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Phenol

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Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible 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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Quantity Value Units Method Reference Comment
Deltafgas-96.36 ± 0.59kJ/molCcbCox, 1961ALS
Deltafgas-96.44 ± 0.63kJ/molCcbAndon, Biddiscombe, et al., 1960ALS
Deltafgas-94.2kJ/molN/AParks, Manchester, et al., 1954Value computed using «DELTA»fHsolid° value of -162.8±1.0 kj/mol from Parks, Manchester, et al., 1954 and «DELTA»subH° value of 68.6 kj/mol from Cox, 1961.; DRB
Deltafgas-95.3kJ/molN/ABadoche, 1941Value computed using «DELTA»fHsolid° value of -163.9 kj/mol from Badoche, 1941 and «DELTA»subH° value of 68.6 kj/mol from Cox, 1961.; DRB

Constant pressure heat capacity of gas

Cp,gas (J/mol*K) Temperature (K) Reference Comment
33.9150.Kudchadker S.A., 1978Recommended S(T) and Cp(T) values are in close agreement with statistical values calculated by [ Evans J.C., 1960, Green J.H.S., 1961]. Entropy value calculated by [ Sarin V.N., 1973] agrees well with the third-law entropy at 298.15 K but not at 400 K. Statistical values calculated by [ Ramaswamy V., 1970] seem to be erroneous.; GT
41.38100.
54.19150.
69.65200.
94.61273.15
103.22298.15
103.86300.
135.79400.
161.91500.
182.48600.
198.84700.
212.14800.
223.19900.
232.491000.
240.411100.
247.201200.
253.061300.
258.121400.
262.521500.

Condensed phase thermochemistry data

Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible 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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Deltafsolid-165.0kJ/molCcbCox, 1961ALS
Deltafsolid-165.1 ± 1.3kJ/molCcbAndon, Biddiscombe, et al., 1960ALS
Deltafsolid-162.8 ± 1.0kJ/molCcbParks, Manchester, et al., 1954ALS
Deltafsolid-163.9kJ/molCcbBadoche, 1941Author's hf298_condensed=-41.49 kcal/mol; ALS
Quantity Value Units Method Reference Comment
Deltacsolid-3058. ± 10.kJ/molAVGN/AAverage of 6 values; Individual data points
Quantity Value Units Method Reference Comment
solid,1 bar144.01J/mol*KN/AAndon, Counsell, et al., 1963DH
solid,1 bar142.7J/mol*KN/AParks, Huffman, et al., 1933Extrapolation below 90 K, 49.04 J/mol*K.; DH

Constant pressure heat capacity of solid

Cp,solid (J/mol*K) Temperature (K) Reference Comment
127.21298.15Nichols and Wads, 1975DH
199.8313.Rastorguev and Ganiev, 1967T = 313 to 373 K.; DH
127.44298.15Andon, Counsell, et al., 1963T = 13 to 336 K.; DH
93.7293.Campbell and Campbell, 1940DH
103.8229.3Aoyama and Kanda, 1935T = 78 to 229 K. Value is unsmoothed experimental datum.; DH
133.09295.8Parks, Huffman, et al., 1933T = 93 to 296 K. Value is unsmoothed experimental datum.; DH

Phase change data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible 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 as indicated in comments:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny, director
BS - Robert L. Brown and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
CAL - James S. Chickos, William E. Acree, Jr., Joel F. Liebman, Students of Chem 202 (Introduction to the Literature of Chemistry), University of Missouri -- St. Louis

