Benzoic acid, p-tert-butyl-
- Formula: C11H14O2
- Molecular weight: 178.2277
- IUPAC Standard InChI: InChI=1S/C11H14O2/c1-11(2,3)9-6-4-8(5-7-9)10(12)13/h4-7H,1-3H3,(H,12,13)
- IUPAC Standard InChIKey: KDVYCTOWXSLNNI-UHFFFAOYSA-N
- CAS Registry Number: 98-73-7
- 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: Benzoic acid, 4-(1,1-dimethylethyl)-; p-tert-Butylbenzoic acid; 4-tert-Butylbenzoic acid; 4-t-Butylbenzoic acid; p-t-Butylbenzoic acid; TBBA; Kyselina p-terc.butylbenzoova; NSC 4802; 4-(1,1-Dimethylethyl)benzoic acid
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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 | -398.5 ± 2.0 | kJ/mol | Ccb | Colomina, Jimenez, et al., 1979 |
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
C11H13O2- + =
By formula: C11H13O2- + H+ = C11H14O2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 1423. ± 9.2 | kJ/mol | G+TS | Kulhanek, Decouzon, et al., 1999 | gas phase |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 1393. ± 8.4 | kJ/mol | IMRE | Kulhanek, Decouzon, et al., 1999 | 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
LL - Sharon G. Lias and Joel F. Liebman
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 |
|---|---|---|---|
| 8.94 | PI | Takhistov, Misharev, et al., 1995 | LL |
| 8.94 ± 0.02 | EI | Orlov, Misharev, et al., 1986 | LBLHLM |
Appearance energy determinations
| Ion | AE (eV) | Other Products | Method | Reference | Comment |
|---|---|---|---|---|---|
| C10H11O2+ | 9.62 | CH3 | PI | Takhistov, Misharev, et al., 1995 | LL |
| C10H11O2+ | 9.8 ± 0.1 | CH3 | EI | Orlov, Misharev, et al., 1986 | LBLHLM |
| C11H13O+[(CH3)3CC6H4CO+] | 9.59 | OH | EST | Takhistov, Misharev, et al., 1995 | LL |
De-protonation reactions
C11H13O2- + =
By formula: C11H13O2- + H+ = C11H14O2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 1423. ± 9.2 | kJ/mol | G+TS | Kulhanek, Decouzon, et al., 1999 | gas phase; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 1393. ± 8.4 | kJ/mol | IMRE | Kulhanek, Decouzon, et al., 1999 | gas phase; B |
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
Van Den Dool and Kratz RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Packed | SE-30 | 1486. | Peng, Ding, et al., 1988 | He, Supelcoport and Chromosorb, 40. C @ 4. min, 10. K/min, 250. C @ 60. min; Column length: 3.05 m |
Normal alkane RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | Ultra-1 | 1472. | Okumura, 1991 | 25. m/0.32 mm/0.25 μm, He, 3. K/min; Tstart: 80. C; Tend: 260. C |
References
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Colomina, Jimenez, et al., 1979
Colomina, M.; Jimenez, P.; Perez-Ossorio, R.; Turrion, C.,
Thermochemical properties of benzoic acid derivatives. VIII. Enthalpies of combustion and formation of o-, m-, and p-t-butylbenzoic acids,
J. Chem. Thermodyn., 1979, 11, 1179-1184. [all data]
Kulhanek, Decouzon, et al., 1999
Kulhanek, J.; Decouzon, M.; Gal, J.F.; Maria, P.C.; Fiedler, P.; Jimenez, P.; Roux, M.V.; Exner, O.,
Steric effects and steric hindrance to resonance in tert-butylbenzoic acids in the gas phase and in solution,
Eur. J. Org., 1999, Chem., 7, 1589-1594, https://doi.org/10.1002/(SICI)1099-0690(199907)1999:7<1589::AID-EJOC1589>3.0.CO;2-S
. [all data]
Takhistov, Misharev, et al., 1995
Takhistov, V.V.; Misharev, A.D.; Orlov, V.M.; Ponomarev, D.A.; Voss, J.,
Thermochemistry and mass spectrometry of aromatic compounds with tertiary alkyl groups,
Eur. Mass Spectrom., 1995, 1, 353. [all data]
Orlov, Misharev, et al., 1986
Orlov, V.; Misharev, A.; Takhistox, V.,
Determination of the enthalpy of formation of para-substituted α,α-dimethyl cations in the gas phase,
Izv. Akad. Nauk SSSR Ser. Khim., 1986, 9, 2006. [all data]
Peng, Ding, et al., 1988
Peng, C.T.; Ding, S.F.; Hua, R.L.; Yang, Z.C.,
Prediction of Retention Indexes I. Structure-Retention Index Relationship on Apolar Columns,
J. Chromatogr., 1988, 436, 137-172, https://doi.org/10.1016/S0021-9673(00)94575-8
. [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]
Notes
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Gas Chromatography, 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 - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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