Phenol
- Formula: C6H6O
- Molecular weight: 94.1112
- IUPAC Standard InChIKey: ISWSIDIOOBJBQZ-UHFFFAOYSA-N
- CAS Registry Number: 108-95-2
- Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript. - Isotopologues:
- Other names: Carbolic acid; Baker's P and S Liquid and Ointment; Benzenol; Hydroxybenzene; Izal; Monohydroxybenzene; Monophenol; Oxybenzene; Phenic acid; Phenyl alcohol; Phenyl hydrate; Phenyl hydroxide; Phenylic acid; Phenylic alcohol; PhOH; Benzene, hydroxy-; Acide carbolique; Baker's P & S liquid & Ointment; Fenol; Fenolo; NCI-C50124; Paoscle; Phenole; Carbolsaure; NA 2821; Phenol alcohol; Phenol, molten; Rcra waste number U188; UN 1671; UN 2312; UN 2821; Phenic alcohol; NSC 36808; Campho-Phenique Cold Sore Gel (Salt/Mix); Campho-Phenique Gel (Salt/Mix); Campho-Phenique Liquid (Salt/Mix)
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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 | -96.36 ± 0.59 | kJ/mol | Ccb | Cox, 1961 | ALS |
ΔfH°gas | -96.44 ± 0.63 | kJ/mol | Ccb | Andon, Biddiscombe, et al., 1960 | ALS |
ΔfH°gas | -94.2 | kJ/mol | N/A | Parks, Manchester, et al., 1954 | Value 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 | -95.3 | kJ/mol | N/A | Badoche, 1941 | Value 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 (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
33.91 | 50. | Kudchadker S.A., 1978 | Recommended 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 |
41.38 | 100. | ||
54.19 | 150. | ||
69.65 | 200. | ||
94.61 | 273.15 | ||
103.22 | 298.15 | ||
103.86 | 300. | ||
135.79 | 400. | ||
161.91 | 500. | ||
182.48 | 600. | ||
198.84 | 700. | ||
212.14 | 800. | ||
223.19 | 900. | ||
232.49 | 1000. | ||
240.41 | 1100. | ||
247.20 | 1200. | ||
253.06 | 1300. | ||
258.12 | 1400. | ||
262.52 | 1500. |
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 | -165.0 | kJ/mol | Ccb | Cox, 1961 | ALS |
ΔfH°solid | -165.1 ± 1.3 | kJ/mol | Ccb | Andon, Biddiscombe, et al., 1960 | ALS |
ΔfH°solid | -162.8 ± 1.0 | kJ/mol | Ccb | Parks, Manchester, et al., 1954 | ALS |
ΔfH°solid | -163.9 | kJ/mol | Ccb | Badoche, 1941 | Author's hf298_condensed=-41.49 kcal/mol; ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -3058. ± 10. | kJ/mol | AVG | N/A | Average of 6 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
S°solid,1 bar | 144.01 | J/mol*K | N/A | Andon, Counsell, et al., 1963 | DH |
S°solid,1 bar | 142.7 | J/mol*K | N/A | Parks, Huffman, et al., 1933 | Extrapolation below 90 K, 49.04 J/mol*K.; DH |
Constant pressure heat capacity of solid
Cp,solid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
127.21 | 298.15 | Nichols and Wads, 1975 | DH |
199.8 | 313. | Rastorguev and Ganiev, 1967 | T = 313 to 373 K.; DH |
127.44 | 298.15 | Andon, Counsell, et al., 1963 | T = 13 to 336 K.; DH |
93.7 | 293. | Campbell and Campbell, 1940 | DH |
103.8 | 229.3 | Aoyama and Kanda, 1935 | T = 78 to 229 K. Value is unsmoothed experimental datum.; DH |
133.09 | 295.8 | Parks, Huffman, et al., 1933 | T = 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 |
---|---|---|---|---|---|
Tboil | 455.0 ± 0.6 | K | AVG | N/A | Average of 25 out of 27 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 314. ± 1. | K | AVG | N/A | Average of 60 out of 61 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 314.06 | K | N/A | Andon, Counsell, et al., 1963, 2 | Uncertainty assigned by TRC = 0.01 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 694.3 | K | N/A | Delaunois, 1968 | Uncertainty assigned by TRC = 0.4 K; TRC |
Tc | 694.25 | K | N/A | Ambrose, 1963 | Uncertainty assigned by TRC = 0.15 K; TRC |
