Benzyne

• Formula: C₆H₄
• Molecular weight: 76.0960
• IUPAC Standard InChI: InChI=1S/C6H4/c1-2-4-6-5-3-1/h1-4H Copy

  
• IUPAC Standard InChIKey: KLYCPFXDDDMZNQ-UHFFFAOYSA-N Copy
• CAS Registry Number: 462-80-6
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
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• Information on this page:
  • Reaction thermochemistry data
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Gas phase ion energetics data
  • Vibrational and/or electronic energy levels
• Data at other public NIST sites:
  • Microwave spectra (on physics lab web site)
  • Gas Phase Kinetics Database
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Reaction thermochemistry data

Go To: Top, References, Notes

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

 +  =

By formula: C₆H₃^- + H⁺ = C₆H₄

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

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

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

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

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.

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
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

Go To: Top, Reaction thermochemistry data, References

• Symbols used in this document:
  

  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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