Phenol

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Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, 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
ΔfH°gas-23.03 ± 0.14kcal/molCcbCox, 1961ALS
ΔfH°gas-23.05 ± 0.15kcal/molCcbAndon, Biddiscombe, et al., 1960ALS
ΔfH°gas-22.5kcal/molN/AParks, Manchester, et al., 1954Value computed using ΔfHsolid° value of -162.8±1.0 kj/mol from Parks, Manchester, et al., 1954 and ΔsubH° value of 68.6 kj/mol from Cox, 1961.; DRB
ΔfH°gas-22.8kcal/molN/ABadoche, 1941Value computed using ΔfHsolid° value of -163.9 kj/mol from Badoche, 1941 and ΔsubH° value of 68.6 kj/mol from Cox, 1961.; DRB

Constant pressure heat capacity of gas

Cp,gas (cal/mol*K) Temperature (K) Reference Comment
8.10550.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
9.890100.
12.95150.
16.65200.
22.61273.15
24.670298.15
24.823300.
32.455400.
38.697500.
43.614600.
47.524700.
50.703800.
53.344900.
55.5661000.
57.4591100.
59.0821200.
60.4831300.
61.6921400.
62.7441500.

Condensed phase thermochemistry data

Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, 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
ΔfH°solid-39.44kcal/molCcbCox, 1961ALS
ΔfH°solid-39.46 ± 0.30kcal/molCcbAndon, Biddiscombe, et al., 1960ALS
ΔfH°solid-38.90 ± 0.25kcal/molCcbParks, Manchester, et al., 1954ALS
ΔfH°solid-39.18kcal/molCcbBadoche, 1941Author's hf298_condensed=-41.49 kcal/mol; ALS
Quantity Value Units Method Reference Comment
ΔcH°solid-731. ± 3.kcal/molAVGN/AAverage of 6 values; Individual data points
Quantity Value Units Method Reference Comment
S°solid,1 bar34.419cal/mol*KN/AAndon, Counsell, et al., 1963DH
S°solid,1 bar34.11cal/mol*KN/AParks, Huffman, et al., 1933Extrapolation below 90 K, 49.04 J/mol*K.; DH

Constant pressure heat capacity of solid

Cp,solid (cal/mol*K) Temperature (K) Reference Comment
30.404298.15Nichols and Wads, 1975DH
47.75313.Rastorguev and Ganiev, 1967T = 313 to 373 K.; DH
30.459298.15Andon, Counsell, et al., 1963T = 13 to 336 K.; DH
22.4293.Campbell and Campbell, 1940DH
24.81229.3Aoyama and Kanda, 1935T = 78 to 229 K. Value is unsmoothed experimental datum.; DH
31.809295.8Parks, 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, Gas phase ion energetics data, Ion clustering data, 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 25 out of 27 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus314. ± 1.KAVGN/AAverage of 60 out of 61 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
Pc58.52atmN/ADelaunois, 1968Uncertainty assigned by TRC = 0.7742 atm; TRC
Pc60.5000atmN/AHerz and Neukirch, 1923Uncertainty assigned by TRC = 0.8000 atm; TRC
Quantity Value Units Method Reference Comment
ΔvapH°14.1kcal/molCGCChickos, Hosseini, et al., 1995Based on data from 393. to 433. K.; AC
Quantity Value Units Method Reference Comment
ΔsubH°16.7 ± 0.2kcal/molMEParsons, Rochester, et al., 1971Based on data from 230. to 273. K.; AC
ΔsubH°16.4kcal/molN/ACox, 1961DRB
ΔsubH°16.41 ± 0.12kcal/molVAndon, Biddiscombe, et al., 1960ALS
ΔsubH°16.4kcal/molN/AAndon, Biddiscombe, et al., 1960DRB

Enthalpy of vaporization

ΔvapH (kcal/mol) Temperature (K) Method Reference Comment
12.7378.EBChylinski, Fras, et al., 2001Based on data from 363. to 391. K.; AC
11.8470.AStephenson and Malanowski, 1987Based on data from 455. to 655. K.; AC
13.7329.AStephenson and Malanowski, 1987Based on data from 314. to 395. K.; AC
12.2402.AStephenson and Malanowski, 1987Based on data from 387. to 456. K.; AC
11.2464.AStephenson and Malanowski, 1987Based on data from 449. to 526. K.; AC
10.5535.AStephenson and Malanowski, 1987Based on data from 520. to 625. K.; AC
12.3398.EB,GSStephenson and Malanowski, 1987Based on data from 383. to 473. K. See also Andon, Biddiscombe, et al., 1960, 2 and Dykyj, 1972.; AC
12.3395.N/ADreisbach and Shrader, 1949Based on data from 380. to 455. K. See also Dreisbach and Martin, 1949 and Boublik, Fried, et al., 1984.; AC
11.5434.N/AGoldblum, Martin, et al., 1947Based on data from 414. to 454. K.; AC

Antoine Equation Parameters

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

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Temperature (K) A B C Reference Comment
380.30 to 454.904.241171509.677-98.949Dreisbach and Shrader, 1949Coefficents calculated by NIST from author's data.