Tc | 692.4 | K | N/A | Radice, 1899 | Uncertainty assigned by TRC = 2. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 59.30 | bar | N/A | Delaunois, 1968 | Uncertainty assigned by TRC = 0.7845 bar; TRC |
Pc | 61.3016 | bar | N/A | Herz and Neukirch, 1923 | Uncertainty assigned by TRC = 0.8106 bar; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 58.8 | kJ/mol | CGC | Chickos, Hosseini, et al., 1995 | Based on data from 393. to 433. K.; AC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 69.7 ± 0.9 | kJ/mol | ME | Parsons, Rochester, et al., 1971 | Based on data from 230. to 273. K.; AC |
ΔsubH° | 68.6 | kJ/mol | N/A | Cox, 1961 | DRB |
ΔsubH° | 68.66 ± 0.50 | kJ/mol | V | Andon, Biddiscombe, et al., 1960 | ALS |
ΔsubH° | 68.7 | kJ/mol | N/A | Andon, Biddiscombe, et al., 1960 | DRB |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
53.2 | 378. | EB | Chylinski, Fras, et al., 2001 | Based on data from 363. to 391. K.; AC |
49.5 | 470. | A | Stephenson and Malanowski, 1987 | Based on data from 455. to 655. K.; AC |
57.4 | 329. | A | Stephenson and Malanowski, 1987 | Based on data from 314. to 395. K.; AC |
50.9 | 402. | A | Stephenson and Malanowski, 1987 | Based on data from 387. to 456. K.; AC |
46.8 | 464. | A | Stephenson and Malanowski, 1987 | Based on data from 449. to 526. K.; AC |
43.8 | 535. | A | Stephenson and Malanowski, 1987 | Based on data from 520. to 625. K.; AC |
51.3 | 398. | EB,GS | Stephenson and Malanowski, 1987 | Based on data from 383. to 473. K. See also Andon, Biddiscombe, et al., 1960, 2 and Dykyj, 1972.; AC |
51.4 | 395. | N/A | Dreisbach and Shrader, 1949 | Based on data from 380. to 455. K. See also Dreisbach and Martin, 1949 and Boublik, Fried, et al., 1984.; AC |
48.1 | 434. | N/A | Goldblum, Martin, et al., 1947 | Based on data from 414. to 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 to 454.90 | 4.24688 | 1509.677 | -98.949 | Dreisbach and Shrader, 1949 | Coefficents calculated by NIST from author's data. |
Enthalpy of sublimation
ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
65.3 ± 3.3 | 280. | HSA | Chickos, 1975 | Based on data from 263. to 298. K.; AC |
68.7 ± 0.5 | 282. to 313. | GS | Andon, Biddiscombe, et al., 1960, 2 | See also Cox and Pilcher, 1970.; AC |
68.2 | 293. | ME | Sklyarenko, Markin, et al., 1958 | Based on data from 283. to 303. K.; AC |
68.1 | 292. | N/A | Nitta and Seki, 1948 | Based on data from 270. to 313. K.; AC |
67.8 | 278. to 305. | TE | Balson, 1947 | See also Jones, 1960.; AC |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
11.514 | 314.06 | Andon, Counsell, et al., 1963 | DH |
12.125 | 314.13 | Mastrangelo, 1957 | DH |
11.51 | 314. | Inozemtsev, Liakumovich, et al., 1972 | See also Domalski and Hearing, 1996.; AC |
10.581 | 312.7 | Eykman, 1889 | DH |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
36.66 | 314.06 | Andon, Counsell, et al., 1963 | DH |
33.3 | 314. | Bret-Dibat and Lichanot, 1989 | CAL |
33.8 | 312.7 | Eykman, 1889 | DH |
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
By formula: C6H5O- + H+ = C6H6O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1462. ± 10. | kJ/mol | AVG | N/A | Average of 6 out of 7 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1432. ± 8.4 | kJ/mol | IMRE | Bartmess, Scott, et al., 1979 | gas 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° | 1426. ± 7.9 | kJ/mol | CIDC | Angel and Ervin, 2004 | gas phase; B |
ΔrG° | 1437. ± 8.4 | kJ/mol | IMRE | Cumming and Kebarle, 1978 | gas phase; B |
ΔrG° | >1429. ± 7.5 | kJ/mol | H-TS | Richardson, Stephenson, et al., 1975 | gas phase; B |