Quantity Value Units Method Reference Comment
Tboil455.0 ± 0.6KAVGN/AAverage of 26 out of 28 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus314. ± 1.KAVGN/AAverage of 61 out of 62 values; Individual data points
Quantity Value Units Method Reference Comment
Ttriple314.06KN/AAndon, Counsell, et al., 1963, 2Uncertainty assigned by TRC = 0.01 K; TRC
Quantity Value Units Method Reference Comment
Tc694.3KN/ADelaunois, 1968Uncertainty assigned by TRC = 0.4 K; TRC
Tc694.25KN/AAmbrose, 1963Uncertainty assigned by TRC = 0.15 K; TRC
Tc692.4KN/ARadice, 1899Uncertainty assigned by TRC = 2. K; TRC
Quantity Value Units Method Reference Comment
Pc59.30barN/ADelaunois, 1968Uncertainty assigned by TRC = 0.7845 bar; TRC
Pc61.3016barN/AHerz and Neukirch, 1923Uncertainty assigned by TRC = 0.8106 bar; TRC
Quantity Value Units Method Reference Comment
Deltavap58.8kJ/molCGCChickos, Hosseini, et al., 1995Based on data from 393. - 433. K.; AC
Quantity Value Units Method Reference Comment
Deltasub69.7 ± 0.9kJ/molMEParsons, Rochester, et al., 1971Based on data from 230. - 273. K.; AC
Deltasub68.6kJ/molN/ACox, 1961DRB
Deltasub68.66 ± 0.50kJ/molVAndon, Biddiscombe, et al., 1960ALS
Deltasub68.7kJ/molN/AAndon, Biddiscombe, et al., 1960DRB

Enthalpy of vaporization

DeltavapH (kJ/mol) Temperature (K) Method Reference Comment
53.2378.EBChylinski, Fras, et al., 2001Based on data from 363. - 391. K.; AC
49.5470.AStephenson and Malanowski, 1987Based on data from 455. - 655. K.; AC
57.4329.AStephenson and Malanowski, 1987Based on data from 314. - 395. K.; AC
50.9402.AStephenson and Malanowski, 1987Based on data from 387. - 456. K.; AC
46.8464.AStephenson and Malanowski, 1987Based on data from 449. - 526. K.; AC
43.8535.AStephenson and Malanowski, 1987Based on data from 520. - 625. K.; AC
51.3398.EB,GSStephenson and Malanowski, 1987Based on data from 383. - 473. K. See also Andon, Biddiscombe, et al., 1960, 2 and Dykyj, 1972.; AC
51.4395.N/ADreisbach and Shrader, 1949Based on data from 380. - 455. K. See also Dreisbach and Martin, 1949 and Boublik, Fried, et al., 1984.; AC
48.1434.N/AGoldblum, Martin, et al., 1947Based on data from 414. - 454. K.; AC

Antoine Equation Parameters

log10(P) = A − (B / (T + C))
    P = vapor pressure (bar)
    T = temperature (K)

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Temperature (K) A B C Reference Comment
380.30 - 454.904.246881509.677-98.949Dreisbach and Shrader, 1949Coefficents calculated by NIST from author's data.

Enthalpy of sublimation

DeltasubH (kJ/mol) Temperature (K) Method Reference Comment
65.3 ± 3.3280.HSAChickos, 1975Based on data from 263. - 298. K.; AC
68.7 ± 0.5282. - 313.GSAndon, Biddiscombe, et al., 1960, 2See also Cox and Pilcher, 1970.; AC
68.2293.MESklyarenko, Markin, et al., 1958Based on data from 283. - 303. K.; AC
68.1292.N/ANitta and Seki, 1948Based on data from 270. - 313. K.; AC
67.8278. - 305.TEBalson, 1947See also Jones, 1960.; AC

Enthalpy of fusion

DeltafusH (kJ/mol) Temperature (K) Reference Comment
11.514314.06Andon, Counsell, et al., 1963DH
12.125314.13Mastrangelo, 1957DH
11.51314.Inozemtsev, Liakumovich, et al., 1972See also Domalski and Hearing, 1996.; AC
10.581312.7Eykman, 1889DH

Entropy of fusion

DeltafusS (J/mol*K) Temperature (K) Reference Comment
36.66314.06Andon, Counsell, et al., 1963DH
33.3314.Bret-Dibat and Lichanot, 1989CAL
33.8312.7Eykman, 1889DH

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


Reaction thermochemistry data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Henry's Law data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible 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 as indicated in comments:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
RCD - Robert C. Dunbar
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
MS - José A. Martinho Simões

