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Phenol

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Ion clustering 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 as indicated in comments:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
RCD - Robert C. Dunbar

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 + Phenol = (Bromine anion bullet Phenol)

By formula: Br- + C6H6O = (Br- bullet C6H6O)

Quantity Value Units Method Reference Comment
Deltar87.0 ± 7.5kJ/molIMREPaul and Kebarle, 1990gas phase; «DELTA»Gaff at 423 K; B,M
Deltar82.0kJ/molPHPMSPaul and Kebarle, 1991gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar84.J/mol*KN/APaul and Kebarle, 1991gas phase; Entropy change calculated or estimated; M
Deltar96.J/mol*KN/APaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar46.4 ± 4.2kJ/molIMREPaul and Kebarle, 1990gas phase; «DELTA»Gaff at 423 K; B

Free energy of reaction

DeltarG° (kJ/mol) T (K) Method Reference Comment
46.4423.PHPMSPaul and Kebarle, 1991gas phase; Entropy change calculated or estimated; M
46.4423.PHPMSPaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M

MeCO2 anion + Phenol = (MeCO2 anion bullet Phenol)

By formula: C2H3O2- + C6H6O = (C2H3O2- bullet C6H6O)

Quantity Value Units Method Reference Comment
Deltar109. ± 4.2kJ/molN/AMeot-Ner and Sieck, 1986gas phase; B,M
Quantity Value Units Method Reference Comment
Deltar100.J/mol*KPHPMSMeot-Ner and Sieck, 1986gas phase; M
Quantity Value Units Method Reference Comment
Deltar79.1 ± 6.7kJ/molTDAsMeot-Ner and Sieck, 1986gas phase; B

Chlorine anion + Phenol = (Chlorine anion bullet Phenol)

By formula: Cl- + C6H6O = (Cl- bullet C6H6O)

Quantity Value Units Method Reference Comment
Deltar109. ± 8.4kJ/molTDAsFrench, Ikuta, et al., 1982gas phase; B,M
Deltar109. ± 8.4kJ/molTDEqCummings, French, et al., 1977gas phase; Re-anchored to data in French, Ikuta, et al., 1982.; B
Deltar115.kJ/molPHPMSKebarle, 1977gas phase; M
Deltar111.kJ/molPHPMSPaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M
Deltar81.2 ± 8.4kJ/molTDAsYamdagni and Kebarle, 1971gas phase; B,M
Quantity Value Units Method Reference Comment
Deltar109.J/mol*KPHPMSFrench, Ikuta, et al., 1982gas phase; M
Deltar100.J/mol*KPHPMSKebarle, 1977gas phase; M
Deltar100.J/mol*KN/APaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M
Deltar64.9J/mol*KPHPMSYamdagni and Kebarle, 1971gas phase; M
Quantity Value Units Method Reference Comment
Deltar80.3 ± 8.4kJ/molTDAsFrench, Ikuta, et al., 1982gas phase; B
Deltar77.4 ± 8.4kJ/molTDEqCummings, French, et al., 1977gas phase; Re-anchored to data in French, Ikuta, et al., 1982.; B
Deltar61.9 ± 8.4kJ/molTDAsYamdagni and Kebarle, 1971gas phase; B

Free energy of reaction

DeltarG° (kJ/mol) T (K) Method Reference Comment
66.5423.PHPMSPaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M

Cesium ion (1+) + Phenol = (Cesium ion (1+) bullet Phenol)

By formula: Cs+ + C6H6O = (Cs+ bullet C6H6O)

Quantity Value Units Method Reference Comment
Deltar66. ± 3.kJ/molCIDTAmunugama and Rodgers, 2002RCD

(Cesium ion (1+) bullet Phenol) + Phenol = (Cesium ion (1+) bullet 2Phenol)

By formula: (Cs+ bullet C6H6O) + C6H6O = (Cs+ bullet 2C6H6O)

Quantity Value Units Method Reference Comment
Deltar61. ± 3.kJ/molCIDTAmunugama and Rodgers, 2002RCD

Fluorine anion + Phenol = (Fluorine anion bullet Phenol)