By formula: Cl- + C6H6O = (Cl- • C6H6O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 109. ± 8.4 | kJ/mol | TDAs | French, Ikuta, et al., 1982 | gas phase; B,M |
ΔrH° | 109. ± 8.4 | kJ/mol | TDEq | Cummings, French, et al., 1977 | gas phase; Re-anchored to data in French, Ikuta, et al., 1982.; B |
ΔrH° | 115. | kJ/mol | PHPMS | Kebarle, 1977 | gas phase; M |
ΔrH° | 111. | kJ/mol | PHPMS | Paul and Kebarle, 1990 | gas phase; Entropy change calculated or estimated; M |
ΔrH° | 81.2 ± 8.4 | kJ/mol | TDAs | Yamdagni and Kebarle, 1971 | gas phase; B,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 109. | J/mol*K | PHPMS | French, Ikuta, et al., 1982 | gas phase; M |
ΔrS° | 100. | J/mol*K | PHPMS | Kebarle, 1977 | gas phase; M |
ΔrS° | 100. | J/mol*K | N/A | Paul and Kebarle, 1990 | gas phase; Entropy change calculated or estimated; M |
ΔrS° | 64.9 | J/mol*K | PHPMS | Yamdagni and Kebarle, 1971 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 80.3 ± 8.4 | kJ/mol | TDAs | French, Ikuta, et al., 1982 | gas phase; B |
ΔrG° | 77.4 ± 8.4 | kJ/mol | TDEq | Cummings, French, et al., 1977 | gas phase; Re-anchored to data in French, Ikuta, et al., 1982.; B |
ΔrG° | 61.9 ± 8.4 | kJ/mol | TDAs | Yamdagni and Kebarle, 1971 | gas phase; B |
Free energy of reaction
ΔrG° (kJ/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
66.5 | 423. | PHPMS | Paul and Kebarle, 1990 | gas phase; Entropy change calculated or estimated; M |
By formula: F- + C6H6O = (F- • C6H6O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 173. ± 8.4 | kJ/mol | IMRE | Larson and McMahon, 1983 | gas 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° | 110. | J/mol*K | N/A | Larson and McMahon, 1983 | gas phase; switching reaction(F-)H2O, Entropy change calculated or estimated; Arshadi, Yamdagni, et al., 1970; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 140. ± 8.4 | kJ/mol | IMRE | Larson and McMahon, 1983 | gas 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 |
By formula: Br- + C6H6O = (Br- • C6H6O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 87.0 ± 7.5 | kJ/mol | IMRE | Paul and Kebarle, 1990 | gas phase; ΔGaff at 423 K; B,M |
ΔrH° | 82.0 | kJ/mol | PHPMS | Paul and Kebarle, 1991 | gas phase; Entropy change calculated or estimated; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 84. | J/mol*K | N/A | Paul and Kebarle, 1991 | gas phase; Entropy change calculated or estimated; M |
ΔrS° | 96. | J/mol*K | N/A | Paul and Kebarle, 1990 | gas phase; Entropy change calculated or estimated; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 46.4 ± 4.2 | kJ/mol | IMRE | Paul and Kebarle, 1990 | gas phase; ΔGaff at 423 K; B |
Free energy of reaction
ΔrG° (kJ/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
46.4 | 423. | PHPMS | Paul and Kebarle, 1991 | gas phase; Entropy change calculated or estimated; M |
46.4 | 423. | PHPMS | Paul and Kebarle, 1990 | gas phase; Entropy change calculated or estimated; M |
By formula: I- + C6H6O = (I- • C6H6O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 72.4 ± 7.5 | kJ/mol | IMRE | Paul and Kebarle, 1990 | gas phase; ΔGaff at 423 K; B,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 88. | J/mol*K | N/A | Paul and Kebarle, 1990 | gas phase; Entropy change calculated or estimated; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 35. ± 4.2 | kJ/mol | IMRE | Paul and Kebarle, 1990 | gas phase; ΔGaff at 423 K; B |
Free energy of reaction
ΔrG° (kJ/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
35. | 423. | PHPMS | Paul and Kebarle, 1990 | gas phase; Entropy change calculated or estimated; M |