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

phenoxide anion + Hydrogen cation = Phenol

By formula: C6H5O- + H+ = C6H6O

Quantity Value Units Method Reference Comment
Deltar1462. ± 10.kJ/molAVGN/AAverage of 6 out of 7 values; Individual data points
Quantity Value Units Method Reference Comment
Deltar1432. ± 8.4kJ/molIMREBartmess, Scott, et al., 1979gas phase; Shiner, Vorner, et al., 1986: tautomer acidities «DELTA»Hacid(ortho) = 343.9±3.1 kcal, para = 340.1±2 kcal. However, Capponi, Gut, et al., 1999 based on aq. soln. results, imply 18 and 14 kcal/mol difference.; value altered from reference due to change in acidity scale; B
Deltar1426. ± 7.9kJ/molCIDCAngel and Ervin, 2004gas phase; B
Deltar1437. ± 8.4kJ/molIMRECumming and Kebarle, 1978gas phase; B
Deltar>1429. ± 7.5kJ/molH-TSRichardson, Stephenson, et al., 1975gas 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

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

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

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

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

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

Phenol + Phenol, 2,4-bis(1-methylethyl)- = Phenol, 2-(1-methylethyl)- + p-Cumenol

By formula: C6H6O + C12H18O = C9H12O + C9H12O

Quantity Value Units Method Reference Comment
Deltar-0.7 ± 1.0kJ/molEqkNesterova, Pimerzin, et al., 1989liquid phase; Isomerization; ALS
Deltar-0.7 ± 1.0kJ/molEqkNesterova, Pilyshchikov, et al., 1983liquid phase; GC; ALS

C22H20O2Ti (cr) + 2(Hydrogen chloride bullet 5.55Water) (solution) = 2Phenol (cr) + Titanocene dichloride (cr)

By formula: C22H20O2Ti (cr) + 2(HCl bullet 5.55H2O) (solution) = 2C6H6O (cr) + C10H10Cl2Ti (cr)

Quantity Value Units Method Reference Comment
Deltar-5.8 ± 2.5kJ/molRSCDias, Salema, et al., 1981Please also see Calhorda, Carrondo, et al., 1986.; MS

Phenol (solution) + C5H11BrMg (solution) = C6H5BrMgO (solution) + Pentane (solution)

By formula: C6H6O (solution) + C5H11BrMg (solution) = C6H5BrMgO (solution) + C5H12 (solution)

Quantity Value Units Method Reference Comment
Deltar-202.5 ± 4.2kJ/molRSCHolm, 1983solvent: Diethyl ether; MS

C20H32Zr (solution) + Phenol (solution) = C26H36OZr (solution) + Hydrogen (g)

By formula: C20H32Zr (solution) + C6H6O (solution) = C26H36OZr (solution) + H2 (g)

Quantity Value Units Method Reference Comment
Deltar-132.6 ± 1.7kJ/molRSCSchock and Marks, 1988solvent: Toluene; MS

C26H36OZr (solution) + Phenol (solution) = C32H40O2Zr (solution) + Hydrogen (g)

By formula: C26H36OZr (solution) + C6H6O (solution) = C32H40O2Zr (solution) + H2 (g)

Quantity Value Units Method Reference Comment
Deltar-86.6 ± 2.9kJ/molRSCSchock and Marks, 1988solvent: Toluene; MS

Acetic acid, phenyl ester + Water = Phenol + Acetic acid

By formula: C8H8O2 + H2O = C6H6O + C2H4O2

Quantity Value Units Method Reference Comment
Deltar-28.7 ± 0.2kJ/molCmWadso, 1960liquid phase; Heat of hydrolysis; ALS

Phenol + Phenol, 2,5-bis(1-methylpropyl)- = Phenol, 3-(1-methylpropyl)- + Phenol, 2-(1-methylpropyl)-

By formula: C6H6O + C14H22O = C10H14O + C10H14O

Quantity Value Units Method Reference Comment
Deltar-2.6 ± 1.1kJ/molEqkNesterova, Pimerzin, et al., 1989liquid phase; Isomerization; ALS

Phenol + C18H30O = Phenol, 2,4-bis(1-methylpropyl)- + Phenol, 2-(1-methylpropyl)-

By formula: C6H6O + C18H30O = C14H22O + C10H14O

Quantity Value Units Method Reference Comment
Deltar-1.7 ± 1.5kJ/molEqkNesterova, Pimerzin, et al., 1989liquid phase; Isomerization; ALS

Phenol + Phenol, 2,4-bis(1-methylpropyl)- = Phenol, 2-(1-methylpropyl)- + Phenol, 4-(1-methylpropyl)-

