, T.B., Fluoride and chloride affinities of main group oxides, fluorides, oxofluorides, and alkyls. Quantitative scales of lewis acidities from ion cyclotron resonance halide-exchange equilibria, J. Phys. Chem., 1984, 88, 1083. [all data]

Holm, 1981
Holm, T., J. Chem. Soc., Perkin Trans. II, 1981, 464.. [all data]

McMahon, Heinis, et al., 1988
McMahon, T.; Heinis, T.; Nicol, G.; Hovey, J.K.; Kebarle, P., Methyl Cation Affinities, J. Am. Chem. Soc., 1988, 110, 23, 7591, https://doi.org/10.1021/ja00231a002 . [all data]

Foster, Williamson, et al., 1974
Foster, M.S.; Williamson, A.D.; Beauchamp, J.L., Photoionization mass spectrometry of trans-azomethane, Int. J. Mass Spectrom. Ion Phys., 1974, 15, 429. [all data]

Van Duzor, Wei, et al., 2010
Van Duzor, M.; Wei, J.; Mbaiwa, F.; Mabbs, R., I-center dot CH3X (X=Cl, Br, I) photodetachment: The effect of electron-molecule interactions in cluster anion photodetachment spectra and angular distributions, J. Chem. Phys., 2010, 133, 14, 144303, https://doi.org/10.1063/1.3487739 . [all data]

Cyr, Bishea, et al., 1992
Cyr, D.M.; Bishea, G.A.; Scarton, M.G.; Johnson, M.A., Observation of Charge-Transfer Excited States in the I-.CH3I, I-.CH3Br, and I-.CH2Br2 S(N)2 Reaction Intermediates Using Photofragmentation, J. Chem. Phys., 1992, 97, 8, 5911, https://doi.org/10.1063/1.463752 . [all data]

Clarke and Price, 1968
Clarke, W.D.; Price, S.J.W., Can. J. Chem., 1968, 46, 1633. [all data]

Pedley and Rylance, 1977
Pedley, J.B.; Rylance, J., Computer Analysed Thermochemical Data: Organic and Organometallic Compounds, University of Sussex, Brigton, 1977. [all data]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds in Academic Press, New York, 1970. [all data]

Meot-Ner, 1984
Meot-Ner, (Mautner)M., The Ionic Hydrogen Bond and Ion Solvation. 1. -NH+ O-, -NH+ N- and -OH+ O- Bonds. Correlations with Proton Affinity. Deviations Due to Structural Effects, J. Am. Chem. Soc., 1984, 106, 5, 1257, https://doi.org/10.1021/ja00317a015 . [all data]

Hartley, Pritchard, et al., 1950
Hartley, K.; Pritchard, H.O.; Skinner, H.A., Thermochemistry of metallic alkyls. III.?mercury dimethyl and mercury methyl halides, Trans. Faraday Soc., 1950, 46, 1019, https://doi.org/10.1039/tf9504601019 . [all data]

Pedley, Skinner, et al., 1957
Pedley, J.B.; Skinner, H.A.; Chernick, C.L., Thermochemistry of metallic alkyls. Part 8.?Tin tetramethyl, and hexamethyl distannane, Trans. Faraday Soc., 1957, 53, 1612, https://doi.org/10.1039/tf9575301612 . [all data]

Connor, Zafarani-Moattar, et al., 1982
Connor, J.A.; Zafarani-Moattar, M.T.; Bickerton, J.; El-Saied, N.I.; Suradi, S.; Carson, R.; Al Takkhin, G.; Skinner, H.A., Organomet., 1982, 1, 1166. [all data]

Adams, Carson, et al., 1966
Adams, G.P.; Carson, A.S.; Laye, P.G., Thermochemistry of reductions caused by lithium aluminium hydride. Part 4.-Heat of formation of methyl bromide, Trans. Faraday Soc., 1966, 62, 1447-1449. [all data]

Fowell, Lacher, et al., 1965
Fowell, P.; Lacher, J.R.; Park, J.D., Reaction heats of organic compounds. Part 3.-Heats of hydrogenation of methyl bromide and ethyl bromide, Trans. Faraday Soc., 1965, 61, 1324-1327. [all data]

Ferguson, Okafo, et al., 1973
Ferguson, K.C.; Okafo, E.N.; Whittle, E., Bond dissociation energies from equilibrium studies Part 4.-The equilibrium Br2 + CH4 = HBr + CH3Br. Determination of D(CH3-Br) and «DELTA»Hf°(CH3Br,g), J. Chem. Soc. Faraday Trans. 1, 1973, 69, 295-301. [all data]


Notes

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