By formula: C2H3O2- + C6H6O = (C2H3O2- • C6H6O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 109. ± 4.2 | kJ/mol | N/A | Meot-Ner and Sieck, 1986 | gas phase; B,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 100. | J/mol*K | PHPMS | Meot-Ner and Sieck, 1986 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 79.1 ± 6.7 | kJ/mol | TDAs | Meot-Ner and Sieck, 1986 | gas phase; B |
By formula: Na+ + C6H6O = (Na+ • C6H6O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 102. ± 3. | kJ/mol | CIDT | Amunugama and Rodgers, 2002 | RCD |
ΔrH° | 98. ± 3. | kJ/mol | CIDT | Armentrout and Rodgers, 2000 | RCD |
Free energy of reaction
ΔrG° (kJ/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
69.9 | 298. | IMRE | McMahon and Ohanessian, 2000 | Anchor alanine=39.89; RCD |
By formula: C6H6O + C12H18O = C9H12O + C9H12O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -0.7 ± 1.0 | kJ/mol | Eqk | Nesterova, Pimerzin, et al., 1989 | liquid phase; Isomerization; ALS |
ΔrH° | -0.7 ± 1.0 | kJ/mol | Eqk | Nesterova, Pilyshchikov, et al., 1983 | liquid phase; GC; ALS |
C22H20O2Ti (cr) + 2( • 5.55) (solution) = 2 (cr) + (cr)
By formula: C22H20O2Ti (cr) + 2(HCl • 5.55H2O) (solution) = 2C6H6O (cr) + C10H10Cl2Ti (cr)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -5.8 ± 2.5 | kJ/mol | RSC | Dias, Salema, et al., 1981 | Please also see Calhorda, Carrondo, et al., 1986.; MS |
(solution) + C5H11BrMg (solution) = C6H5BrMgO (solution) + (solution)
By formula: C6H6O (solution) + C5H11BrMg (solution) = C6H5BrMgO (solution) + C5H12 (solution)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -202.5 ± 4.2 | kJ/mol | RSC | Holm, 1983 | solvent: Diethyl ether; MS |
C20H32Zr (solution) + (solution) = C26H36OZr (solution) + (g)
By formula: C20H32Zr (solution) + C6H6O (solution) = C26H36OZr (solution) + H2 (g)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -132.6 ± 1.7 | kJ/mol | RSC | Schock and Marks, 1988 | solvent: Toluene; MS |
C26H36OZr (solution) + (solution) = C32H40O2Zr (solution) + (g)
By formula: C26H36OZr (solution) + C6H6O (solution) = C32H40O2Zr (solution) + H2 (g)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -86.6 ± 2.9 | kJ/mol | RSC | Schock and Marks, 1988 | solvent: Toluene; MS |
By formula: C8H8O2 + H2O = C6H6O + C2H4O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -28.7 ± 0.2 | kJ/mol | Cm | Wadso, 1960 | liquid phase; Heat of hydrolysis; ALS |
By formula: C6H6O + C14H22O = C10H14O + C10H14O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -2.6 ± 1.1 | kJ/mol | Eqk | Nesterova, Pimerzin, et al., 1989 | liquid phase; Isomerization; ALS |
+ C18H30O = +
By formula: C6H6O + C18H30O = C14H22O + C10H14O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -1.7 ± 1.5 | kJ/mol | Eqk | Nesterova, Pimerzin, et al., 1989 | liquid phase; Isomerization; ALS |
By formula: C6H6O + C14H22O = C10H14O + C10H14O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -3.2 ± 1.9 | kJ/mol | Eqk | Nesterova, Pimerzin, et al., 1989 | liquid phase; Isomerization; ALS |
By formula: C6H6O + C14H22O = 2C10H14O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -1.3 ± 2.1 | kJ/mol | Eqk | Nesterova, Pimerzin, et al., 1989 | liquid phase; Isomerization; ALS |
C6H5NaO (cr) + ( • 552) (solution) = (cr) + (cr)
By formula: C6H5NaO (cr) + (HCl • 552H2O) (solution) = C6H6O (cr) + ClNa (cr)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -78.0 ± 5.7 | kJ/mol | RSC | Leal, Pires de Matos, et al., 1991 | MS |
By formula: C6H6O + C14H22O = C10H14O + C10H14O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 0.08 ± 0.71 | kJ/mol | Eqk | Pil'shchikov, Nesterova, et al., 1981 | liquid phase; ALS |
