Phenol, 2,4,6-tri-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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Δfgas-88.39kcal/molCcbBertholon, Giray, et al., 1971 

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-119.kcal/molCcbBertholon, Giray, et al., 1971 
Quantity Value Units Method Reference Comment
Δcsolid-2598.kcal/molCcbBertholon, Giray, et al., 1971Corresponding Δfsolid = -120. 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, 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.
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
Tboil551.2KN/AWeast and Grasselli, 1989BS
Quantity Value Units Method Reference Comment
Tfus402.8KN/AChickos, Braton, et al., 1991Uncertainty assigned by TRC = 1. K; TRC
Tfus405.7KN/AInozemtsev, Liakumovich, et al., 1972Uncertainty assigned by TRC = 0.2 K; TRC
Tfus404.KN/ADavies and Kybett, 1965Uncertainty assigned by TRC = 2.5 K; TRC
Quantity Value Units Method Reference Comment
Δsub20.9 ± 0.1kcal/molGSVerevkin, 1999AC
Δsub30.61kcal/molCBertholon, Giray, et al., 1971ALS
Δsub30.64kcal/molN/ABertholon, Giray, et al., 1971DRB
Δsub20.46 ± 0.10kcal/molVDavies and Kybett, 1965ALS
Δsub20.1 ± 0.1kcal/molVAihara, 1960See also Verevkin, 1999.; AC

Enthalpy of vaporization

ΔvapH (kcal/mol) Temperature (K) Method Reference Comment
15.1430.AStephenson and Malanowski, 1987Based on data from 415. to 551. K.; AC

Enthalpy of sublimation

ΔsubH (kcal/mol) Temperature (K) Method Reference Comment
20.5 ± 0.1317.MEDavies and Kybett, 1965Based on data from 295. to 339. K. See also Stephenson and Malanowski, 1987.; AC
20.1302.N/AAihara, 1960Based on data from 292. to 313. K.; AC

Enthalpy of fusion

ΔfusH (kcal/mol) Temperature (K) Reference Comment
4.651405.2Chickos, Braton, et al., 1991, 2AC

Entropy of fusion

ΔfusS (cal/mol*K) Temperature (K) Reference Comment
5.177405.2Chickos, Braton, et al., 1991CAL

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 by: 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

Phenol, 2,4,6-tri-tert-butyl- + Phenol, 2-(1,1-dimethylethyl)- = Phenol, 2,6-bis(1,1-dimethylethyl)- + 2,4-Di-tert-butylphenol

By formula: C18H30O + C10H14O = C14H22O + C14H22O

Quantity Value Units Method Reference Comment
Δr0.03 ± 0.11kcal/molEqkPil'shchikov, Nesterova, et al., 1981liquid phase

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
Δr-2.96 ± 0.47kcal/molEqkPil'shchikov, Nesterova, et al., 1981liquid phase

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:
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
7.5PECetinkaya, Lappert, et al., 1983LBLHLM
7.82PECetinkaya, Lappert, et al., 1983Vertical value; LBLHLM

IR Spectrum

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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: 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 NIST Mass Spectrometry Data Center
State gas
Instrument HP-GC/MS/IRD

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


Mass spectrum (electron ionization)

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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: 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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Due to licensing restrictions, this spectrum cannot be downloaded.

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-5876
NIST MS number 233193

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.


UV/Visible spectrum

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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: Victor Talrose, Eugeny B. Stern, Antonina A. Goncharova, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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UVVis spectrum
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Additional Data

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Source missing citation
Owner INEP CP RAS, NIST OSRD
Collection (C) 2007 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS
Source reference RAS UV No. 8994
Instrument Unicam SP 700
Melting point 131
Boiling point 278

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Notes

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

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]

Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]

Chickos, Braton, et al., 1991
Chickos, J.S.; Braton, C.M.; Hesse, D.G.; Liebman, J.F., Estimating entropies and enthalpies of fusion of organic compounds, J. Org. Chem., 1991, 56, 3, 927, https://doi.org/10.1021/jo00003a007 . [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]

Davies and Kybett, 1965
Davies, M.; Kybett, B., Sublimation and vaporization heats of long-chain alcohols, Trans. Faraday Soc., 1965, 61, 1608. [all data]

Verevkin, 1999
Verevkin, Sergey P., Thermochemistry of phenols: buttress effects in sterically hindered phenols, The Journal of Chemical Thermodynamics, 1999, 31, 11, 1397-1416, https://doi.org/10.1006/jcht.1999.0466 . [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]

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]

Chickos, Braton, et al., 1991, 2
Chickos, James S.; Braton, C. Marie; Hesse, Donald G.; Liebman, Joel F., Estimating entropies and enthalpies of fusion of organic compounds, J. Org. Chem., 1991, 56, 3, 927-938, https://doi.org/10.1021/jo00003a007 . [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]

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]


Notes

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