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Benzonitrile, 4-hydroxy-


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

Quantity Value Units Method Reference Comment
Deltafsolid-14.56kcal/molCcbZavoianu, Ciocazanu, et al., 1988 
Quantity Value Units Method Reference Comment
Deltacsolid-814.6kcal/molCcbZavoianu, Ciocazanu, et al., 1988 

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

Chlorine anion + Benzonitrile, 4-hydroxy- = (Chlorine anion bullet Benzonitrile, 4-hydroxy-)

By formula: Cl- + C7H5NO = (Cl- bullet C7H5NO)

Quantity Value Units Method Reference Comment
Deltar35.1 ± 2.0kcal/molTDEqCummings, French, et al., 1977gas phase; Re-anchored to data in French, Ikuta, et al., 1982.; B,M,M
Deltar35.3kcal/molPHPMSPaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar25.cal/mol*KN/APaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M
Deltar28.cal/mol*KN/ACummings, French, et al., 1977gas phase; switching reaction(Cl-)4-Cl-phenol, Entropy change calculated or estimated; French, Ikuta, et al., 1982; M
Deltar26.cal/mol*KN/ACummings, French, et al., 1977gas phase; switching reaction(Cl-)4-F-phenol, Entropy change calculated or estimated; French, Ikuta, et al., 1982; M
Quantity Value Units Method Reference Comment
Deltar27.3 ± 2.0kcal/molTDEqCummings, French, et al., 1977gas phase; Re-anchored to data in French, Ikuta, et al., 1982.; B

Free energy of reaction

DeltarG° (kcal/mol) T (K) Method Reference Comment
24.7423.PHPMSPaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M
26.2300.PHPMSCummings, French, et al., 1977gas phase; switching reaction(Cl-)4-Cl-phenol, Entropy change calculated or estimated; French, Ikuta, et al., 1982; M
25.8300.PHPMSCummings, French, et al., 1977gas phase; switching reaction(Cl-)4-F-phenol, Entropy change calculated or estimated; French, Ikuta, et al., 1982; M

Bromine anion + Benzonitrile, 4-hydroxy- = (Bromine anion bullet Benzonitrile, 4-hydroxy-)

By formula: Br- + C7H5NO = (Br- bullet C7H5NO)

Quantity Value Units Method Reference Comment
Deltar27.8 ± 1.8kcal/molIMREPaul and Kebarle, 1990gas phase; «DELTA»Gaff at 423 K; B,M
Quantity Value Units Method Reference Comment
Deltar23.cal/mol*KN/APaul and Kebarle, 1990gas phase; switching reaction,Thermochemical ladder(Br-)C6H5OH, Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar18.1 ± 1.0kcal/molIMREPaul and Kebarle, 1990gas phase; «DELTA»Gaff at 423 K; B

Free energy of reaction

DeltarG° (kcal/mol) T (K) Method Reference Comment
18.1423.PHPMSPaul and Kebarle, 1990gas phase; switching reaction,Thermochemical ladder(Br-)C6H5OH, Entropy change calculated or estimated; M

Iodide + Benzonitrile, 4-hydroxy- = (Iodide bullet Benzonitrile, 4-hydroxy-)

By formula: I- + C7H5NO = (I- bullet C7H5NO)

Quantity Value Units Method Reference Comment
Deltar23.8 ± 1.8kcal/molIMREPaul and Kebarle, 1990gas phase; «DELTA»Gaff at 423 K; B,M
Quantity Value Units Method Reference Comment
Deltar21.cal/mol*KN/APaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar14.9 ± 1.0kcal/molIMREPaul and Kebarle, 1990gas phase; «DELTA»Gaff at 423 K; B

Free energy of reaction

DeltarG° (kcal/mol) T (K) Method Reference Comment
14.9423.PHPMSPaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M

C7H4NO- + Hydrogen cation = Benzonitrile, 4-hydroxy-

By formula: C7H4NO- + H+ = C7H5NO

Quantity Value Units Method Reference Comment
Deltar332.1 ± 2.1kcal/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Deltar332.6 ± 2.6kcal/molG+TSKebarle and McMahon, 1977gas phase; B
Quantity Value Units Method Reference Comment
Deltar325.3 ± 2.0kcal/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Deltar325.7 ± 2.0kcal/molIMREKebarle and McMahon, 1977gas phase; B

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

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


Mass spectrum (electron ionization)

Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, IR Spectrum, 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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Additional Data

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Owner NIST Mass Spectrometry Data Center
Collection (C) 2014 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin Japan AIST/NIMC Database- Spectrum MS-NW-3215
NIST MS number 231389

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References

Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), 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]


Notes

Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), References