By formula: C6H6O + C14H22O = C10H14O + C10H14O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -0. ± 4. | kJ/mol | Eqk | Pil'shchikov, Nesterova, et al., 1981 | liquid phase; ALS |
By formula: (Li+ • C6H6O) + C6H6O = (Li+ • 2C6H6O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 115. ± 3. | kJ/mol | CIDT | Amunugama and Rodgers, 2002 | RCD |
By formula: (Na+ • C6H6O) + C6H6O = (Na+ • 2C6H6O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 82. ± 3. | kJ/mol | CIDT | Amunugama and Rodgers, 2002 | RCD |
By formula: (Cs+ • C6H6O) + C6H6O = (Cs+ • 2C6H6O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 61. ± 3. | kJ/mol | CIDT | Amunugama and Rodgers, 2002 | RCD |
By formula: (Rb+ • C6H6O) + C6H6O = (Rb+ • 2C6H6O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 64. ± 3. | kJ/mol | CIDT | Amunugama and Rodgers, 2002 | RCD |
By formula: (K+ • C6H6O) + C6H6O = (K+ • 2C6H6O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 68. ± 3. | kJ/mol | CIDT | Amunugama and Rodgers, 2002 | RCD |
(cr) + C10H11ClZr (cr) = C16H15ClOZr (cr) + (g)
By formula: C6H6O (cr) + C10H11ClZr (cr) = C16H15ClOZr (cr) + H2 (g)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -77.7 ± 4.2 | kJ/mol | RSC | Diogo, Simoni, et al., 1993 | MS |
By formula: C6H6O + C14H22O = 2C10H14O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -12.8 ± 0.54 | kJ/mol | Eqk | Pil'shchikov, Nesterova, et al., 1981 | liquid phase; ALS |
By formula: C6H6O + C14H22O = C10H14O + C10H14O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 0.0 | kJ/mol | Eqk | Pil'shchikov, Nesterova, et al., 1981 | liquid phase; ALS |
C6H5NaO (cr) + (l) = (cr) + (cr)
By formula: C6H5NaO (cr) + H2O (l) = C6H6O (cr) + HNaO (cr)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 21.4 ± 3.6 | kJ/mol | RSC | Leal, Pires de Matos, et al., 1991 | MS |
By formula: Li+ + C6H6O = (Li+ • C6H6O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 178. ± 17. | kJ/mol | CIDT | Amunugama and Rodgers, 2002 | RCD |
By formula: Cs+ + C6H6O = (Cs+ • C6H6O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 66. ± 3. | kJ/mol | CIDT | Amunugama and Rodgers, 2002 | RCD |
By formula: Rb+ + C6H6O = (Rb+ • C6H6O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 69. ± 3. | kJ/mol | CIDT | Amunugama and Rodgers, 2002 | RCD |
By formula: K+ + C6H6O = (K+ • C6H6O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 74. ± 3. | kJ/mol | CIDT | Amunugama and Rodgers, 2002 | RCD |
By formula: C10H14O = C4H8 + C6H6O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 77.8 | kJ/mol | Cm | Kukui, Potolovskii, et al., 1973 | liquid phase; ALS |
By formula: C10H14O = C4H8 + C6H6O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 82.8 | kJ/mol | Cm | Kukui, Potolovskii, et al., 1973 | liquid phase; ALS |
By formula: C10H14O = C6H6O + C4H8
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 71.0 ± 2.1 | kJ/mol | Eqk | Verevkin, 1982 | gas 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 ± 0.02 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 817.3 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 786.3 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C5H5+ | 12.96 ± 0.10 | CO+H | DER | Fraser-Monteiro, Fraser-Monteiro, et al., 1984 | LBLHLM |
C5H5+ | 14.2 ± 0.2 | CO+H | EI | Tajima and Tsuchiya, 1973 | LLK |
C5H5+ | 14.25 | CO+H | EI | Occolowitz and White, 1968 | RDSH |
C5H6+ | 11.4 ± 0.1 | CO | TRPI | Lifshitz and Malinovich, 1984 | LBLHLM |
C5H6+ | 12.5 ± 0.1 | CO | EI | Henion and Kingston, 1973 | LLK |
C5H6+ | 11.67 | CO | EI | Howe and Williams, 1969 | RDSH |
C5H6+[c-C5H6] | 11.59 ± 0.10 | CO | PIPECO | Fraser-Monteiro, Fraser-Monteiro, et al., 1984 | T = 0K; LBLHLM |
De-protonation reactions