By formula: C6H6O + C14H22O = C10H14O + C10H14O

Quantity Value Units Method Reference Comment
Deltar-3.2 ± 1.9kJ/molEqkNesterova, Pimerzin, et al., 1989liquid phase; Isomerization; ALS

Phenol + 3,5-Bis(2-butyl)phenol = 2Phenol, 3-(1-methylpropyl)-

By formula: C6H6O + C14H22O = 2C10H14O

Quantity Value Units Method Reference Comment
Deltar-1.3 ± 2.1kJ/molEqkNesterova, Pimerzin, et al., 1989liquid phase; Isomerization; ALS

C6H5NaO (cr) + (Hydrogen chloride bullet 552Water) (solution) = Phenol (cr) + sodium chloride (cr)

By formula: C6H5NaO (cr) + (HCl bullet 552H2O) (solution) = C6H6O (cr) + ClNa (cr)

Quantity Value Units Method Reference Comment
Deltar-78.0 ± 5.7kJ/molRSCLeal, Pires de Matos, et al., 1991MS

Phenol + Phenol, 3,5-bis(1,1-dimethylethyl)- = Phenol, m-tert-butyl- + Phenol, p-tert-butyl-

By formula: C6H6O + C14H22O = C10H14O + C10H14O

Quantity Value Units Method Reference Comment
Deltar0.08 ± 0.71kJ/molEqkPil'shchikov, Nesterova, et al., 1981liquid phase; ALS

Phenol + 2,4-Di-tert-butylphenol = Phenol, 2-(1,1-dimethylethyl)- + Phenol, p-tert-butyl-

By formula: C6H6O + C14H22O = C10H14O + C10H14O

Quantity Value Units Method Reference Comment
Deltar-0. ± 4.kJ/molEqkPil'shchikov, Nesterova, et al., 1981liquid phase; ALS

(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+) 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

(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

(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

(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

Phenol (cr) + C10H11ClZr (cr) = C16H15ClOZr (cr) + Hydrogen (g)

By formula: C6H6O (cr) + C10H11ClZr (cr) = C16H15ClOZr (cr) + H2 (g)

Quantity Value Units Method Reference Comment
Deltar-77.7 ± 4.2kJ/molRSCDiogo, Simoni, et al., 1993MS

Phenol + Phenol, 2,6-bis(1,1-dimethylethyl)- = 2Phenol, 2-(1,1-dimethylethyl)-

By formula: C6H6O + C14H22O = 2C10H14O

Quantity Value Units Method Reference Comment
Deltar-12.8 ± 0.54kJ/molEqkPil'shchikov, Nesterova, et al., 1981liquid phase; ALS

Phenol + Phenol, 2,5-bis(1,1-dimethylethyl)- = Phenol, m-tert-butyl- + Phenol, 2-(1,1-dimethylethyl)-

By formula: C6H6O + C14H22O = C10H14O + C10H14O

Quantity Value Units Method Reference Comment
Deltar0.0kJ/molEqkPil'shchikov, Nesterova, et al., 1981liquid phase; ALS

C6H5NaO (cr) + Water (l) = Phenol (cr) + Sodium hydroxide (cr)

By formula: C6H5NaO (cr) + H2O (l) = C6H6O (cr) + HNaO (cr)

Quantity Value Units Method Reference Comment
Deltar21.4 ± 3.6kJ/molRSCLeal, Pires de Matos, et al., 1991MS

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

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

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

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

Phenol, 2-(1-methylpropyl)- = 1-Butene + Phenol

By formula: C10H14O = C4H8 + C6H6O

Quantity Value Units Method Reference Comment
Deltar77.8kJ/molCmKukui, Potolovskii, et al., 1973liquid phase; ALS

Phenol, 4-(1-methylpropyl)- = 1-Butene + Phenol

By formula: C10H14O = C4H8 + C6H6O

Quantity Value Units Method Reference Comment
Deltar82.8kJ/molCmKukui, Potolovskii, et al., 1973liquid phase; ALS

Phenol, p-tert-butyl- = Phenol + 1-Propene, 2-methyl-

By formula: C10H14O = C6H6O + C4H8

Quantity Value Units Method Reference Comment
Deltar71.0 ± 2.1kJ/molEqkVerevkin, 1982gas phase; ALS

