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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Phase change data
Go To: Top, Gas phase ion energetics data, References, Notes
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° | 11.41 ± 0.04 | kcal/mol | V | Kozlov and Rabinovich, 1964 | ALS |
| ΔvapH° | 11.5 | kcal/mol | N/A | Kozlov and Rabinovich, 1964 | DRB |
| ΔvapH° | 11.5 | kcal/mol | V | Vaughan, 1951 | ALS |
Enthalpy of vaporization
| ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 11.130 | 153. | V | Egerton, Emte, et al., 1951 | ALS |
Gas phase ion energetics data
Go To: Top, Phase change data, References, Notes
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° | 370.9 ± 2.1 | kcal/mol | G+TS | Clifford, Wenthold, et al., 1998 | gas phase; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 363.2 ± 2.0 | kcal/mol | IMRE | Clifford, Wenthold, et al., 1998 | gas phase; B |
References
Go To: Top, Phase change data, Gas phase ion energetics data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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]
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]
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]
Notes
Go To: Top, Phase change data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy 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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