Phenol, p-tert-butyl-
- Formula: C10H14O
- Molecular weight: 150.2176
- IUPAC Standard InChI: InChI=1S/C10H14O/c1-10(2,3)8-4-6-9(11)7-5-8/h4-7,11H,1-3H3
- IUPAC Standard InChIKey: QHPQWRBYOIRBIT-UHFFFAOYSA-N
- CAS Registry Number: 98-54-4
- 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, 4-(1,1-dimethylethyl)-; p-tert-Butylphenol; Butylphen; 4-tert-Butylphenol; 4-t-Butylphenol; 4-(1,1-Dimethylethyl)phenol; p-terc.Butylfenol; 1-Hydroxy-4-tert-butylbenzene; PTBP; Phenol, 4-tert-butyl-; p-t-Butylphenol; NSC 3697
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Gas phase thermochemistry data
Go To: Top, Gas phase ion energetics data, Gas Chromatography, 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 |
|---|---|---|---|---|---|
| ΔfH°gas | -44.50 | kcal/mol | Eqk | Verevkin, 1982 | Isomerization; ALS |
| ΔfH°gas | -51.34 | kcal/mol | N/A | Ammar, El Sayed, et al., 1977 | Value computed using ΔfHsolid° value of -310.5±1.2 kj/mol from Ammar, El Sayed, et al., 1977 and ΔsubH° value of 95.7 kj/mol from Bertholon, Giray, et al., 1971.; DRB |
| ΔfH°gas | -41.67 | kcal/mol | Ccb | Bertholon, Giray, et al., 1971 | ALS |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Gas Chromatography, 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
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 |
|---|---|---|---|
| 7.8 | PE | Cetinkaya, Lappert, et al., 1983 | LBLHLM |
| 8.16 | PE | Cetinkaya, Lappert, et al., 1983 | Vertical value; LBLHLM |
De-protonation reactions
C10H13O- + =
By formula: C10H13O- + H+ = C10H14O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 348.5 ± 2.1 | kcal/mol | G+TS | Fujio, McIver, et al., 1981 | gas phase; value altered from reference due to change in acidity scale; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 341.6 ± 2.0 | kcal/mol | IMRE | Fujio, McIver, et al., 1981 | gas phase; value altered from reference due to change in acidity scale; 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
Kovats' RI, non-polar column, isothermal
| Column type | Active phase | Temperature (C) | I | Reference | Comment |
|---|---|---|---|---|---|
| Capillary | PS-255 | 150. | 1274. | Engewald, Billing, et al., 1988 | 50. m/0.30 mm/0.25 μm |
Kovats' RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | SE-30 | 1256. | Medvedovskaya, Tikhomirova, et al., 1997 | 7. K/min; Tstart: 50. C; Tend: 320. C |
Van Den Dool and Kratz RI, non-polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | VF-5MS | 1294.7 | Mjøs, Meier, et al., 2006 | 50. m/0.25 mm/0.25 μm, He; Program: 60C(2min) => 30C/min => 100C => 1C/min => |
| Capillary | VF-5MS | 1295.6 | Mjøs, Meier, et al., 2006 | 50. m/0.25 mm/0.25 μm, He; Program: 60C(2min) => 30C/min => 100C => 2C/min => |
| Capillary | VF-5MS | 1297.8 | Mjøs, Meier, et al., 2006 | 50. m/0.25 mm/0.25 μm, He; Program: 60C(2min) => 30C/min => 100C => 4C/min => |
| Capillary | 5 % Phenyl methyl siloxane | 1297. | Yasuhara, Shiraishi, et al., 1997 | 25. m/0.31 mm/0.52 μm, He; Program: 50C(2min) => (20C/min) => 120C => (7C/min) => 310C(10min) |
Normal alkane RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | HP-5 MS | 1292. | Zenkevich, Makarov A.A., et al., 2009 | 30. m/0.25 mm/0.25 μm, Helium, 2. K/min, 220. C @ 10. min; Tstart: 50. C |
| Capillary | SPB-5 | 1291. | Poligné, Collignan, et al., 2001 | 60. m/0.32 mm/1. μm, He, 3. K/min; Tstart: 40. C; Tend: 200. C |
| Capillary | Ultra-1 | 1265. | Okumura, 1991 | 25. m/0.32 mm/0.25 μm, He, 3. K/min; Tstart: 80. C; Tend: 260. C |
Normal alkane RI, non-polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | CP Sil 5 CB | 1261. | Guyot, Bouseta, et al., 1998 | 50. m/0.32 mm/1.2 μm, He; Program: 30C => 55C/min => 85C => 1C/min => 145C => 3C/min => 250C |
References
Go To: Top, Gas phase 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.
Verevkin, 1982
Verevkin, S.P.,
Study of equilibrium of tert-butylphenol dealkylation in the gas phase,
Termodin. Organ. Soedin., 1982, 67-70. [all data]
Ammar, El Sayed, et al., 1977
Ammar, M.M.; El Sayed, N.; Morsi, S.E.; El Azmirly, A.,
The enthalpies of combustion and formation of p-tertiary butyl phenol and naphthalene,
Egypt. J. Phys., 1977, 8, 111-118. [all data]
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]
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]
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]
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]
Medvedovskaya, Tikhomirova, et al., 1997
Medvedovskaya, I.I.; Tikhomirova, S.V.; Krasavina, T.D.; Gubkina, L.N.,
Comparison of results of chromatographic identification of complex mixtures of organic compounds,
Proc. Omsk. Univ., 1997, 4, 34-36. [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]
Yasuhara, Shiraishi, et al., 1997
Yasuhara, A.; Shiraishi, H.; Nishikawa, M.; Yamamoto, T.; Uehiro, T.; Nakasugi, O.; Okumura, T.; Kenmotsu, K.; Fukui, H.; Nagase, M.; Ono, Y.; Kawagoshi, Y.; Baba, K.; Noma, Y.,
Determination of organic components in leachates from hazardous waste disposal sites in Japan by gas chromatography-mass spectrometry,
J. Chromatogr. A, 1997, 774, 1-2, 321-332, https://doi.org/10.1016/S0021-9673(97)00078-2
. [all data]
Zenkevich, Makarov A.A., et al., 2009
Zenkevich, I.G.; Makarov A.A.; Schrader, S.; Moeder, M.,
A new version of an additive scheme for the prediction of gas chromatographic retention indices of the 211 structural isomers of 4-nonylphenol,
J. Chromatogr. A, 2009, 1216, 18, 4097-4106, https://doi.org/10.1016/j.chroma.2009.03.021
. [all data]
Poligné, Collignan, et al., 2001
Poligné, I.; Collignan, A.; Trystram, G.,
Characterization of traditional processing of pork meat into boucané,
Meat Sci., 2001, 59, 4, 377-389, https://doi.org/10.1016/S0309-1740(01)00090-0
. [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]
Guyot, Bouseta, et al., 1998
Guyot, C.; Bouseta, A.; Scheirman, V.; Collin, S.,
Floral origin markers of chestnut and lime tree honeys,
J. Agric. Food Chem., 1998, 46, 2, 625-633, https://doi.org/10.1021/jf970510l
. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, Gas Chromatography, References
- Symbols used in this document:
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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