Phenol, p-tert-butyl-

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Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Henry's Law 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.

Quantity Value Units Method Reference Comment
Δfgas-186.2kJ/molEqkVerevkin, 1982Isomerization; ALS
Δfgas-214.8kJ/molN/AAmmar, El Sayed, et al., 1977Value computed using ΔfHsolid° value of -310.5±1.2 kj/mol from Ammar, El Sayed, et al., 1977 and ΔsubH° value of 95.7 kj/mol from Bertholon, Giray, et al., 1971.; DRB
Δfgas-174.3kJ/molCcbBertholon, Giray, et al., 1971ALS

Condensed phase thermochemistry data

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

Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Δfsolid-310.5 ± 1.2kJ/molCcbAmmar, El Sayed, et al., 1977 
Δfsolid-270.kJ/molCcbBertholon, Giray, et al., 1971 
Quantity Value Units Method Reference Comment
Δcsolid-5625.8 ± 1.2kJ/molCcbAmmar, El Sayed, et al., 1977Corresponding Δfsolid = -310.1 kJ/mol (simple calculation by NIST; no Washburn corrections)
Δcsolid-5669.kJ/molCcbBertholon, Giray, et al., 1971Corresponding Δfsolid = -270. kJ/mol (simple calculation by NIST; no Washburn corrections)

Phase change data

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

Data compiled as indicated in comments:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.

Quantity Value Units Method Reference Comment
Tboil507. ± 10.KAVGN/AAverage of 11 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus372. ± 2.KAVGN/AAverage of 32 out of 33 values; Individual data points
Quantity Value Units Method Reference Comment
Δvap67.9 ± 1.0kJ/molCRibeiro da Silva, Matos, et al., 1999AC
Quantity Value Units Method Reference Comment
Δsub89.4 ± 2.5kJ/molCRibeiro da Silva, Matos, et al., 1999AC
Δsub85.9 ± 0.5kJ/molGSVerevkin, 1999Based on data from 293. to 334. K.; AC
Δsub93.43kJ/molCBertholon, Giray, et al., 1971ALS
Δsub95.7kJ/molN/ABertholon, Giray, et al., 1971DRB

Enthalpy of vaporization

ΔvapH (kJ/mol) Temperature (K) Method Reference Comment
54.3486.A,GS,EBStephenson and Malanowski, 1987Based on data from 471. to 525. K. See also Stull, 1947 and Handley, Harrop, et al., 1964.; AC
59.6348.N/AStage, Müller, et al., 1953Based on data from 346. to 523. K.; AC
57.6373.N/AStage, Müller, et al., 1953Based on data from 346. to 523. K.; AC
56.6398.N/AStage, Müller, et al., 1953Based on data from 346. to 523. K.; AC
54.4423.N/AStage, Müller, et al., 1953Based on data from 346. to 523. K.; AC
49.9473.N/AStage, Müller, et al., 1953Based on data from 346. to 523. 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
471.27 to 524.84.118251622.037-118.559Handley, Harrop, et al., 1964, 2Coefficents calculated by NIST from author's data.

Enthalpy of sublimation

ΔsubH (kJ/mol) Temperature (K) Method Reference Comment
85.0 ± 0.5313.GSVerevkin, 1999Based on data from 293. to 334. K.; AC
84.3292.AStephenson and Malanowski, 1987Based on data from 280. to 304. K. See also Aihara, 1960.; AC

Enthalpy of fusion

ΔfusH (kJ/mol) Temperature (K) Reference Comment
14.52373.2Inozemtsev, Liakumovich, et al., 1972AC

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:


Henry's Law data

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

Data compiled by: Rolf Sander

Henry's Law constant (water solution)

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

H (mol/(kg*bar)) d(ln(kH))/d(1/T) (K) Method Reference Comment
890.7700.MN/AIt is assumed here that the thermodynamic data in missing citation refers to the units [mol/dm3] and [atm] as standard states.

