Benzonitrile, 2-hydroxy-

• Formula: C₇H₅NO
• Molecular weight: 119.1207
• IUPAC Standard InChI:
  

  InChI=1S/C7H5NO/c8-5-6-3-1-2-4-7(6)9/h1-4,9H Download the identifier in a file.

• IUPAC Standard InChIKey: CHZCERSEMVWNHL-UHFFFAOYSA-N
• CAS Registry Number: 611-20-1
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
  The 3d structure may be viewed using Java or Javascript.
• Other names: Salicylonitrile; o-Cyanophenol; o-Hydroxybenzonitrile; Benzonitrile, o-hydroxy-; Salicylnitrile; 2-Cyanophenol; 2-Hydroxybenzonitrile; NSC 53558
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• Information on this page:
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Phase change data
  • Reaction thermochemistry data
  • Ion clustering data
  • IR Spectrum
  • Mass spectrum (electron ionization)
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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 compiled by: John E. Bartmess

View reactions leading to C₇H₅NO⁺ (ion structure unspecified)

De-protonation reactions

C₇H₄NO^- +  =

By formula: C₇H₄NO^- + H⁺ = C₇H₅NO

Quantity	Value	Units	Method	Reference	Comment
rH°	1400. ± 9.2	kJ/mol	G+TS	Fujio, McIver, et al., 1981	gas phase; value altered from reference due to change in acidity scale
rH°	1400. ± 12.	kJ/mol	G+TS	Kebarle and McMahon, 1977	gas phase
Quantity	Value	Units	Method	Reference	Comment
rG°	1369. ± 8.4	kJ/mol	IMRE	Fujio, McIver, et al., 1981	gas phase; value altered from reference due to change in acidity scale
rG°	1369. ± 8.4	kJ/mol	IMRE	Kebarle and McMahon, 1977	gas phase

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.

Fujio, McIver, et al., 1981
Fujio, M.; McIver, R.T., Jr.; Taft, R.W., Effects on the acidities of phenols from specific substituent-solvent interactions. Inherent substituent parameters from gas phase acidities, J. Am. Chem. Soc., 1981, 103, 4017. [all data]

Kebarle and McMahon, 1977
Kebarle, P.; McMahon, T.B., Intrinsic Acidities of Substituted Phenols and Benzoic Acids Determined by Gas Phase Proton Transfer Equilibria, J. Am. Chem. Soc., 1977, 99, 7, 2222, https://doi.org/10.1021/ja00449a032 . [all data]

Notes

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

• Symbols used in this document:
  

  rG°	Free energy of reaction at standard conditions
  rH°	Enthalpy of reaction at standard conditions

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