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, Phase change 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:
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 ± 0.14 | kcal/mol | Ccb | Cox, 1961 | ALS |
ΔfH°gas | -23.05 ± 0.15 | kcal/mol | Ccb | Andon, Biddiscombe, et al., 1960 | ALS |
ΔfH°gas | -22.5 | kcal/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 | -22.8 | kcal/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 (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
8.105 | 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 |
9.890 | 100. | ||
12.95 | 150. | ||
16.65 | 200. | ||
22.61 | 273.15 | ||
24.670 | 298.15 | ||
24.823 | 300. | ||
32.455 | 400. | ||
38.697 | 500. | ||
43.614 | 600. | ||
47.524 | 700. | ||
50.703 | 800. | ||
53.344 | 900. | ||
55.566 | 1000. | ||
57.459 | 1100. | ||
59.082 | 1200. | ||
60.483 | 1300. | ||
61.692 | 1400. | ||
62.744 | 1500. |
Phase change data
Go To: Top, Gas phase 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:
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 | 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 | 58.52 | atm | N/A | Delaunois, 1968 | Uncertainty assigned by TRC = 0.7742 atm; TRC |
Pc | 60.5000 | atm | N/A | Herz and Neukirch, 1923 | Uncertainty assigned by TRC = 0.8000 atm; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 14.1 | kcal/mol | CGC | Chickos, Hosseini, et al., 1995 | Based on data from 393. to 433. K.; AC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 16.7 ± 0.2 | kcal/mol | ME | Parsons, Rochester, et al., 1971 | Based on data from 230. to 273. K.; AC |
ΔsubH° | 16.4 | kcal/mol | N/A | Cox, 1961 | DRB |
ΔsubH° | 16.41 ± 0.12 | kcal/mol | V | Andon, Biddiscombe, et al., 1960 | ALS |
ΔsubH° | 16.4 | kcal/mol | N/A | Andon, Biddiscombe, et al., 1960 | DRB |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
12.7 | 378. | EB | Chylinski, Fras, et al., 2001 | Based on data from 363. to 391. K.; AC |
11.8 | 470. | A | Stephenson and Malanowski, 1987 | Based on data from 455. to 655. K.; AC |
13.7 | 329. | A | Stephenson and Malanowski, 1987 | Based on data from 314. to 395. K.; AC |
12.2 | 402. | A | Stephenson and Malanowski, 1987 | Based on data from 387. to 456. K.; AC |
11.2 | 464. | A | Stephenson and Malanowski, 1987 | Based on data from 449. to 526. K.; AC |
10.5 | 535. | A | Stephenson and Malanowski, 1987 | Based on data from 520. to 625. K.; AC |
12.3 | 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 |
12.3 | 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 |
11.5 | 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 (atm)
T = temperature (K)
View plot Requires a JavaScript / HTML 5 canvas capable browser.
Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
380.30 to 454.90 | 4.24117 | 1509.677 | -98.949 | Dreisbach and Shrader, 1949 | Coefficents calculated by NIST from author's data. |
Enthalpy of sublimation
ΔsubH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
15.6 ± 0.79 | 280. | HSA | Chickos, 1975 | Based on data from 263. to 298. K.; AC |
16.4 ± 0.1 | 282. to 313. | GS | Andon, Biddiscombe, et al., 1960, 2 | See also Cox and Pilcher, 1970.; AC |
16.3 | 293. | ME | Sklyarenko, Markin, et al., 1958 | Based on data from 283. to 303. K.; AC |
16.3 | 292. | N/A | Nitta and Seki, 1948 | Based on data from 270. to 313. K.; AC |
16.2 | 278. to 305. | TE | Balson, 1947 | See also Jones, 1960.; AC |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
2.7519 | 314.06 | Andon, Counsell, et al., 1963, 2 | DH |
2.8979 | 314.13 | Mastrangelo, 1957 | DH |
2.751 | 314. | Inozemtsev, Liakumovich, et al., 1972 | See also Domalski and Hearing, 1996.; AC |
2.5289 | 312.7 | Eykman, 1889 | DH |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
8.762 | 314.06 | Andon, Counsell, et al., 1963, 2 | DH |
7.96 | 314. | Bret-Dibat and Lichanot, 1989 | CAL |
8.08 | 312.7 | Eykman, 1889 | DH |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Phase change 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) | 195.3 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 187.9 | kcal/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° | 349. ± 2. | kcal/mol | AVG | N/A | Average of 6 out of 7 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 342.3 ± 2.0 | kcal/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° | 340.8 ± 1.9 | kcal/mol | CIDC | Angel and Ervin, 2004 | gas phase; B |