Enthalpy of sublimation

ΔsubH (kcal/mol) Temperature (K) Method Reference Comment
15.6 ± 0.79280.HSAChickos, 1975Based on data from 263. to 298. K.; AC
16.4 ± 0.1282. to 313.GSAndon, Biddiscombe, et al., 1960, 2See also Cox and Pilcher, 1970.; AC
16.3293.MESklyarenko, Markin, et al., 1958Based on data from 283. to 303. K.; AC
16.3292.N/ANitta and Seki, 1948Based on data from 270. to 313. K.; AC
16.2278. to 305.TEBalson, 1947See also Jones, 1960.; AC

Enthalpy of fusion

ΔfusH (kcal/mol) Temperature (K) Reference Comment
2.7519314.06Andon, Counsell, et al., 1963DH
2.8979314.13Mastrangelo, 1957DH
2.751314.Inozemtsev, Liakumovich, et al., 1972See also Domalski and Hearing, 1996.; AC
2.5289312.7Eykman, 1889DH

Entropy of fusion

ΔfusS (cal/mol*K) Temperature (K) Reference Comment
8.762314.06Andon, Counsell, et al., 1963DH
7.96314.Bret-Dibat and Lichanot, 1989CAL
8.08312.7Eykman, 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, Gas phase ion energetics data, Ion clustering data, 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
ΔrH°349. ± 2.kcal/molAVGN/AAverage of 6 out of 7 values; Individual data points
Quantity Value Units Method Reference Comment
ΔrG°342.3 ± 2.0kcal/molIMREBartmess, Scott, et al., 1979gas phase; Shiner, Vorner, et al., 1986: tautomer acidities ΔHacid(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
ΔrG°340.8 ± 1.9kcal/molCIDCAngel and Ervin, 2004gas phase; B
ΔrG°343.4 ± 2.0kcal/molIMRECumming and Kebarle, 1978gas phase; B
ΔrG°>341.5 ± 1.8kcal/molH-TSRichardson, Stephenson, et al., 1975gas phase; B

Chlorine anion + Phenol = (Chlorine anion • Phenol)

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

Quantity Value Units Method Reference Comment
ΔrH°26.0 ± 2.0kcal/molTDAsFrench, Ikuta, et al., 1982gas phase; B,M
ΔrH°26.0 ± 2.0kcal/molTDEqCummings, French, et al., 1977gas phase; Re-anchored to data in French, Ikuta, et al., 1982.; B
ΔrH°27.4kcal/molPHPMSKebarle, 1977gas phase; M
ΔrH°26.5kcal/molPHPMSPaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M
ΔrH°19.4 ± 2.0kcal/molTDAsYamdagni and Kebarle, 1971gas phase; B,M
Quantity Value Units Method Reference Comment
ΔrS°26.0cal/mol*KPHPMSFrench, Ikuta, et al., 1982gas phase; M
ΔrS°25.cal/mol*KPHPMSKebarle, 1977gas phase; M
ΔrS°25.cal/mol*KN/APaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M
ΔrS°15.5cal/mol*KPHPMSYamdagni and Kebarle, 1971gas phase; M
Quantity Value Units Method Reference Comment
ΔrG°19.2 ± 2.0kcal/molTDAsFrench, Ikuta, et al., 1982gas phase; B
ΔrG°18.5 ± 2.0kcal/molTDEqCummings, French, et al., 1977gas phase; Re-anchored to data in French, Ikuta, et al., 1982.; B
ΔrG°14.8 ± 2.0kcal/molTDAsYamdagni and Kebarle, 1971gas phase; B

Free energy of reaction

ΔrG° (kcal/mol) T (K) Method Reference Comment
15.9423.PHPMSPaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M

Fluorine anion + Phenol = (Fluorine anion • Phenol)

By formula: F- + C6H6O = (F- • C6H6O)

Quantity Value Units Method Reference Comment
ΔrH°41.3 ± 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
ΔrS°26.3cal/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
ΔrG°33.5 ± 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

