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Benzyne


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
Deltafgas105. ± 2.4kcal/molIonRiveros, Ingeman, et al., 1991Bracketing technique
Deltafgas106. ± 3.kcal/molIonWenthold, Paulino, et al., 1991collision-induced dissociation
Deltafgas118. ± 5.kcal/molIonPollack and Hehre, 1980 

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 by: John E. Bartmess

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

benzynide anion + Hydrogen cation = Benzyne

By formula: C6H3- + H+ = C6H4

Quantity Value Units Method Reference Comment
Deltar378.7 ± 3.1kcal/molG+TSGuo and Grabowski, 1991gas phase; Acidity between MeOH and tBuOH, comparable to EtOH
Quantity Value Units Method Reference Comment
Deltar371.0 ± 3.0kcal/molIMRBGuo and Grabowski, 1991gas phase; Acidity between MeOH and tBuOH, comparable to EtOH
Deltar372.0 ± 5.0kcal/molIMRBGronert and DePuy, 1989gas phase

(CAS Reg. No. 72863-53-7 bullet 4294967295Benzyne) + Benzyne = CAS Reg. No. 72863-53-7

By formula: (CAS Reg. No. 72863-53-7 bullet 4294967295C6H4) + C6H4 = CAS Reg. No. 72863-53-7

Quantity Value Units Method Reference Comment
Deltar19.5 ± 4.1kcal/molN/AAndrade and Riveros, 1996gas phase
Deltar16.7 ± 3.7kcal/molTherWenthold and Squires, 1995gas phase
Deltar15.7 ± 3.0kcal/molCIDTWenthold, Paulino, et al., 1991, 2gas phase; Between PhF, furan

(CAS Reg. No. 77748-26-6 bullet 4294967295Benzyne) + Benzyne = CAS Reg. No. 77748-26-6

By formula: (CAS Reg. No. 77748-26-6 bullet 4294967295C6H4) + C6H4 = CAS Reg. No. 77748-26-6

Quantity Value Units Method Reference Comment
Deltar54.1 ± 4.4kcal/molN/AMeot-ner and Kafafi, 1988gas phase; anchored to 88MEO scale, not the "87 acidity scale". The Kiefer, Zhang, et al., 1997 BDE is for ortho.

References

Go To: Top, Gas 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.

Riveros, Ingeman, et al., 1991
Riveros, J.M.; Ingeman, S.; Nibbering, N.M.M., Formation of gas-phase solvated Br-and I- ion/molecule reactions of halobenzenes. Revised heat of formation of benzyne, J. Am. Chem. Soc., 1991, 113, 1053. [all data]

Wenthold, Paulino, et al., 1991
Wenthold, P.G.; Paulino, J.A.; Squires, R.R., The absolute heats of formation of o-,m-, and p-benzyne, J. Am. Chem. Soc., 1991, 113, 7414-7415. [all data]

Pollack and Hehre, 1980
Pollack, S.K.; Hehre, W.J., Determination of the heat of formation of ortho-benzyne by ion cyclotron resonance spectroscopy, Tetrahedron Lett., 1980, 21, 2483-2486. [all data]

Guo and Grabowski, 1991
Guo, Y.L.; Grabowski, J.J., Reactions of the Benzyne Radical Anion in the Gas Phase, the Acidity of the Phenyl Radical, and the Heat of Formation of ortho-Benzyne, J. Am. Chem. Soc., 1991, 113, 16, 5923, https://doi.org/10.1021/ja00016a001 . [all data]

Gronert and DePuy, 1989
Gronert, S.; DePuy, C.H., The Dehydrophenyl Anion and the Gas Phase Ion Chemistry of Benzyne, J. Am. Chem. Soc., 1989, 111, 26, 9253, https://doi.org/10.1021/ja00208a032 . [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]

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]

Wenthold, Paulino, et al., 1991, 2
Wenthold, P.G.; Paulino, J.A.; Squires, R.R., The Absolute Heats of Formation of ortho-Benzyne, meta-Benzyne, and para-Benzyne, J. Am. Chem. Soc., 1991, 113, 19, 7414, https://doi.org/10.1021/ja00019a044 . [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]


Notes

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