ΔrG° | 343.4 ± 2.0 | kcal/mol | IMRE | Cumming and Kebarle, 1978 | gas phase; B |
ΔrG° | >341.5 ± 1.8 | kcal/mol | H-TS | Richardson, Stephenson, et al., 1975 | gas phase; B |
References
Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics 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]
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.,
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
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press Inc., London, 1970, 643. [all data]
Sklyarenko, Markin, et al., 1958
Sklyarenko, S.I.; Markin, B.I.; Belyaeva, L.B.,
Zh. Fiz. Khim., 1958, 32, 1916. [all data]
Nitta and Seki, 1948
Nitta, I.; Seki, S.,
J. Chem. Soc. Jpn. Pure Chem. Sect., 1948, 69, 141. [all data]
Balson, 1947
Balson, E.W.,
Studies in vapour pressure measurement, Part III.?An effusion manometer sensitive to 5 «65533» 10?6 millimetres of mercury: vapour pressure of D.D.T. and other slightly volatile substances,
Trans. Faraday Soc., 1947, 43, 54, https://doi.org/10.1039/tf9474300054
. [all data]
Jones, 1960
Jones, A.H.,
Sublimation Pressure Data for Organic Compounds.,
J. Chem. Eng. Data, 1960, 5, 2, 196-200, https://doi.org/10.1021/je60006a019
. [all data]
Andon, Counsell, et al., 1963, 2
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]
Mastrangelo, 1957
Mastrangelo, S.V.R.,
Adiabatic calorimeter for determination of cryoscopic data,
Anal. Chem., 1957, 29(5), 841-845. [all data]
Inozemtsev, Liakumovich, et al., 1972
Inozemtsev, P.P.; Liakumovich, A.G.; Gracheva, Z.D.,
Russ. J. Phys. Chem., 1972, 46, 6, 914. [all data]
Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D.,
Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III,
J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985
. [all data]
Eykman, 1889
Eykman, J.F.,
Zur kryoskopischen Molekulargewichtsbestimmung,
Z. Physik. Chem., 1889, 4, 497-519. [all data]
Bret-Dibat and Lichanot, 1989
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]
Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G.,
Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update,
J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018
. [all data]
Lipert and Colson, 1990
Lipert, R.J.; Colson, S.D.,
Accurate ionization potentials of phenol and phenol-(H2O) from the electric field dependence of the pump-probe photoionization threshold,
J. Chem. Phys., 1990, 92, 3240. [all data]
Fuke, Yoshiuchi, et al., 1984
Fuke, K.; Yoshiuchi, H.; Kaya, K.; Achiba, Y.; Sato, K.; Kimura, K.,
Multiphoton ionization photoelectron spectroscopy and two-color multiphoton ionization threshold spectroscopy on the hydrogen bonded phenol and 7-azaindole in a supersonic jet,
Chem. Phys. Lett., 1984, 108, 179. [all data]
Fraser-Monteiro, Fraser-Monteiro, et al., 1984
Fraser-Monteiro, M.L.; Fraser-Monteiro, L.; de Wit, J.; Baer, T.,
Dissociation dynamics of energy-selected phenol ions,
J. Phys. Chem., 1984, 88, 3622. [all data]
Klasinc, Kovac, et al., 1983
Klasinc, L.; Kovac, B.; Gusten, H.,
Photoelectron spectra of acenes. Electronic structure and substituent effects,
Pure Appl. Chem., 1983, 55, 289. [all data]
Behan, Johnstone, et al., 1976
Behan, J.M.; Johnstone, R.A.W.; Bentley, T.W.,
An evaluation of empirical methods for calculating the ionization potentials of substituted benzenes,
Org. Mass Spectrom., 1976, 11, 207. [all data]
Maier and Turner, 1973
Maier, J.P.; Turner, D.W.,
Steric inhibition of resonance studied by molecular photoelectron spectroscopy Part 3. Anilines, Phenols and Related Compounds,
J. Chem. Soc. Faraday Trans. 2, 1973, 69, 521. [all data]
Henion and Kingston, 1973
Henion, J.D.; Kingston, D.G.I.,
Mass spectrometry of organic compounds. VII. Energetics of substituent isomerization in diphenyl sulfide and diphenyl ether,
J. Am. Chem. Soc., 1973, 95, 8358. [all data]
Debies and Rabalais, 1973
Debies, T.P.; Rabalais, J.W.,
Photoelectron spectra of substituted benzenes. II. Seven valence electron substituents,
J. Electron Spectrosc. Relat. Phenom., 1973, 1, 355. [all data]
Cooks, Bertrand, et al., 1973
Cooks, R.G.; Bertrand, M.; Beynon, J.H.; Rennekamp, M.E.; Setser, D.W.,
Energy partitioning data as an ion structure probe. Substituted anisoles,