Bromine anion + Phenol = (Bromine anion • Phenol)

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

Quantity Value Units Method Reference Comment
ΔrH°20.8 ± 1.8kcal/molIMREPaul and Kebarle, 1990gas phase; ΔGaff at 423 K; B,M
ΔrH°19.6kcal/molPHPMSPaul and Kebarle, 1991gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
ΔrS°20.cal/mol*KN/APaul and Kebarle, 1991gas phase; Entropy change calculated or estimated; M
ΔrS°23.cal/mol*KN/APaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
ΔrG°11.1 ± 1.0kcal/molIMREPaul and Kebarle, 1990gas phase; ΔGaff at 423 K; B

Free energy of reaction

ΔrG° (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

Iodide + Phenol = (Iodide • Phenol)

By formula: I- + C6H6O = (I- • C6H6O)

Quantity Value Units Method Reference Comment
ΔrH°17.3 ± 1.8kcal/molIMREPaul and Kebarle, 1990gas phase; ΔGaff at 423 K; B,M
Quantity Value Units Method Reference Comment
ΔrS°21.cal/mol*KN/APaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
ΔrG°8.4 ± 1.0kcal/molIMREPaul and Kebarle, 1990gas phase; ΔGaff at 423 K; B

Free energy of reaction

ΔrG° (kcal/mol) T (K) Method Reference Comment
8.4423.PHPMSPaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M

MeCO2 anion + Phenol = (MeCO2 anion • Phenol)

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

Quantity Value Units Method Reference Comment
ΔrH°26.1 ± 1.0kcal/molN/AMeot-Ner and Sieck, 1986gas phase; B,M
Quantity Value Units Method Reference Comment
ΔrS°24.0cal/mol*KPHPMSMeot-Ner and Sieck, 1986gas phase; M
Quantity Value Units Method Reference Comment
ΔrG°18.9 ± 1.6kcal/molTDAsMeot-Ner and Sieck, 1986gas phase; B

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

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

Quantity Value Units Method Reference Comment
ΔrH°24.4 ± 0.8kcal/molCIDTAmunugama and Rodgers, 2002RCD
ΔrH°23.5 ± 0.8kcal/molCIDTArmentrout and Rodgers, 2000RCD

Free energy of reaction

ΔrG° (kcal/mol) T (K) Method Reference Comment
16.7298.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
ΔrH°-0.2 ± 0.24kcal/molEqkNesterova, Pimerzin, et al., 1989liquid phase; Isomerization; ALS
ΔrH°-0.16 ± 0.24kcal/molEqkNesterova, Pilyshchikov, et al., 1983liquid phase; GC; ALS

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

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

Quantity Value Units Method Reference Comment
ΔrH°-1.4 ± 0.60kcal/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
ΔrH°-48.4 ± 1.0kcal/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
ΔrH°-31.69 ± 0.41kcal/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
ΔrH°-20.7 ± 0.69kcal/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
ΔrH°-6.86 ± 0.04kcal/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
ΔrH°-0.62 ± 0.26kcal/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
ΔrH°-0.41 ± 0.36kcal/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
ΔrH°-0.76 ± 0.45kcal/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
ΔrH°-0.31 ± 0.50kcal/molEqkNesterova, Pimerzin, et al., 1989liquid phase; Isomerization; ALS

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

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

Quantity Value Units Method Reference Comment
ΔrH°-18.6 ± 1.4kcal/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
ΔrH°0.02 ± 0.17kcal/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
ΔrH°-0.0 ± 0.9kcal/molEqkPil'shchikov, Nesterova, et al., 1981liquid phase; ALS

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

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

Quantity Value Units Method Reference Comment
ΔrH°27.4 ± 0.8kcal/molCIDTAmunugama and Rodgers, 2002RCD

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

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

Quantity Value Units Method Reference Comment
ΔrH°19.5 ± 0.8kcal/molCIDTAmunugama and Rodgers, 2002RCD

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

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

Quantity Value Units Method Reference Comment
ΔrH°14.5 ± 0.8kcal/molCIDTAmunugama and Rodgers, 2002RCD

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

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

Quantity Value Units Method Reference Comment
ΔrH°15.2 ± 0.8kcal/molCIDTAmunugama and Rodgers, 2002RCD

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

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

Quantity Value Units Method Reference Comment
ΔrH°16.3 ± 0.8kcal/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
ΔrH°-18.6 ± 1.0kcal/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
ΔrH°-3.05 ± 0.13kcal/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
ΔrH°0.0kcal/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
ΔrH°5.11 ± 0.86kcal/molRSCLeal, Pires de Matos, et al., 1991MS

