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
Δfsolid-60.92kJ/molCcbZavoianu, Ciocazanu, et al., 1988 
Quantity Value Units Method Reference Comment
Δcsolid-3408.kJ/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 • Benzonitrile, 4-hydroxy-)

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

Quantity Value Units Method Reference Comment
Δr147. ± 8.4kJ/molTDEqCummings, French, et al., 1977gas phase; Re-anchored to data in French, Ikuta, et al., 1982.; B,M,M
Δr148.kJ/molPHPMSPaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Δr100.J/mol*KN/APaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M
Δr120.J/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
Δr110.J/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
Δr114. ± 8.4kJ/molTDEqCummings, French, et al., 1977gas phase; Re-anchored to data in French, Ikuta, et al., 1982.; B

Free energy of reaction

ΔrG° (kJ/mol) T (K) Method Reference Comment
103.423.PHPMSPaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M
110.300.PHPMSCummings, French, et al., 1977gas phase; switching reaction(Cl-)4-Cl-phenol, Entropy change calculated or estimated; French, Ikuta, et al., 1982; M
108.300.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 • Benzonitrile, 4-hydroxy-)

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

Quantity Value Units Method Reference Comment
Δr116. ± 7.5kJ/molIMREPaul and Kebarle, 1990gas phase; ΔGaff at 423 K; B,M
Quantity Value Units Method Reference Comment
Δr96.J/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
Δr75.7 ± 4.2kJ/molIMREPaul and Kebarle, 1990gas phase; ΔGaff at 423 K; B

Free energy of reaction

ΔrG° (kJ/mol) T (K) Method Reference Comment
75.7423.PHPMSPaul and Kebarle, 1990gas phase; switching reaction,Thermochemical ladder(Br-)C6H5OH, Entropy change calculated or estimated; M

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

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

Quantity Value Units Method Reference Comment
Δr99.6 ± 7.5kJ/molIMREPaul and Kebarle, 1990gas phase; ΔGaff at 423 K; B,M
Quantity Value Units Method Reference Comment
Δr88.J/mol*KN/APaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Δr62.3 ± 4.2kJ/molIMREPaul and Kebarle, 1990gas phase; ΔGaff at 423 K; B

Free energy of reaction

ΔrG° (kJ/mol) T (K) Method Reference Comment
62.3423.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
Δr1390. ± 8.8kJ/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Δr1392. ± 11.kJ/molG+TSKebarle and McMahon, 1977gas phase; B
Quantity Value Units Method Reference Comment
Δr1361. ± 8.4kJ/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Δr1363. ± 8.4kJ/molIMREKebarle and McMahon, 1977gas phase; B

Gas phase ion energetics data

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

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

IE (eV) Method Reference Comment
9.40 ± 0.05EIBuchs, 1970RDSH

De-protonation reactions

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

By formula: C7H4NO- + H+ = C7H5NO

Quantity Value Units Method Reference Comment
Δr1390. ± 8.8kJ/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Δr1392. ± 11.kJ/molG+TSKebarle and McMahon, 1977gas phase; B
Quantity Value Units Method Reference Comment
Δr1361. ± 8.4kJ/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Δr1363. ± 8.4kJ/molIMREKebarle and McMahon, 1977gas phase; B

Ion clustering data

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

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

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

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

Quantity Value Units Method Reference Comment
Δr116. ± 7.5kJ/molIMREPaul and Kebarle, 1990gas phase; ΔGaff at 423 K; B,M
Quantity Value Units Method Reference Comment
Δr96.J/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
Δr75.7 ± 4.2kJ/molIMREPaul and Kebarle, 1990gas phase; ΔGaff at 423 K; B

Free energy of reaction

ΔrG° (kJ/mol) T (K) Method Reference Comment
75.7423.PHPMSPaul and Kebarle, 1990gas phase; switching reaction,Thermochemical ladder(Br-)C6H5OH, Entropy change calculated or estimated; M

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

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

Quantity Value Units Method Reference Comment
Δr147. ± 8.4kJ/molTDEqCummings, French, et al., 1977gas phase; Re-anchored to data in French, Ikuta, et al., 1982.; B,M,M
Δr148.kJ/molPHPMSPaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Δr100.J/mol*KN/APaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M
Δr120.J/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
Δr110.J/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
Δr114. ± 8.4kJ/molTDEqCummings, French, et al., 1977gas phase; Re-anchored to data in French, Ikuta, et al., 1982.; B

Free energy of reaction

ΔrG° (kJ/mol) T (K) Method Reference Comment
103.423.PHPMSPaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M
110.300.PHPMSCummings, French, et al., 1977gas phase; switching reaction(Cl-)4-Cl-phenol, Entropy change calculated or estimated; French, Ikuta, et al., 1982; M
108.300.PHPMSCummings, French, et al., 1977gas phase; switching reaction(Cl-)4-F-phenol, Entropy change calculated or estimated; French, Ikuta, et al., 1982; M

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

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

Quantity Value Units Method Reference Comment
Δr99.6 ± 7.5kJ/molIMREPaul and Kebarle, 1990gas phase; ΔGaff at 423 K; B,M
Quantity Value Units Method Reference Comment
Δr88.J/mol*KN/APaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Δr62.3 ± 4.2kJ/molIMREPaul and Kebarle, 1990gas phase; ΔGaff at 423 K; B

Free energy of reaction

ΔrG° (kJ/mol) T (K) Method Reference Comment
62.3423.PHPMSPaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M

IR Spectrum

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

Data compiled by: Coblentz Society, Inc.

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


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

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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, 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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