tert-Butyl Hydroperoxide

• Formula: C₄H₁₀O₂
• Molecular weight: 90.1210
• IUPAC Standard InChI: InChI=1S/C4H10O2/c1-4(2,3)6-5/h5H,1-3H3 Copy

  
• IUPAC Standard InChIKey: CIHOLLKRGTVIJN-UHFFFAOYSA-N Copy
• CAS Registry Number: 75-91-2
• Chemical structure:
  This structure is also available as a 2d Mol file
• Other names: Hydroperoxide, 1,1-dimethylethyl; Cadox TBH; Perbutyl H; 2-Hydroperoxy-2-methylpropane; 1,1-Dimethylethyl hydroperoxide; tert-C4H9OOH; tert-Butyl hydrogen peroxide; Hydroperoxide, tert-butyl; Hydroperoxyde de butyle tertiaire; Slimicide DE-488; Terc. butylhydroperoxid; Trigonox A-75; TBHP-70; Trigonox A-W70; t-Butylhydroperoxide; Aztec t-butyl Hydroperoxide-70, Aq; Dimethylethyl hydroperoxide; T-Hydro; TBHP; Tertiary-butyl hydroperoxide; NSC 672
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• Information on this page:
  • Gas phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • Mass spectrum (electron ionization)
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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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

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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.

Enthalpy of vaporization

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: John E. Bartmess

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

C₄H₉O₂^- +  =

By formula: C₄H₉O₂^- + H⁺ = C₄H₁₀O₂

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
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
LL - Sharon G. Lias and Joel F. Liebman

Ionization energy determinations

Appearance energy determinations

De-protonation reactions

C₄H₉O₂^- +  =

By formula: C₄H₉O₂^- + H⁺ = C₄H₁₀O₂

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

References

Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, 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.

Khursan and Martem'yanov, 1991
Khursan, S.L.; Martem'yanov, V.S., Thermochemistry of the recombination of peroxyl radicals, Russ. J. Phys. Chem. (Engl. Transl.), 1991, 65, 321-325. [all data]

Kozlov and Rabinovich, 1964
Kozlov, N.A.; Rabinovich, I.B., Thermodynamics of isopropylbenzene and tert-butyl hydroperoxides. I. Heat of combustion and the formation of hydroperoxides; [bond] energy of oxygen-oxygen bond, Tr. Khim. Khim. Tekhnol., 1964, 189-193. [all data]

Vaughan, 1951
Vaughan, W.E., General discussion (communicated), Discuss. Faraday Soc., 1951, 10, 330. [all data]

Egerton, Emte, et al., 1951
Egerton, A.C.; Emte, W.; Minkoff, G.J., Some properties of organic peroxides, Faraday Discuss. Chem. Soc., 1951, 10, 278. [all data]

Clifford, Wenthold, et al., 1998
Clifford, E.P.; Wenthold, P.G.; Gareyev, R.; Lineberger, W.C.; DePuy, C.H.; Bierbaum, V.M.; Ellison, G.B., Photoelectron spectroscopy, gas phase acidity, and thermochemistry of tert-butyl hydroperoxide: Mechanisms for the rearrangement of peroxyl radicals, J. Chem. Phys., 1998, 109, 23, 10293-10310, https://doi.org/10.1063/1.477725 . [all data]

Batich and Adam, 1974
Batich, C.; Adam, W., The photoelectron spectra of alkylperoxides, Tetrahedron Lett., 1974, 1467. [all data]

Holmes, Lossing, et al., 1991
Holmes, J.L.; Lossing, F.P.; Mayer, P.M., Heats of formation of oxygen-containing organic free radicals from appearance energy measurements, J. Am. Chem. Soc., 1991, 113, 9723. [all data]

Notes

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

• Symbols used in this document:
  

  AE	Appearance energy
  ΔfH°gas	Enthalpy of formation of gas 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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