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

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

Quantity Value Units Method Reference Comment
ΔrH°42.6 ± 4.0kcal/molCIDTAmunugama and Rodgers, 2002RCD

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

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

Quantity Value Units Method Reference Comment
ΔrH°15.7 ± 0.8kcal/molCIDTAmunugama and Rodgers, 2002RCD

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

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

Quantity Value Units Method Reference Comment
ΔrH°16.6 ± 0.8kcal/molCIDTAmunugama and Rodgers, 2002RCD

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

By formula: K+ + C6H6O = (K+ • C6H6O)

Quantity Value Units Method Reference Comment
ΔrH°17.7 ± 0.8kcal/molCIDTAmunugama and Rodgers, 2002RCD

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

By formula: C10H14O = C4H8 + C6H6O

Quantity Value Units Method Reference Comment
ΔrH°18.6kcal/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
ΔrH°19.8kcal/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
ΔrH°17.0 ± 0.50kcal/molEqkVerevkin, 1982gas phase; ALS

Gas phase ion energetics data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Ion clustering data, References, Notes

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)195.3kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity187.9kcal/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
ΔrH°349. ± 2.kcal/molAVGN/AAverage of 6 out of 7 values; Individual data points
Quantity Value Units Method Reference Comment
ΔrG°342.3 ± 2.0kcal/molIMREBartmess, Scott, et al., 1979gas phase; Shiner, Vorner, et al., 1986: tautomer acidities ΔHacid(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
ΔrG°340.8 ± 1.9kcal/molCIDCAngel and Ervin, 2004gas phase; B
ΔrG°343.4 ± 2.0kcal/molIMRECumming and Kebarle, 1978gas phase; B
ΔrG°>341.5 ± 1.8kcal/molH-TSRichardson, Stephenson, et al., 1975gas phase; B

Ion clustering data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, 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 • Phenol)

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

Quantity Value Units Method Reference Comment
ΔrH°20.8 ± 1.8kcal/molIMREPaul and Kebarle, 1990gas phase; ΔGaff at 423 K; B,M
ΔrH°19.6kcal/molPHPMSPaul and Kebarle, 1991gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
ΔrS°20.cal/mol*KN/APaul and Kebarle, 1991gas phase; Entropy change calculated or estimated; M
ΔrS°23.cal/mol*KN/APaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
ΔrG°11.1 ± 1.0kcal/molIMREPaul and Kebarle, 1990gas phase; ΔGaff at 423 K; B

Free energy of reaction

ΔrG° (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 • Phenol)

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

Quantity Value Units Method Reference Comment
ΔrH°26.1 ± 1.0kcal/molN/AMeot-Ner and Sieck, 1986gas phase; B,M
Quantity Value Units Method Reference Comment
ΔrS°24.0cal/mol*KPHPMSMeot-Ner and Sieck, 1986gas phase; M
Quantity Value Units Method Reference Comment
ΔrG°18.9 ± 1.6kcal/molTDAsMeot-Ner and Sieck, 1986gas phase; B

Chlorine anion + Phenol = (Chlorine anion • Phenol)

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

Quantity Value Units Method Reference Comment
ΔrH°26.0 ± 2.0kcal/molTDAsFrench, Ikuta, et al., 1982gas phase; B,M
ΔrH°26.0 ± 2.0kcal/molTDEqCummings, French, et al., 1977gas phase; Re-anchored to data in French, Ikuta, et al., 1982.; B
ΔrH°27.4kcal/molPHPMSKebarle, 1977gas phase; M
ΔrH°26.5kcal/molPHPMSPaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M
ΔrH°19.4 ± 2.0kcal/molTDAsYamdagni and Kebarle, 1971gas phase; B,M
Quantity Value Units Method Reference Comment
ΔrS°26.0cal/mol*KPHPMSFrench, Ikuta, et al., 1982gas phase; M
ΔrS°25.cal/mol*KPHPMSKebarle, 1977gas phase; M
ΔrS°25.cal/mol*KN/APaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M
ΔrS°15.5cal/mol*KPHPMSYamdagni and Kebarle, 1971gas phase; M
Quantity Value Units Method Reference Comment
ΔrG°19.2 ± 2.0kcal/molTDAsFrench, Ikuta, et al., 1982gas phase; B
ΔrG°18.5 ± 2.0kcal/molTDEqCummings, French, et al., 1977gas phase; Re-anchored to data in French, Ikuta, et al., 1982.; B
ΔrG°14.8 ± 2.0kcal/molTDAsYamdagni and Kebarle, 1971gas phase; B