Henry's Law 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: Rolf Sander

Henry's Law constant (water solution)

kH(T) = H exp(d(ln(kH))/d(1/T) ((1/T) - 1/(298.15 K)))
H = Henry's law constant for solubility in water at 298.15 K (mol/kg*bar)
d(ln(kH))/d(1/T) = Temperature dependence constant (K)

H (mol/kg*bar) d(ln(kH))/d(1/T) (K) Method Reference Comment
3000. XN/A 
0.078 XHowe, Mullins, et al., 1987Value given here as quoted by missing citation.
190.3600.XN/A 
3000. XN/AValue given here as quoted by missing citation.
1900.7300.XN/A 
2900.6800.MN/AIt is assumed here that the thermodynamic data in missing citation refers to the units [mol/dm3] and [atm] as standard states.
490. RN/A 

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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
L - Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
LL - Sharon G. Lias and Joel F. Liebman
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

View reactions leading to C6H6O+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
IE (evaluated)8.49 ± 0.02eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)817.3kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity786.3kJ/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
8.508 ± 0.001PILipert and Colson, 1990LL
8.506 ± 0.001PIFuke, Yoshiuchi, et al., 1984LBLHLM
8.49PEFuke, Yoshiuchi, et al., 1984LBLHLM
8. ± 0.PIPECOFraser-Monteiro, Fraser-Monteiro, et al., 1984LBLHLM
~8.21PEKlasinc, Kovac, et al., 1983LBLHLM
8.55PEBehan, Johnstone, et al., 1976LLK
8.47 ± 0.02PEMaier and Turner, 1973LLK
9.1 ± 0.1EIHenion and Kingston, 1973LLK
8.37PEDebies and Rabalais, 1973LLK
8.50EICooks, Bertrand, et al., 1973LLK
8.69EIJohnstone, Mellon, et al., 1971LLK
8.48 ± 0.05PEEland, 1969RDSH
8.52PEDewar and Worley, 1969RDSH
8.50 ± 0.01PIWatanabe, 1957RDSH
8.52 ± 0.02PIVilesov and Terenin, 1957RDSH
8.75PEBallard, Jones, et al., 1987Vertical value; LBLHLM
8.61PEKlasinc, Kovac, et al., 1983Vertical value; LBLHLM
8.70PEKimura, Katsumata, et al., 1981Vertical value; LLK
8.56PEPalmer, Moyes, et al., 1979Vertical value; LLK
8.69PEKobayashi, 1978Vertical value; LLK
8.73PEKobayashi and Nagakura, 1974Vertical value; LLK
8.67PEDewar, Ernstbrunner, et al., 1974Vertical value; LLK
8.56PEDebies and Rabalais, 1973Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C5H5+12.96 ± 0.10CO+HDERFraser-Monteiro, Fraser-Monteiro, et al., 1984LBLHLM
C5H5+14.2 ± 0.2CO+HEITajima and Tsuchiya, 1973LLK
C5H5+14.25CO+HEIOccolowitz and White, 1968RDSH
C5H6+11.4 ± 0.1COTRPILifshitz and Malinovich, 1984LBLHLM
C5H6+12.5 ± 0.1COEIHenion and Kingston, 1973LLK
C5H6+11.67COEIHowe and Williams, 1969RDSH
C5H6+[c-C5H6]11.59 ± 0.10COPIPECOFraser-Monteiro, Fraser-Monteiro, et al., 1984T = 0K; LBLHLM

De-protonation reactions

phenoxide anion + Hydrogen cation = Phenol

By formula: C6H5O- + H+ = C6H6O

Quantity Value Units Method Reference Comment
Deltar1462. ± 10.kJ/molAVGN/AAverage of 6 out of 7 values; Individual data points
Quantity Value Units Method Reference Comment
Deltar1432. ± 8.4kJ/molIMREBartmess, Scott, et al., 1979gas phase; Shiner, Vorner, et al., 1986: tautomer acidities «DELTA»Hacid(ortho) = 343.9±3.1 kcal, para = 340.1±2 kcal. However, Capponi, Gut, et al., 1999 based on aq. soln. results, imply 18 and 14 kcal/mol difference.; value altered from reference due to change in acidity scale; B
Deltar1426. ± 7.9kJ/molCIDCAngel and Ervin, 2004gas phase; B
Deltar1437. ± 8.4kJ/molIMRECumming and Kebarle, 1978gas phase; B
Deltar>1429. ± 7.5kJ/molH-TSRichardson, Stephenson, et al., 1975gas phase; B