By formula: F- + C6H6O = (F- bullet C6H6O)

Quantity Value Units Method Reference Comment
Deltar173. ± 8.4kJ/molIMRELarson and McMahon, 1983gas phase; These relative affinities are ca. 10 kcal/mol weaker than threshold values (see Wenthold and Squires, 1995) for donors greater than ca. 27 kcal/mol in free energy. This discrepancy has not yet been resolved, though the stronger value appears preferable.; B,M
Quantity Value Units Method Reference Comment
Deltar110.J/mol*KN/ALarson and McMahon, 1983gas phase; switching reaction(F-)H2O, Entropy change calculated or estimated; Arshadi, Yamdagni, et al., 1970; M
Quantity Value Units Method Reference Comment
Deltar140. ± 8.4kJ/molIMRELarson and McMahon, 1983gas phase; These relative affinities are ca. 10 kcal/mol weaker than threshold values (see Wenthold and Squires, 1995) for donors greater than ca. 27 kcal/mol in free energy. This discrepancy has not yet been resolved, though the stronger value appears preferable.; B,M

Iodide + Phenol = (Iodide bullet Phenol)

By formula: I- + C6H6O = (I- bullet C6H6O)

Quantity Value Units Method Reference Comment
Deltar72.4 ± 7.5kJ/molIMREPaul and Kebarle, 1990gas phase; «DELTA»Gaff at 423 K; B,M
Quantity Value Units Method Reference Comment
Deltar88.J/mol*KN/APaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar35. ± 4.2kJ/molIMREPaul and Kebarle, 1990gas phase; «DELTA»Gaff at 423 K; B

Free energy of reaction

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

Potassium ion (1+) + Phenol = (Potassium ion (1+) bullet Phenol)

By formula: K+ + C6H6O = (K+ bullet C6H6O)

Quantity Value Units Method Reference Comment
Deltar74. ± 3.kJ/molCIDTAmunugama and Rodgers, 2002RCD

(Potassium ion (1+) bullet Phenol) + Phenol = (Potassium ion (1+) bullet 2Phenol)

By formula: (K+ bullet C6H6O) + C6H6O = (K+ bullet 2C6H6O)

Quantity Value Units Method Reference Comment
Deltar68. ± 3.kJ/molCIDTAmunugama and Rodgers, 2002RCD

Lithium ion (1+) + Phenol = (Lithium ion (1+) bullet Phenol)

By formula: Li+ + C6H6O = (Li+ bullet C6H6O)

Quantity Value Units Method Reference Comment
Deltar178. ± 17.kJ/molCIDTAmunugama and Rodgers, 2002RCD

(Lithium ion (1+) bullet Phenol) + Phenol = (Lithium ion (1+) bullet 2Phenol)

By formula: (Li+ bullet C6H6O) + C6H6O = (Li+ bullet 2C6H6O)

Quantity Value Units Method Reference Comment
Deltar115. ± 3.kJ/molCIDTAmunugama and Rodgers, 2002RCD

Sodium ion (1+) + Phenol = (Sodium ion (1+) bullet Phenol)

By formula: Na+ + C6H6O = (Na+ bullet C6H6O)

Quantity Value Units Method Reference Comment
Deltar102. ± 3.kJ/molCIDTAmunugama and Rodgers, 2002RCD
Deltar98. ± 3.kJ/molCIDTArmentrout and Rodgers, 2000RCD

Free energy of reaction

DeltarG° (kJ/mol) T (K) Method Reference Comment
69.9298.IMREMcMahon and Ohanessian, 2000Anchor alanine=39.89; RCD

(Sodium ion (1+) bullet Phenol) + Phenol = (Sodium ion (1+) bullet 2Phenol)

By formula: (Na+ bullet C6H6O) + C6H6O = (Na+ bullet 2C6H6O)

Quantity Value Units Method Reference Comment
Deltar82. ± 3.kJ/molCIDTAmunugama and Rodgers, 2002RCD

Rubidium ion (1+) + Phenol = (Rubidium ion (1+) bullet Phenol)

