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Benzene, (bromomethyl)-

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Gas phase ion energetics 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 evaluated as indicated in comments:
L - Sharon G. Lias

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

Quantity Value Units Method Reference Comment
IE (evaluated)8.99 ± 0.015eVN/AN/AL

Ionization energy determinations

IE (eV) Method Reference Comment
9.02 ± 0.02PITraeger and Kompe, 1990LL
8.99 ± 0.015PIPECOBaer, Morrow, et al., 1988LL
8.9EIYeo and Williams, 1970RDSH
9.1 ± 0.1EIGrutzmacher, 1970RDSH
9.10 ± 0.05EIPignataro, Foffani, et al., 1966RDSH
9.23PESchmidt and Schweig, 1973Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C7H7+9.27 ± 0.02BrPITraeger and Kompe, 1990LL
C7H7+9.79BrPIPECOBaer, Morrow, et al., 1988T = 0K; LL
C7H7+9.80BrPIPECOBaer, Morrow, et al., 1988T = 298K; LL
C7H7+9.1BrEIYeo and Williams, 1970RDSH

De-protonation reactions

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

References

Go To: Top, Gas phase ion energetics data, Notes

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

Traeger and Kompe, 1990
Traeger, J.C.; Kompe, B.M., Threshold C7H7 formation from the benzyl halides by photoionization mass spectrometry, Int. J. Mass Spectrom. Ion Processes, 1990, 101, 111. [all data]

Baer, Morrow, et al., 1988
Baer, T.; Morrow, J.C.; Shao, J.D.; Olesik, S., Gas-phase heats of formation of C7H7+ isomers: m-Tolyl, p-tolyl, and benzyl ions, J. Am. Chem. Soc., 1988, 110, 5633. [all data]

Yeo and Williams, 1970
Yeo, A.N.H.; Williams, D.H., Rearrangement in the molecular ions of halogenotoluenes prior to fragmentation in the mass spectrometer, Chem. Commun., 1970, 886. [all data]

Grutzmacher, 1970
Grutzmacher, H.-F., Zum Mechanismus massenspektrometrischer Fragmentierungsreaktionen-IV: zur Bildung von Phenonium-Ionen bei der Elektronenstoss-Fragmentierung von -Phenylathylbromiden, Org. Mass Spectrom., 1970, 3, 131. [all data]

Pignataro, Foffani, et al., 1966
Pignataro, S.; Foffani, A.; Innorta, G.; Distefano, G., Molecular structural effects on the ionization potentials for metasubstituted aromatic compounds and for compounds of the type X-CH2-R, Z. Physik. Chem. (Frankfurt), 1966, 49, 291. [all data]

Schmidt and Schweig, 1973
Schmidt, H.; Schweig, A., C-Hal hyperkonjugation, Tetrahedron Lett., 1973, 981. [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]


Notes

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