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
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

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)

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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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Mass 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 NIST Mass Spectrometry Data Center, 1994
NIST MS number 133909

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


UV/Visible spectrum

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), 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: Victor Talrose, Eugeny B. Stern, Antonina A. Goncharova, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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UVVis spectrum
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Additional Data

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Source Martynoff, 1949
Owner INEP CP RAS, NIST OSRD
Collection (C) 2007 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS
Source reference RAS UV No. 5027
Instrument n.i.g.
Melting point 40.9
Boiling point 181.8

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Notes

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

Cox, 1961
Cox, J.D., The heats of combustion of phenol and the three cresols, Pure Appl. Chem., 1961, 2, 125-128. [all data]

Andon, Biddiscombe, et al., 1960
Andon, R.J.L.; Biddiscombe, D.P.; Cox, J.D.; Handley, R.; Harrop, D.; Herington, E.F.G.; Martin, J.F., Thermodynamic properties of organic oxygen compounds. Part I. Preparation and physical properties of pure phenol, cresols, and xylenols, J. Chem. Soc., 1960, 5246-5254. [all data]

Parks, Manchester, et al., 1954
Parks, G.S.; Manchester, K.E.; Vaughan, L.M., Heats of combustion and formation of some alcohols, phenols, and ketones, J. Chem. Phys., 1954, 22, 2089-2090. [all data]

Badoche, 1941
Badoche, M., No 19. - Chaleurs de combustion du phenol, du-m-cresol et del leurs ethers; par M. Marius BADOCHE., Bull. Soc. Chim. Fr., 1941, 8, 212-220. [all data]

Kudchadker S.A., 1978
Kudchadker S.A., Ideal gas thermodynamic properties of phenol and cresols, J. Phys. Chem. Ref. Data, 1978, 7, 417-423. [all data]

Evans J.C., 1960
Evans J.C., The vibrational spectra phenol and phenol-OD, Spectrochim. Acta, 1960, 16, 1382-1392. [all data]

Green J.H.S., 1961
Green J.H.S., The thermodynamic properties of organic oxygen compounds. II. Vibrational assignment and calculated thermodynamic properties of phenol, J. Chem. Soc., 1961, 2236-2241. [all data]

Sarin V.N., 1973
Sarin V.N., Thermodynamic properties in the gaseous state of certain monosubstituted benzenes, Thermochim. Acta, 1973, 6, 39-46. [all data]

Ramaswamy V., 1970
Ramaswamy V., Thermo data for n-alkyl phenols, Hydrocarbon Process., 1970, 49, 217-218. [all data]

Andon, Counsell, et al., 1963
Andon, R.J.L.; Counsell, J.F.; Herington, E.F.G.; Martin, J.F., Thermodynamic properties of organic oxygen compounds, Trans. Faraday Soc., 1963, 59, 830-835. [all data]

Parks, Huffman, et al., 1933
Parks, G.S.; Huffman, H.M.; Barmore, M., Thermal data on organic compounds. XI. The heat capacities, entropies and free energies of ten compounds containing oxygen or nitrogen. J. Am. Chem. Soc., 1933, 55, 2733-2740. [all data]

Nichols and Wads, 1975
Nichols, N.; Wads, I., Thermochemistry of solutions of biochemical model compounds. 3. Some benzene derivatives in aqueous solution, J. Chem. Thermodynam., 1975, 7, 329-336. [all data]

Rastorguev and Ganiev, 1967
Rastorguev, Yu.L.; Ganiev, Yu.A., Study of the heat capacity of selected solvents, Izv. Vyssh. Uchebn. Zaved. Neft Gaz. 10, 1967, No.1, 79-82. [all data]

Campbell and Campbell, 1940
Campbell, A.N.; Campbell, A.J.R., The heats of solution, heats of formation, specific heats and equilibrium diagrams of certain molecular compounds. J. Am. Chem. Soc., 1940, 62, 291-297. [all data]

Aoyama and Kanda, 1935
Aoyama, S.; Kanda, E., Studies on the heat capacities at low temperature. Report I. Heat capacities of some organic substances at low temperature, Sci. Rept. Tohoku Imp. Univ. [1]24, 1935, 107-115. [all data]