By formula: Rb+ + C6H6O = (Rb+ bullet C6H6O)

Quantity Value Units Method Reference Comment
Deltar69. ± 3.kJ/molCIDTAmunugama and Rodgers, 2002RCD

(Rubidium ion (1+) bullet Phenol) + Phenol = (Rubidium ion (1+) bullet 2Phenol)

By formula: (Rb+ bullet C6H6O) + C6H6O = (Rb+ bullet 2C6H6O)

Quantity Value Units Method Reference Comment
Deltar64. ± 3.kJ/molCIDTAmunugama and Rodgers, 2002RCD

References

Go To: Top, Ion clustering data, Notes

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

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]

Paul and Kebarle, 1991
Paul, G.J.C.; Kebarle, P., Stabilities of Complexes of Br- with Substituted Benzenes (SB) Based on Determinations of the Gas-Phase Equilibria Br- + SB = (BrSB)-, J. Am. Chem. Soc., 1991, 113, 4, 1148, https://doi.org/10.1021/ja00004a014 . [all data]

Meot-Ner and Sieck, 1986
Meot-Ner, M.; Sieck, L.W., The ionic hydrogen bond and ion solvation. 5. OH...O- bonds. Gas phase solvation and clustering of alkoxide and carboxylate anions, J. Am. Chem. Soc., 1986, 108, 7525. [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]

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]

Kebarle, 1977
Kebarle, P., Ion Thermochemistry and Solvation from Gas Phase Ion Equilibria, Ann. Rev. Phys. Chem., 1977, 28, 1, 445, https://doi.org/10.1146/annurev.pc.28.100177.002305 . [all data]

Yamdagni and Kebarle, 1971
Yamdagni, R.; Kebarle, P., Hydrogen bonding energies to negative ions from gas phase measurements of ionic equilibria, J. Am. Chem. Soc., 1971, 93, 7139. [all data]

Amunugama and Rodgers, 2002
Amunugama, R.; Rodgers, M.T., The influence of substituents on cation-pi interactions. 4. Absolute binding energies of alkali metal cation - Phenol complexes determined by threshold collision-induced dissociation and theoretical studies, J. Phys. Chem. A, 2002, 106, 42, 9718, https://doi.org/10.1021/jp0211584 . [all data]

Larson and McMahon, 1983
Larson, J.W.; McMahon, T.B., Strong hydrogen bonding in gas-phase anions. An ion cyclotron resonance determination of fluoride binding energetics to bronsted acids from gas-phase fluoride exchange equilibria measurements, J. Am. Chem. Soc., 1983, 105, 2944. [all data]

Wenthold and Squires, 1995
Wenthold, P.G.; Squires, R.R., Bond dissociation energies of F2(-) and HF2(-). A gas-phase experimental and G2 theoretical study, J. Phys. Chem., 1995, 99, 7, 2002, https://doi.org/10.1021/j100007a034 . [all data]

Arshadi, Yamdagni, et al., 1970
Arshadi, M.; Yamdagni, R.; Kebarle, P., Hydration of Halide Negative Ions in the Gas Phase. II. Comparison of Hydration Energies for the Alkali Positive and Halide Negative Ions, J. Phys. Chem., 1970, 74, 7, 1475, https://doi.org/10.1021/j100702a014 . [all data]

Armentrout and Rodgers, 2000
Armentrout, P.B.; Rodgers, M.T., An Absolute Sodium Cation Affinity Scale: Threshold Collision-Induced Dissociation Experiments and ab Initio Theory, J. Phys. Chem A, 2000, 104, 11, 2238, https://doi.org/10.1021/jp991716n . [all data]

McMahon and Ohanessian, 2000
McMahon, T.B.; Ohanessian, G., An Experimental and Ab Initio Study of the Nature of the Binding in Gas-Phase Complexes of Sodium Ions, Chem. Eur. J., 2000, 6, 16, 2931, https://doi.org/10.1002/1521-3765(20000818)6:16<2931::AID-CHEM2931>3.0.CO;2-7 . [all data]


Notes

Go To: Top, Ion clustering data, References