By formula: C6H5O- + H+ = C6H6O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1462. ± 10. | kJ/mol | AVG | N/A | Average of 6 out of 7 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1432. ± 8.4 | kJ/mol | IMRE | Bartmess, Scott, et al., 1979 | gas 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° | 1426. ± 7.9 | kJ/mol | CIDC | Angel and Ervin, 2004 | gas phase; B |
ΔrG° | 1437. ± 8.4 | kJ/mol | IMRE | Cumming and Kebarle, 1978 | gas phase; B |
ΔrG° | >1429. ± 7.5 | kJ/mol | H-TS | Richardson, Stephenson, et al., 1975 | gas 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
By formula: Br- + C6H6O = (Br- • C6H6O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 87.0 ± 7.5 | kJ/mol | IMRE | Paul and Kebarle, 1990 | gas phase; ΔGaff at 423 K; B,M |
ΔrH° | 82.0 | kJ/mol | PHPMS | Paul and Kebarle, 1991 | gas phase; Entropy change calculated or estimated; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 84. | J/mol*K | N/A | Paul and Kebarle, 1991 | gas phase; Entropy change calculated or estimated; M |
ΔrS° | 96. | J/mol*K | N/A | Paul and Kebarle, 1990 | gas phase; Entropy change calculated or estimated; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 46.4 ± 4.2 | kJ/mol | IMRE | Paul and Kebarle, 1990 | gas phase; ΔGaff at 423 K; B |
Free energy of reaction
ΔrG° (kJ/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
46.4 | 423. | PHPMS | Paul and Kebarle, 1991 | gas phase; Entropy change calculated or estimated; M |
46.4 | 423. | PHPMS | Paul and Kebarle, 1990 | gas phase; Entropy change calculated or estimated; M |
By formula: C2H3O2- + C6H6O = (C2H3O2- • C6H6O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 109. ± 4.2 | kJ/mol | N/A | Meot-Ner and Sieck, 1986 | gas phase; B,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 100. | J/mol*K | PHPMS | Meot-Ner and Sieck, 1986 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 79.1 ± 6.7 | kJ/mol | TDAs | Meot-Ner and Sieck, 1986 | gas phase; B |
By formula: Cl- + C6H6O = (Cl- • C6H6O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 109. ± 8.4 | kJ/mol | TDAs | French, Ikuta, et al., 1982 | gas phase; B,M |
ΔrH° | 109. ± 8.4 | kJ/mol | TDEq | Cummings, French, et al., 1977 | gas phase; Re-anchored to data in French, Ikuta, et al., 1982.; B |
ΔrH° | 115. | kJ/mol | PHPMS | Kebarle, 1977 | gas phase; M |
ΔrH° | 111. | kJ/mol | PHPMS | Paul and Kebarle, 1990 | gas phase; Entropy change calculated or estimated; M |
ΔrH° | 81.2 ± 8.4 | kJ/mol | TDAs | Yamdagni and Kebarle, 1971 | gas phase; B,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 109. | J/mol*K | PHPMS | French, Ikuta, et al., 1982 | gas phase; M |
ΔrS° | 100. | J/mol*K | PHPMS | Kebarle, 1977 | gas phase; M |
ΔrS° | 100. | J/mol*K | N/A | Paul and Kebarle, 1990 | gas phase; Entropy change calculated or estimated; M |
ΔrS° | 64.9 | J/mol*K | PHPMS | Yamdagni and Kebarle, 1971 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 80.3 ± 8.4 | kJ/mol | TDAs | French, Ikuta, et al., 1982 | gas phase; B |
ΔrG° | 77.4 ± 8.4 | kJ/mol | TDEq | Cummings, French, et al., 1977 | gas phase; Re-anchored to data in French, Ikuta, et al., 1982.; B |
ΔrG° | 61.9 ± 8.4 | kJ/mol | TDAs | Yamdagni and Kebarle, 1971 | gas phase; B |
Free energy of reaction
ΔrG° (kJ/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
66.5 | 423. | PHPMS | Paul and Kebarle, 1990 | gas phase; Entropy change calculated or estimated; M |
By formula: Cs+ + C6H6O = (Cs+ • C6H6O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 66. ± 3. | kJ/mol | CIDT | Amunugama and Rodgers, 2002 | RCD |
By formula: (Cs+ • C6H6O) + C6H6O = (Cs+ • 2C6H6O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 61. ± 3. | kJ/mol | CIDT | Amunugama and Rodgers, 2002 | RCD |
