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Benzene, (bromomethyl)-

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Gas phase 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Deltafgas84. ± 4.kJ/molEqkBenson and Buss, 1957 

Condensed phase 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Deltafliquid22.kJ/molCmHolm, 1973Grignard Rx
Deltafliquid16. ± 2.kJ/molChydAshcroft, Carson, et al., 1963 
Deltafliquid30. ± 14.kJ/molCmFowell and Mortimer, 1961 

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:
MS - José A. Martinho Simões
B - John E. Bartmess
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

Benzene, (bromomethyl)- (l) + magnesium (cr) = C7H7BrMg (solution)

By formula: C7H7Br (l) + Mg (cr) = C7H7BrMg (solution)

Quantity Value Units Method Reference Comment
Deltar-275.7 ± 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

C7H6Br- + Hydrogen cation = Benzene, (bromomethyl)-

By formula: C7H6Br- + H+ = C7H7Br

Quantity Value Units Method Reference Comment
Deltar1557. ± 8.8kJ/molG+TSPoutsma, Nash, et al., 1997gas phase; acidity comparable to MeCN, between HF and tBuCH(Me)OH; B
Quantity Value Units Method Reference Comment
Deltar1527. ± 8.4kJ/molIMRBPoutsma, Nash, et al., 1997gas phase; acidity comparable to MeCN, between HF and tBuCH(Me)OH; B

Hydrogen bromide + Benzene, (bromomethyl)- = Toluene + Bromine

By formula: HBr + C7H7Br = C7H8 + Br2

Quantity Value Units Method Reference Comment
Deltar33.9 ± 4.2kJ/molEqkBenson and Buss, 1957gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = 33. ± 4. kJ/mol; ALS

Stannane, trimethyl(phenylmethyl)- (l) + Bromine (g) = Benzene, (bromomethyl)- (l) + C3H9BrSn (l)

By formula: C10H16Sn (l) + Br2 (g) = C7H7Br (l) + C3H9BrSn (l)

Quantity Value Units Method Reference Comment
Deltar-226.6 ± 0.9kJ/molRSCPedley and Skinner, 1959Please also see Pedley and Rylance, 1977 and Cox and Pilcher, 1970, 2.; MS

Benzene, (bromomethyl)- + Water = Hydrogen bromide + Benzyl alcohol

By formula: C7H7Br + H2O = HBr + C7H8O

Quantity Value Units Method Reference Comment
Deltar-7.9kJ/molCmGellner and Skinner, 1949liquid phase; Heat of hydrloysis; ALS

C12H7MnO5 (cr) + 1.5Bromine (g) = Benzene, (bromomethyl)- (g) + manganese dibromide (cr) + 5Carbon monoxide (g)

By formula: C12H7MnO5 (cr) + 1.5Br2 (g) = C7H7Br (g) + Br2Mn (cr) + 5CO (g)

Quantity Value Units Method Reference Comment
Deltar-194.5 ± 7.8kJ/molHAL-HFCConnor, Zafarani-Moattar, et al., 1982MS

Benzene, (bromomethyl)- + 0.5Hydrogen = Toluene + 0.5Bromine

By formula: C7H7Br + 0.5H2 = C7H8 + 0.5Br2

Quantity Value Units Method Reference Comment
Deltar-4. ± 2.kJ/molChydAshcroft, Carson, et al., 1963liquid phase; ALS

Benzene, (bromomethyl)- + C4H9Li = Benzene, pentyl- + Lithium bromide

By formula: C7H7Br + C4H9Li = C11H16 + BrLi

Quantity Value Units Method Reference Comment
Deltar-338. ± 11.kJ/molCmFowell and Mortimer, 1961liquid phase; ALS

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Benson and Buss, 1957
Benson, S.W.; Buss, J.H., The thermodynamics of bromination of toluene and the heat of formation of the benzyl radical, J. Phys. Chem., 1957, 61, 104-109. [all data]

Holm, 1973
Holm, T., Thermochemistry of Grignard reagents. Enthalpies of formation of alkylmagnesium bromides and of alkyl bromides, J. Organomet. Chem., 1973, 56, 87-93. [all data]

Ashcroft, Carson, et al., 1963
Ashcroft, S.J.; Carson, A.S.; Pedley, J.B., Thermochemistry of reductions caused by lithium aluminium hydride. Part 2.-The heats of formation of benzyl bromide, benzyl iodide and the benzyl radical, Trans. Faraday Soc., 1963, 59, 2713-2717. [all data]

Fowell and Mortimer, 1961
Fowell, P.A.; Mortimer, C.T., 735. Heats of formation and bond energies. Part V. n-Butyl-lithium, J. Chem. Soc., 1961, 3793-3796. [all data]

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

Poutsma, Nash, et al., 1997
Poutsma, J.C.; Nash, J.J.; Paulino, J.A.; Squires, R.R., Absolute Heats of Formation of Phenylcarbene and Vinylcarbene, J. Am. Chem. Soc., 1997, 119, 20, 4686, https://doi.org/10.1021/ja963918s . [all data]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]

Pedley and Skinner, 1959
Pedley, J.B.; Skinner, H.A., Thermochemistry of metallic alkyls. Part 9.?Heats of bromination of some organo-tin compounds, Trans. Faraday Soc., 1959, 55, 544, https://doi.org/10.1039/tf9595500544 . [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, 2
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds in Academic Press, New York, 1970. [all data]

Gellner and Skinner, 1949
Gellner, O.H.; Skinner, H.A., Dissociation energies of carbon-halogen bonds. The bond strengths allyl-X and benzyl-X, J. Chem. Soc., 1949, 1145-1148. [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]


Notes

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