Free energy of reaction

ΔrG° (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+) • Phenol)

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

Quantity Value Units Method Reference Comment
ΔrH°15.7 ± 0.8kcal/molCIDTAmunugama and Rodgers, 2002RCD

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

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

Quantity Value Units Method Reference Comment
ΔrH°14.5 ± 0.8kcal/molCIDTAmunugama and Rodgers, 2002RCD

Fluorine anion + Phenol = (Fluorine anion • Phenol)

By formula: F- + C6H6O = (F- • C6H6O)

Quantity Value Units Method Reference Comment
ΔrH°41.3 ± 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
ΔrS°26.3cal/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
ΔrG°33.5 ± 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 • Phenol)

By formula: I- + C6H6O = (I- • C6H6O)

Quantity Value Units Method Reference Comment
ΔrH°17.3 ± 1.8kcal/molIMREPaul and Kebarle, 1990gas phase; ΔGaff at 423 K; B,M
Quantity Value Units Method Reference Comment
ΔrS°21.cal/mol*KN/APaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
ΔrG°8.4 ± 1.0kcal/molIMREPaul and Kebarle, 1990gas phase; ΔGaff at 423 K; B

Free energy of reaction

ΔrG° (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+) • Phenol)

By formula: K+ + C6H6O = (K+ • C6H6O)

Quantity Value Units Method Reference Comment
ΔrH°17.7 ± 0.8kcal/molCIDTAmunugama and Rodgers, 2002RCD

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

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

Quantity Value Units Method Reference Comment
ΔrH°16.3 ± 0.8kcal/molCIDTAmunugama and Rodgers, 2002RCD

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

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

Quantity Value Units Method Reference Comment
ΔrH°42.6 ± 4.0kcal/molCIDTAmunugama and Rodgers, 2002RCD

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

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

Quantity Value Units Method Reference Comment
ΔrH°27.4 ± 0.8kcal/molCIDTAmunugama and Rodgers, 2002RCD

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

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

Quantity Value Units Method Reference Comment
ΔrH°24.4 ± 0.8kcal/molCIDTAmunugama and Rodgers, 2002RCD
ΔrH°23.5 ± 0.8kcal/molCIDTArmentrout and Rodgers, 2000RCD

Free energy of reaction

ΔrG° (kcal/mol) T (K) Method Reference Comment
16.7298.IMREMcMahon and Ohanessian, 2000Anchor alanine=39.89; RCD

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

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

Quantity Value Units Method Reference Comment
ΔrH°19.5 ± 0.8kcal/molCIDTAmunugama and Rodgers, 2002RCD

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

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

Quantity Value Units Method Reference Comment
ΔrH°16.6 ± 0.8kcal/molCIDTAmunugama and Rodgers, 2002RCD

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

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

Quantity Value Units Method Reference Comment
ΔrH°15.2 ± 0.8kcal/molCIDTAmunugama and Rodgers, 2002RCD

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, 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]

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

Andon, Counsell, et al., 1963
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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
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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
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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]

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

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Herz and Neukirch, 1923
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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]

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Bret-Dibat, P.; Lichanot, A., Proprietes thermodynamiques des isomeres de position de benzenes disubstitues en phase condensee, Thermochim. Acta, 1989, 147, 2, 261, https://doi.org/10.1016/0040-6031(89)85181-0 . [all data]

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Bartmess, J.E.; Scott, J.A.; McIver, R.T., Jr., The gas phase acidity scale from methanol to phenol, J. Am. Chem. Soc., 1979, 101, 6047. [all data]

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Shiner, C.S.; Vorner, P.E.; Kass, S.R., Gas phase acidities and heats of formation of 2,4- and 2,5- cyclohexadien-1-one, the keto tautomers of phenol, J. Am. Chem. Soc., 1986, 108, 5699. [all data]

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Capponi, M.; Gut, I.G.; Hellrung, B.; Persy, G.; Wirz, J., Ketonization equilibria of phenol in aqueous solution, Can. J. Chem., 1999, 77, 5-6, 605-613, https://doi.org/10.1139/v99-048 . [all data]

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Angel, L.A.; Ervin, K.M., Competitive threshold collision-induced dissociation: Gas-phase acidity and O-H bond dissociation enthalpy of phenol, J. Phys. Chem. A, 2004, 108, 40, 8346-8352, https://doi.org/10.1021/jp0474529 . [all data]

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Notes

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