By formula: F- + C6H6O = (F- • C6H6O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 173. ± 8.4 | kJ/mol | IMRE | Larson and McMahon, 1983 | gas 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° | 110. | J/mol*K | N/A | Larson and McMahon, 1983 | gas phase; switching reaction(F-)H2O, Entropy change calculated or estimated; Arshadi, Yamdagni, et al., 1970; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 140. ± 8.4 | kJ/mol | IMRE | Larson and McMahon, 1983 | gas 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 |
By formula: I- + C6H6O = (I- • C6H6O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 72.4 ± 7.5 | kJ/mol | IMRE | Paul and Kebarle, 1990 | gas phase; ΔGaff at 423 K; B,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 88. | J/mol*K | N/A | Paul and Kebarle, 1990 | gas phase; Entropy change calculated or estimated; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 35. ± 4.2 | kJ/mol | IMRE | Paul and Kebarle, 1990 | gas phase; ΔGaff at 423 K; B |
Free energy of reaction
ΔrG° (kJ/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
35. | 423. | PHPMS | Paul and Kebarle, 1990 | gas phase; Entropy change calculated or estimated; M |
By formula: K+ + C6H6O = (K+ • C6H6O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 74. ± 3. | kJ/mol | CIDT | Amunugama and Rodgers, 2002 | RCD |
By formula: (K+ • C6H6O) + C6H6O = (K+ • 2C6H6O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 68. ± 3. | kJ/mol | CIDT | Amunugama and Rodgers, 2002 | RCD |
By formula: Li+ + C6H6O = (Li+ • C6H6O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 178. ± 17. | kJ/mol | CIDT | Amunugama and Rodgers, 2002 | RCD |
By formula: (Li+ • C6H6O) + C6H6O = (Li+ • 2C6H6O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 115. ± 3. | kJ/mol | CIDT | Amunugama and Rodgers, 2002 | RCD |
By formula: Na+ + C6H6O = (Na+ • C6H6O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 102. ± 3. | kJ/mol | CIDT | Amunugama and Rodgers, 2002 | RCD |
ΔrH° | 98. ± 3. | kJ/mol | CIDT | Armentrout and Rodgers, 2000 | RCD |
Free energy of reaction
ΔrG° (kJ/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
69.9 | 298. | IMRE | McMahon and Ohanessian, 2000 | Anchor alanine=39.89; RCD |
By formula: (Na+ • C6H6O) + C6H6O = (Na+ • 2C6H6O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 82. ± 3. | kJ/mol | CIDT | Amunugama and Rodgers, 2002 | RCD |
By formula: Rb+ + C6H6O = (Rb+ • C6H6O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 69. ± 3. | kJ/mol | CIDT | Amunugama and Rodgers, 2002 | RCD |
By formula: (Rb+ • C6H6O) + C6H6O = (Rb+ • 2C6H6O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 64. ± 3. | kJ/mol | CIDT | Amunugama and Rodgers, 2002 | RCD |
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.
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Notes
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, References
- Symbols used in this document:
AE Appearance energy Cp,gas Constant pressure heat capacity of gas Cp,solid Constant pressure heat capacity of solid IE (evaluated) Recommended ionization energy Pc Critical pressure S°solid,1 bar Entropy of solid at standard conditions (1 bar) T Temperature Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point Ttriple Triple point temperature ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔrS° Entropy of reaction at standard conditions ΔsubH Enthalpy of sublimation ΔsubH° Enthalpy of sublimation at standard conditions ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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