Andon, Counsell, et al., 1963, 2
Andon, R.J.L.; Counsell, J.F.; Herington, E.F.G.; Martin, J.F., Thermodyn. prop. of organic oxygen compds., part 7- calorimetric study of phenol from 12 to330o K, Trans. Faraday Soc., 1963, 59, 830. [all data]

Delaunois, 1968
Delaunois, C., Effect of the Filling Rate of a Reactor on the Vapor Tension and the Temperature at the Beginning of Cracking of Phenols at High Pressures, Ann. Mines Belg., 1968, No. 1, 9-16. [all data]

Ambrose, 1963
Ambrose, D., Critical Temperatures of Some Phenols and Other Organic Compounds, Trans. Faraday Soc., 1963, 59, 1988. [all data]

Radice, 1899
Radice, G., , Ph. D. Thesis, Univ. of Geneve, 1899. [all data]

Herz and Neukirch, 1923
Herz, W.; Neukirch, E., On Knowldge of the Critical State, Z. Phys. Chem., Stoechiom. Verwandtschaftsl., 1923, 104, 433-50. [all data]

Chickos, Hosseini, et al., 1995
Chickos, James S.; Hosseini, Sarah; Hesse, Donald G., Determination of vaporization enthalpies of simple organic molecules by correlations of changes in gas chromatographic net retention times, Thermochimica Acta, 1995, 249, 41-62, https://doi.org/10.1016/0040-6031(95)90670-3 . [all data]

Parsons, Rochester, et al., 1971
Parsons, G.H.; Rochester, C.H.; Wood, C.E.C., Effect of 4-substitution on the thermodynamics of hydration of phenol and the phenoxide anion, J. Chem. Soc., B:, 1971, 533, https://doi.org/10.1039/j29710000533 . [all data]

Chylinski, Fras, et al., 2001
Chylinski, K.; Fras, Z.; Malanowski, S.K., Vapor-Liquid Equilibrium in Phenol + 2-Ethoxyethanol at 363.15 to 383.15 K, J. Chem. Eng. Data, 2001, 46, 1, 29-33, https://doi.org/10.1021/je0001072 . [all data]

Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw, Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2 . [all data]

Andon, Biddiscombe, et al., 1960, 2
Andon, R.J.L.; Biddiscombe, D.P.; Cox, J.D.; Handley, R.; Harrop, D.; Herington, E.F.G.; Martin, J.F., 1009. Thermodynamic properties of organic oxygen compounds. Part I. Preparation and physical properties of pure phenol, cresols, and xylenols, J. Chem. Soc., 1960, 5246, https://doi.org/10.1039/jr9600005246 . [all data]

Dykyj, 1972
Dykyj, J., Petrochemia, 1972, 12, 1, 13. [all data]

Dreisbach and Shrader, 1949
Dreisbach, R.R.; Shrader, S.A., Vapor Pressure--Temperature Data on Some Organic Compounds, Ind. Eng. Chem., 1949, 41, 12, 2879-2880, https://doi.org/10.1021/ie50480a054 . [all data]

Dreisbach and Martin, 1949
Dreisbach, R.R.; Martin, R.A., Physical Data on Some Organic Compounds, Ind. Eng. Chem., 1949, 41, 12, 2875-2878, https://doi.org/10.1021/ie50480a053 . [all data]

Boublik, Fried, et al., 1984
Boublik, T.; Fried, V.; Hala, E., The Vapour Pressures of Pure Substances: Selected Values of the Temperature Dependence of the Vapour Pressures of Some Pure Substances in the Normal and Low Pressure Region, 2nd ed., Elsevier, New York, 1984, 972. [all data]

Goldblum, Martin, et al., 1947
Goldblum, K.B.; Martin, R.W.; Young, R.B., Vapor Pressure Data for Phenols, Ind. Eng. Chem., 1947, 39, 11, 1474-1476, https://doi.org/10.1021/ie50455a017 . [all data]

Chickos, 1975
Chickos, James Speros, A simple equilibrium method for determining heats of sublimation, J. Chem. Educ., 1975, 52, 2, 134-39, https://doi.org/10.1021/ed052p134 . [all data]

Cox and Pilcher, 1970
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Notes

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