Benzonitrile, 4-hydroxy-

• Formula: C₇H₅NO
• Molecular weight: 119.1207
• IUPAC Standard InChI: InChI=1S/C7H5NO/c8-5-6-1-3-7(9)4-2-6/h1-4,9H Copy

  
• IUPAC Standard InChIKey: CVNOWLNNPYYEOH-UHFFFAOYSA-N Copy
• CAS Registry Number: 767-00-0
• 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: Benzonitrile, p-hydroxy-; p-Cyanophenol; p-Hydroxybenzonitrile; 4-Cyanophenol; 4-Hydroxybenzonitrile; 4-Hydroxybenzoic acid nitrile
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Condensed phase thermochemistry data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • Ion clustering data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • References
  • Notes
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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

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:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias

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: Cl^- + C₇H₅NO = (Cl^- • C₇H₅NO)

Free energy of reaction

 +  = ( • )

By formula: Br^- + C₇H₅NO = (Br^- • C₇H₅NO)

Free energy of reaction

 +  = ( • )

By formula: I^- + C₇H₅NO = (I^- • C₇H₅NO)

Free energy of reaction

C₇H₄NO^- +  =

By formula: C₇H₄NO^- + H⁺ = C₇H₅NO

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 as indicated in comments:
B - John E. Bartmess
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

View reactions leading to C₇H₅NO⁺ (ion structure unspecified)

Ionization energy determinations

De-protonation reactions

C₇H₄NO^- +  =

By formula: C₇H₄NO^- + H⁺ = C₇H₅NO

Ion clustering 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:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. Searches may be limited to ion clustering reactions. A general reaction search form is also available.

Clustering reactions

 +  = ( • )

By formula: Br^- + C₇H₅NO = (Br^- • C₇H₅NO)

Free energy of reaction

 +  = ( • )

By formula: Cl^- + C₇H₅NO = (Cl^- • C₇H₅NO)

Free energy of reaction

 +  = ( • )

By formula: I^- + C₇H₅NO = (I^- • C₇H₅NO)

Free energy of reaction

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

• SOLUTION (ETHYL ETHER); Not specified, most likely a prism, grating, or hybrid spectrometer.; DIGITIZED BY NIST FROM HARD COPY; 4 cm^-1 resolution

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

• gas

Mass spectrum (electron ionization)

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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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Additional Data

References

Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), NIST Free Links, Notes

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

Zavoianu, Ciocazanu, et al., 1988
Zavoianu, D.; Ciocazanu, I.; Moga-Gheorghe, S.; Bornaz, C., Structure and reactivity of nitriles. Heat of combustion and formation of some benzonitrile derivatives, Rev. Chim. (Bucharest), 1988, 39, 487-489. [all data]

Cummings, French, et al., 1977
Cummings, J.B.; French, M.A.; Kebarle, P., Effect of charge delocalization on hydrogen bonding to negative ions and solvation of negative ions. Substituted phenols and phenoxide ions, J. Am. Chem. Soc., 1977, 99, 6999. [all data]

French, Ikuta, et al., 1982
French, M.A.; Ikuta, S.; Kebarle, P., Hydrogen bonding of O-H and C-H hydrogen donors to Cl^-. Results from mass spectrometric measurement of the ion-molecule equilibria RH + Cl^- = RHCl^-, Can. J. Chem., 1982, 60, 1907. [all data]

Paul and Kebarle, 1990
Paul, G.J.C.; Kebarle, P., Stabilities in the Gas Phase of the Hydrogen Bonded Complexes, YC6H4OH-X-, of Substituted Phenols, YC6H4OH, with the Halide Anions X-(Cl-, Br-), Can. J. Chem., 1990, 68, 11, 2070, https://doi.org/10.1139/v90-316 . [all data]

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]

Buchs, 1970
Buchs, A., Etude par spectrometrie de masse de l'ionisation de benzonitriles, de phenylacetonitriles et de N,N-dimethylanilines substitues, Helv. Chim. Acta, 1970, 53, 2026. [all data]

Notes

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• Symbols used in this document:
  

  T	Temperature
  ΔcH°solid	Enthalpy of combustion of solid at standard conditions
  ΔfH°solid	Enthalpy of formation of solid at standard conditions
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔrS°	Entropy of reaction at standard conditions

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