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Phenol, p-tert-butyl-

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Gas 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 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
Deltafgas-44.50kcal/molEqkVerevkin, 1982Isomerization; ALS
Deltafgas-51.34kcal/molN/AAmmar, El Sayed, et al., 1977Value computed using «DELTA»fHsolid° value of -310.5±1.2 kj/mol from Ammar, El Sayed, et al., 1977 and «DELTA»subH° value of 95.7 kj/mol from Bertholon, Giray, et al., 1971.; DRB
Deltafgas-41.67kcal/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
Deltafsolid-74.21 ± 0.29kcal/molCcbAmmar, El Sayed, et al., 1977 
Deltafsolid-64.kcal/molCcbBertholon, Giray, et al., 1971 
Quantity Value Units Method Reference Comment
Deltacsolid-1344.6 ± 0.29kcal/molCcbAmmar, El Sayed, et al., 1977Corresponding «DELTA»fsolid = -74.12 kcal/mol (simple calculation by NIST; no Washburn corrections)
Deltacsolid-1355.kcal/molCcbBertholon, Giray, et al., 1971Corresponding «DELTA»fsolid = -64. kcal/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, Kenneth Kroenlein 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
Deltavap16.2 ± 0.24kcal/molCRibeiro da Silva, Matos, et al., 1999AC
Quantity Value Units Method Reference Comment
Deltasub21.4 ± 0.60kcal/molCRibeiro da Silva, Matos, et al., 1999AC
Deltasub20.5 ± 0.1kcal/molGSVerevkin, 1999Based on data from 293. - 334. K.; AC
Deltasub22.33kcal/molCBertholon, Giray, et al., 1971ALS
Deltasub22.9kcal/molN/ABertholon, Giray, et al., 1971DRB

Enthalpy of vaporization

DeltavapH (kcal/mol) Temperature (K) Method Reference Comment
13.0486.A,GS,EBStephenson and Malanowski, 1987Based on data from 471. - 525. K. See also Stull, 1947 and Handley, Harrop, et al., 1964.; AC
14.2348.N/AStage, Müller, et al., 1953Based on data from 346. - 523. K.; AC
13.8373.N/AStage, Müller, et al., 1953Based on data from 346. - 523. K.; AC
13.5398.N/AStage, Müller, et al., 1953Based on data from 346. - 523. K.; AC
13.0423.N/AStage, Müller, et al., 1953Based on data from 346. - 523. K.; AC
11.9473.N/AStage, Müller, et al., 1953Based on data from 346. - 523. 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
471.27 - 524.84.112541622.037-118.559Handley, Harrop, et al., 1964, 2Coefficents calculated by NIST from author's data.

Enthalpy of sublimation

DeltasubH (kcal/mol) Temperature (K) Method Reference Comment
20.3 ± 0.1313.GSVerevkin, 1999Based on data from 293. - 334. K.; AC
20.1292.AStephenson and Malanowski, 1987Based on data from 280. - 304. K. See also Aihara, 1960.; AC

Enthalpy of fusion

DeltafusH (kcal/mol) Temperature (K) Reference Comment
3.470373.2Inozemtsev, 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:


Reaction 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 as indicated in comments:
B - John E. Bartmess
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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

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

By formula: C10H13O- + H+ = C10H14O

Quantity Value Units Method Reference Comment
Deltar348.5 ± 2.1kcal/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Deltar341.6 ± 2.0kcal/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B

Phenol, p-tert-butyl- = Phenol, m-tert-butyl-

By formula: C10H14O = C10H14O

Quantity Value Units Method Reference Comment
Deltar-0.24kcal/molEqkVerevkin, 1982gas phase; Isomerization; ALS
Deltar-0.23 ± 0.32kcal/molEqkPil'shchikov, Nesterova, et al., 1981liquid phase; ALS

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

By formula: C6H6O + C14H22O = C10H14O + C10H14O

Quantity Value Units Method Reference Comment
Deltar0.02 ± 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
Deltar-0.0 ± 0.9kcal/molEqkPil'shchikov, Nesterova, et al., 1981liquid phase; ALS

Phenol, 2,4,6-tri-tert-butyl- + Phenol, p-tert-butyl- = 22,4-Di-tert-butylphenol

By formula: C18H30O + C10H14O = 2C14H22O

Quantity Value Units Method Reference Comment
Deltar-2.96 ± 0.47kcal/molEqkPil'shchikov, Nesterova, et al., 1981liquid phase; ALS

Phenol, p-tert-butyl- = Phenol, 2-(1,1-dimethylethyl)-

By formula: C10H14O = C10H14O

Quantity Value Units Method Reference Comment
Deltar4.44 ± 0.19kcal/molEqkPil'shchikov, Nesterova, et al., 1981liquid phase; ALS

Phenol, 2-(1,1-dimethylethyl)- = Phenol, p-tert-butyl-

By formula: C10H14O = C10H14O

Quantity Value Units Method Reference Comment
Deltar-4.04 ± 0.38kcal/molEqkNesterova, Verevkin, et al., 1985liquid phase; ALS

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

By formula: C10H14O = C6H6O + C4H8

Quantity Value Units Method Reference Comment
Deltar17.0 ± 0.50kcal/molEqkVerevkin, 1982gas phase; ALS

IR Spectrum

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Mass spectrum (electron ionization), References, Notes

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

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Gas Phase Spectrum

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IR spectrum
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Additional Data

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Owner NIST Standard Reference Data Program
Collection (C) 2018 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin Sadtler Research Labs Under US-EPA Contract
State gas

This IR spectrum is from the NIST/EPA Gas-Phase Infrared Database .


Mass spectrum (electron ionization)

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, References, Notes

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

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Mass spectrum
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Additional Data

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Owner NIST Mass Spectrometry Data Center
Collection (C) 2014 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin Japan AIST/NIMC Database- Spectrum MS-NW-1815
NIST MS number 228357

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


References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), 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]

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]

Pil'shchikov, Nesterova, et al., 1981
Pil'shchikov, V.A.; Nesterova, T.N.; Rozhnov, A.M., Equilibrium in the system phenol-tert-butylphenols, J. Appl. Chem. USSR, 1981, 54, 1765-1769. [all data]

Nesterova, Verevkin, et al., 1985
Nesterova, T.N.; Verevkin, S.P.; Malova, T.N.; Pilshchikov, V.A., Study of an equilibrium of tert-alkylphenols (thermodynamic analysis of the alkylation of phenols by branched olefins), Zh. Prikl. Khim. (Leningrad), 1985, 58, 827-833. [all data]


Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), References