Gas phase ion energetics data

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

Data compiled as indicated in comments:
B - John E. Bartmess
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard

Ionization energy determinations

IE (eV) Method Reference Comment
7.8PECetinkaya, Lappert, et al., 1983LBLHLM
8.16PECetinkaya, Lappert, et al., 1983Vertical value; LBLHLM

De-protonation reactions

C10H13O- + Hydrogen cation = Phenol, p-tert-butyl-

By formula: C10H13O- + H+ = C10H14O

Quantity Value Units Method Reference Comment
Δr1458. ± 8.8kJ/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Δr1429. ± 8.4kJ/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Henry's Law 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.

Verevkin, 1982
Verevkin, S.P., Study of equilibrium of tert-butylphenol dealkylation in the gas phase, Termodin. Organ. Soedin., 1982, 67-70. [all data]

Ammar, El Sayed, et al., 1977
Ammar, M.M.; El Sayed, N.; Morsi, S.E.; El Azmirly, A., The enthalpies of combustion and formation of p-tertiary butyl phenol and naphthalene, Egypt. J. Phys., 1977, 8, 111-118. [all data]

Bertholon, Giray, et al., 1971
Bertholon, G.; Giray, M.; Perrin, R.; Vincent-Falquet-Berny, M.F., No. 532. - Etude physicochimique des phenols. OX. - Ethanlpies de combustion et energies de resonance des alcoyl et aryphenols, Bull. Soc. Chim. France, 1971, 3180-3187. [all data]

Ribeiro da Silva, Matos, et al., 1999
Ribeiro da Silva, M.A.V.; Matos, M.A.R.; Morais, V.M.F.; Miranda, M.S., Thermochemical and Theoretical Study of tert -Butyl and Di- tert -butylphenol Isomers, J. Org. Chem., 1999, 64, 24, 8816-8820, https://doi.org/10.1021/jo990801o . [all data]

Verevkin, 1999
Verevkin, S.P., Thermochemistry of phenols: quantification of theortho-,para-, andmeta-interactions in tert-alkyl substituted phenols, The Journal of Chemical Thermodynamics, 1999, 31, 5, 559-585, https://doi.org/10.1006/jcht.1998.0459 . [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]

Stull, 1947
Stull, Daniel R., Vapor Pressure of Pure Substances. Organic and Inorganic Compounds, Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022 . [all data]

Handley, Harrop, et al., 1964
Handley, R.; Harrop, D.; Martin, J.F.; Sprake, C.H.S., 846. Thermodynamic properties of organic oxygen compounds. Part XIV. Purification and vapour pressures of some alkylphenols, J. Chem. Soc., 1964, 4404, https://doi.org/10.1039/jr9640004404 . [all data]

Stage, Müller, et al., 1953
Stage, H.; Müller, E.; Faldix, P., Erdol u Kohle, 1953, 6, 375. [all data]

Handley, Harrop, et al., 1964, 2
Handley, R.; Harrop, D.; Martin, J.F.; Sprake, C.H.S., Thermodynamic Properties of Organic Oxygen Compounds. Part XIV. Purification and Vapour Pressures of Some Alkylphenols, J. Chem. Soc., 1964, 4404-4406, https://doi.org/10.1039/jr9640004404 . [all data]

Aihara, 1960
Aihara, Ariyuki, Estimation of the Energy of Hydrogen Bonds Formed in Crystals. II. Phenols, Bull. Chem. Soc. Jpn., 1960, 33, 2, 194-200, https://doi.org/10.1246/bcsj.33.194 . [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]

Cetinkaya, Lappert, et al., 1983
Cetinkaya, B.; Lappert, M.F.; Suffolk, R.J., Photoelectron spectra of some sterically hindered phenols and related compounds, J. Chem. Res. Synop., 1983, 316. [all data]

Fujio, McIver, et al., 1981
Fujio, M.; McIver, R.T., Jr.; Taft, R.W., Effects on the acidities of phenols from specific substituent-solvent interactions. Inherent substituent parameters from gas phase acidities, J. Am. Chem. Soc., 1981, 103, 4017. [all data]


Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Henry's Law data, Gas phase ion energetics data, References