Home Symbol which looks like a small house Up Solid circle with an upward pointer in it

Phenol

Data at NIST subscription sites:

NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.


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
Deltar20.8 ± 1.8kcal/molIMREPaul and Kebarle, 1990gas phase; «DELTA»Gaff at 423 K; B,M
Deltar19.6kcal/molPHPMSPaul and Kebarle, 1991gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar20.cal/mol*KN/APaul and Kebarle, 1991gas phase; Entropy change calculated or estimated; M
Deltar23.cal/mol*KN/APaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar11.1 ± 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
11.1423.PHPMSPaul and Kebarle, 1991gas phase; Entropy change calculated or estimated; M
11.1423.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
Deltar26.1 ± 1.0kcal/molN/AMeot-Ner and Sieck, 1986gas phase; B,M
Quantity Value Units Method Reference Comment
Deltar24.0cal/mol*KPHPMSMeot-Ner and Sieck, 1986gas phase; M
Quantity Value Units Method Reference Comment
Deltar18.9 ± 1.6kcal/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
Deltar26.0 ± 2.0kcal/molTDAsFrench, Ikuta, et al., 1982gas phase; B,M
Deltar26.0 ± 2.0kcal/molTDEqCummings, French, et al., 1977gas phase; Re-anchored to data in French, Ikuta, et al., 1982.; B
Deltar27.4kcal/molPHPMSKebarle, 1977gas phase; M
Deltar26.5kcal/molPHPMSPaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M
Deltar19.4 ± 2.0kcal/molTDAsYamdagni and Kebarle, 1971gas phase; B,M
Quantity Value Units Method Reference Comment
Deltar26.0cal/mol*KPHPMSFrench, Ikuta, et al., 1982gas phase; M
Deltar25.cal/mol*KPHPMSKebarle, 1977gas phase; M
Deltar25.cal/mol*KN/APaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M
Deltar15.5cal/mol*KPHPMSYamdagni and Kebarle, 1971gas phase; M
Quantity Value Units Method Reference Comment
Deltar19.2 ± 2.0kcal/molTDAsFrench, Ikuta, et al., 1982gas phase; B
Deltar18.5 ± 2.0kcal/molTDEqCummings, French, et al., 1977gas phase; Re-anchored to data in French, Ikuta, et al., 1982.; B
Deltar14.8 ± 2.0kcal/molTDAsYamdagni and Kebarle, 1971gas phase; B

Free energy of reaction

DeltarG° (kcal/mol) T (K) Method Reference Comment
15.9423.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
Deltar15.7 ± 0.8kcal/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
Deltar14.5 ± 0.8kcal/molCIDTAmunugama and Rodgers, 2002RCD

Fluorine anion + Phenol = (Fluorine anion bullet Phenol)

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

Quantity Value Units Method Reference Comment
Deltar41.3 ± 2.0kcal/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
Deltar26.3cal/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
Deltar33.5 ± 2.0kcal/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
Deltar17.3 ± 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
Deltar8.4 ± 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
8.4423.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
Deltar17.7 ± 0.8kcal/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
Deltar16.3 ± 0.8kcal/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
Deltar42.6 ± 4.0kcal/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
Deltar27.4 ± 0.8kcal/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
Deltar24.4 ± 0.8kcal/molCIDTAmunugama and Rodgers, 2002RCD
Deltar23.5 ± 0.8kcal/molCIDTArmentrout and Rodgers, 2000RCD

Free energy of reaction

DeltarG° (kcal/mol) T (K) Method Reference Comment
16.7298.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
Deltar19.5 ± 0.8kcal/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
Deltar16.6 ± 0.8kcal/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
Deltar15.2 ± 0.8kcal/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