Phenol, 2-(1,1-dimethylethyl)-

• Formula: C₁₀H₁₄O
• Molecular weight: 150.2176
• IUPAC Standard InChI: InChI=1S/C10H14O/c1-10(2,3)8-6-4-5-7-9(8)11/h4-7,11H,1-3H3 Copy

  
• IUPAC Standard InChIKey: WJQOZHYUIDYNHM-UHFFFAOYSA-N Copy
• CAS Registry Number: 88-18-6
• 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.
• Other names: Phenol, o-tert-butyl-; o-tert-Butylphenol; 2-tert-Butylphenol; 2-t-Butylphenol; Phenol, 2-tert-butyl-; 2-(1,1-Dimethylethyl)-phenol
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• Information on this page:
  • 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)
  • Gas Chromatography
  • References
  • Notes
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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

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

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.

Enthalpy of vaporization

Antoine Equation Parameters

log₁₀(P) = A − (B / (T + C))
    P = vapor pressure (atm)
    T = temperature (K)

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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^- +  =

By formula: C₁₀H₁₃O^- + H⁺ = C₁₀H₁₄O

 +  =  + 

By formula: C₁₈H₃₀O + C₁₀H₁₄O = C₁₄H₂₂O + C₁₄H₂₂O

 +  =  + 

By formula: C₆H₆O + C₁₄H₂₂O = C₁₀H₁₄O + C₁₀H₁₄O

 +  = 2

By formula: C₆H₆O + C₁₄H₂₂O = 2C₁₀H₁₄O

 +  =  + 

By formula: C₆H₆O + C₁₄H₂₂O = C₁₀H₁₄O + C₁₀H₁₄O

=

By formula: C₁₀H₁₄O = C₁₀H₁₄O

=

By formula: C₁₀H₁₄O = C₁₀H₁₄O

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
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

Ionization energy determinations

De-protonation reactions

C₁₀H₁₃O^- +  =

By formula: C₁₀H₁₃O^- + H⁺ = C₁₀H₁₄O

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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Additional Data

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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Additional Data

Gas Chromatography

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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

Kovats' RI, non-polar column, isothermal

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Van Den Dool and Kratz RI, non-polar column, temperature ramp

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Van Den Dool and Kratz RI, non-polar column, custom temperature program

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Normal alkane RI, non-polar column, temperature ramp

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Normal alkane RI, non-polar column, custom temperature program

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Normal alkane RI, polar column, custom temperature program

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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), Gas Chromatography, NIST Free Links, NIST Subscription Links, 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]

Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc., Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]

Tsvetkov, Nazmutdinov, et al., 1986
Tsvetkov, V.S.; Nazmutdinov, A.G.; Sharonov, K.S.; Rozhnov, A.M., Termodin. Org. Soedin., 1986, 71. [all data]

McDonald, Shrader, et al., 1959
McDonald, R.A.; Shrader, S.A.; Stull, D.R., Vapor Pressures and Freezing Points of 30 Organics, J. Chem. Eng. Data, 1959, 4, 311. [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]

Nesterova, Nazmutdinov, et al., 1990
Nesterova, T.N.; Nazmutdinov, A.G.; Tsvetkov, V.S.; Rozhnov, A.M.; Roshchupkina, I. Yu, Vapour pressures and enthalpies of vaporization of alkylphenols, The Journal of Chemical Thermodynamics, 1990, 22, 4, 365-377, https://doi.org/10.1016/0021-9614(90)90122-7 . [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]

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

McDonald, Shrader, et al., 1959, 2
McDonald, R.A.; Shrader, S.A.; Stull, D.R., Vapor Pressures and Freezing Points of Thirty Pure Organic Compounds., J. Chem. Eng. Data, 1959, 4, 4, 311-313, https://doi.org/10.1021/je60004a009 . [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]

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]

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]

Engewald, Billing, et al., 1988
Engewald, W.; Billing, U.; Topalova, I.; Petsev, N., Structure-retention correlations of alkylphenols in gas-liquid and gas-solid chromatography, J. Chromatogr., 1988, 446, 71-77, https://doi.org/10.1016/S0021-9673(00)94419-4 . [all data]

Gautzsch and Zinn, 1996
Gautzsch, R.; Zinn, P., Use of incremental models to estimate the retention indexes of aromatic compounds, Chromatographia, 1996, 43, 3/4, 163-176, https://doi.org/10.1007/BF02292946 . [all data]

Mjøs, Meier, et al., 2006
Mjøs, S.A.; Meier, S.; Boitsov, S., Alkylphenol retention indices, J. Chromatogr. A, 2006, 1123, 1, 98-105, https://doi.org/10.1016/j.chroma.2006.05.002 . [all data]

Okumura, 1991
Okumura, T., retention indices of environmental chemicals on methyl silicone capillary column, Journal of Environmental Chemistry (Japan), 1991, 1, 2, 333-358, https://doi.org/10.5985/jec.1.333 . [all data]

Peng, 1996
Peng, C.T., Gas chromatographic identification of aromatic hydrocarbons in Liquid Scintillation Spectrometry, Cook, G.T.; Harkness, D.D.; MacKenzie, A.B.; Miller, B.F.; Scott, E.M., ed(s)., 1996, 221-232. [all data]

Peng, Yang, et al., 1991
Peng, C.T.; Yang, Z.C.; Ding, S.F., Prediction of rentention idexes. II. Structure-retention index relationship on polar columns, J. Chromatogr., 1991, 586, 1, 85-112, https://doi.org/10.1016/0021-9673(91)80028-F . [all data]

Notes

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• Symbols used in this document:
  

  Tboil	Boiling point
  Tfus	Fusion (melting) point
  ΔcH°liquid	Enthalpy of combustion of liquid at standard conditions
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔfH°liquid	Enthalpy of formation of liquid at standard conditions
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction 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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