J. Am. Chem. Soc., 1973, 95, 1732. [all data]
Johnstone, Mellon, et al., 1971
Johnstone, R.A.W.; Mellon, F.A.; Ward, S.D.,
On-line computer methods used in conjunction with the measurement of ionization appearance potentials,
Adv. Mass Spectrom., 1971, 5, 334. [all data]
Eland, 1969
Eland, J.H.D.,
Photoelectron spectra of conjugated hydrocarbons and heteromolecules,
Intern. J. Mass Spectrom. Ion Phys., 1969, 2, 471. [all data]
Dewar and Worley, 1969
Dewar, M.J.S.; Worley, S.D.,
Photoelectron spectra of molecules. I. Ionization potentials of some organic molecules and their interpretation,
J. Chem. Phys., 1969, 50, 654. [all data]
Watanabe, 1957
Watanabe, K.,
Ionization potentials of some molecules,
J. Chem. Phys., 1957, 26, 542. [all data]
Vilesov and Terenin, 1957
Vilesov, F.I.; Terenin, A.N.,
The photoionization of the vapors of certain organic compounds,
Dokl. Akad. Nauk SSSR, 1957, 115, 744, In original 539. [all data]
Ballard, Jones, et al., 1987
Ballard, R.E.; Jones, J.; Read, D.; Inchley, A.; Cranmer, M.,
He(I) photoelectron studies of liquids and gases,
Chem. Phys. Lett., 1987, 137, 125. [all data]
Kimura, Katsumata, et al., 1981
Kimura, K.; Katsumata, S.; Achiba, Y.; Yamazaki, T.; Iwata, S.,
Ionization energies, Ab initio assignments, and valence electronic structure for 200 molecules
in Handbook of HeI Photoelectron Spectra of Fundamental Organic Compounds, Japan Scientific Soc. Press, Tokyo, 1981. [all data]
Palmer, Moyes, et al., 1979
Palmer, M.H.; Moyes, W.; Speirs, M.; Ridyard, J.N.A.,
The electronic structure of substituted benzenes; ab initio calculations and photoelectron spectra for phenol, the methyl- and fluoro-derivatives, and the dihydroxybenzenes,
J. Mol. Struct., 1979, 52, 293. [all data]
Kobayashi, 1978
Kobayashi, T.,
A simple general tendency in photoelectron angular distributions of some monosubstituted benzenes,
Phys. Lett., 1978, 69, 105. [all data]
Kobayashi and Nagakura, 1974
Kobayashi, T.; Nagakura, S.,
Photoelectron spectra of substituted benzenes,
Bull. Chem. Soc. Jpn., 1974, 47, 2563. [all data]
Dewar, Ernstbrunner, et al., 1974
Dewar, P.S.; Ernstbrunner, E.; Gilmore, J.R.; Godfrey, M.; Mellor, J.M.,
Conformational analysis of alkyl aryl ethers and alkyl aryl sulphides by photoelectron spectroscopy,
Tetrahedron, 1974, 30, 2455. [all data]
Tajima and Tsuchiya, 1973
Tajima, S.; Tsuchiya, T.,
Energetics consideration of C5H5+ ions produced from various precursors by electron impact,
Bull. Chem. Soc. Jpn., 1973, 46, 3291. [all data]
Occolowitz and White, 1968
Occolowitz, J.L.; White, G.L.,
Energetic considerations in the assignment of some fragment ion structures,
Australian J. Chem., 1968, 21, 997. [all data]
Lifshitz and Malinovich, 1984
Lifshitz, C.; Malinovich, Y.,
Time resolved photoionization mass spectrometry in the millisecond range,
Int. J. Mass Spectrom. Ion Processes, 1984, 60, 99. [all data]
Howe and Williams, 1969
Howe, I.; Williams, D.H.,
Calculation and qualitative predictions of mass spectra. Mono- and paradisubstituted benzenes,
J. Am. Chem. Soc., 1969, 91, 7137. [all data]
Bartmess, Scott, et al., 1979
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]
Shiner, Vorner, et al., 1986
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]
Capponi, Gut, et al., 1999
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]
Angel and Ervin, 2004
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]
Cumming and Kebarle, 1978
Cumming, J.B.; Kebarle, P.,
Summary of gas phase measurements involving acids AH. Entropy changes in proton transfer reactions involving negative ions. Bond dissociation energies D(A-H) and electron affinities EA(A),
Can. J. Chem., 1978, 56, 1. [all data]
Richardson, Stephenson, et al., 1975
Richardson, J.H.; Stephenson, L.M.; Brauman, J.I.,
Photodetachment of electrons from phenoxides and thiophenoxide,
J. Am. Chem. Soc., 1975, 97, 2967. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy Cp,gas Constant pressure heat capacity of gas IE (evaluated) Recommended ionization energy Pc Critical pressure Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point Ttriple Triple point temperature ΔfH°gas Enthalpy of formation of gas 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 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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