tert-Butyl Hydroperoxide
- Formula: C4H10O2
- Molecular weight: 90.1210
- IUPAC Standard InChI: InChI=1S/C4H10O2/c1-4(2,3)6-5/h5H,1-3H3
- IUPAC Standard InChIKey: CIHOLLKRGTVIJN-UHFFFAOYSA-N
- 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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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 |
|---|---|---|---|---|---|
| ΔfH°gas | -234.9 | kJ/mol | Eqk | Khursan and Martem'yanov, 1991 | hf from V. P.Komissarov's report |
| ΔfH°gas | -246. ± 5.0 | kJ/mol | Ccb | Kozlov and Rabinovich, 1964 |
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 |
|---|---|---|---|---|---|
| ΔfH°liquid | -294. ± 5.0 | kJ/mol | Ccb | Kozlov and Rabinovich, 1964 | |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -2710. ± 5.0 | kJ/mol | Ccb | Kozlov and Rabinovich, 1964 | Corresponding ΔfHºliquid = -294. kJ/mol (simple calculation by NIST; no Washburn corrections) |
| ΔcH°liquid | -2737. | kJ/mol | Ccb | Vaughan, 1951 | Corresponding ΔfHºliquid = -266. kJ/mol (simple calculation by NIST; no Washburn corrections) |
| ΔcH°liquid | -2736. ± 1. | kJ/mol | Ccb | Bell, Dickey, et al., 1949 | Corresponding ΔfHºliquid = -267. 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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔvapH° | 47.7 ± 0.2 | kJ/mol | V | Kozlov and Rabinovich, 1964 | ALS |
| ΔvapH° | 48.0 | kJ/mol | N/A | Kozlov and Rabinovich, 1964 | DRB |
| ΔvapH° | 48.1 | kJ/mol | V | Vaughan, 1951 | ALS |
Enthalpy of vaporization
| ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 46.568 | 153. | V | Egerton, Emte, et al., 1951 | ALS |
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
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 1552. ± 8.8 | kJ/mol | G+TS | Clifford, Wenthold, et al., 1998 | gas phase |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 1520. ± 8.4 | kJ/mol | IMRE | Clifford, Wenthold, et al., 1998 | gas 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:
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
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 10.24 | PE | Batich and Adam, 1974 | Vertical value; LLK |
Appearance energy determinations
| Ion | AE (eV) | Other Products | Method | Reference | Comment |
|---|---|---|---|---|---|
| HO2+ | 9.90 | C4H9 | EI | Holmes, Lossing, et al., 1991 | LL |
De-protonation reactions
C4H9O2- + =
By formula: C4H9O2- + H+ = C4H10O2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 1552. ± 8.8 | kJ/mol | G+TS | Clifford, Wenthold, et al., 1998 | gas phase; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 1520. ± 8.4 | kJ/mol | IMRE | Clifford, Wenthold, et al., 1998 | gas phase; B |
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
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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 | NIST Mass Spectrometry Data Center |
| NIST MS number | 341918 |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), NIST Free Links, 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]
Bell, Dickey, et al., 1949
Bell, E.R.; Dickey, F.H.; Raley, J.H.; Rust, F.F.; Vaughan, W.E.,
Oxidation of branched-chain compounds,
Ind. Eng. Chem., 1949, 41, 2597-2604. [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
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- Symbols used in this document:
AE Appearance energy 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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