Home Symbol which looks like a small house Up Solid circle with an upward pointer in it

p-Cumenol

Data at NIST subscription sites:

NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.


Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Deltafgas-175.3 ± 2.4kJ/molEqkNesterova, Pimerzin, et al., 1989Author was aware that data differs from previously reported values; Isomerization
Deltafgas-183.9kJ/molCcbBertholon, Giray, et al., 1971 

Condensed phase thermochemistry data

Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Deltafsolid-270.kJ/molCcbBertholon, Giray, et al., 1971 
Quantity Value Units Method Reference Comment
Deltacsolid-4983.kJ/molCcbBertholon, Giray, et al., 1971Corresponding «DELTA»fsolid = -270. kJ/mol (simple calculation by NIST; no Washburn corrections)
Deltacsolid-4977. ± 13.kJ/molCcbBertholon, 1967Corresponding «DELTA»fsolid = -280. kJ/mol (simple calculation by NIST; no Washburn corrections)

Phase change data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), 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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Kenneth Kroenlein director
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.

Quantity Value Units Method Reference Comment
Tboil500. ± 4.KAVGN/AAverage of 12 out of 13 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus334. ± 2.KAVGN/AAverage of 12 values; Individual data points
Quantity Value Units Method Reference Comment
Deltasub88.07kJ/molCBertholon, Giray, et al., 1971ALS
Deltasub86.1kJ/molN/ABertholon, Giray, et al., 1971DRB

Enthalpy of vaporization

DeltavapH (kJ/mol) Temperature (K) Method Reference Comment
63.7406.EBNesterova, Nazmutdinov, et al., 1990Based on data from 391. - 507. K.; AC
63.1395.AStephenson and Malanowski, 1987Based on data from 380. - 496. K.; AC

Antoine Equation Parameters

log10(P) = A − (B / (T + C))
    P = vapor pressure (bar)
    T = temperature (K)

View plot Requires a JavaScript / HTML 5 canvas capable browser.

Temperature (K) A B C Reference Comment
381.3 - 501.45.776832801.531-15.386von Terres, Gebert, et al., 1955Coefficents calculated by NIST from author's data.

Enthalpy of sublimation

DeltasubH (kJ/mol) Temperature (K) Method Reference Comment
56. ± 2.223.0 ± 0.5VBertholon, 1967ALS

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


Reaction thermochemistry data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), 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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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

C9H11O- + Hydrogen cation = p-Cumenol

By formula: C9H11O- + H+ = C9H12O

Quantity Value Units Method Reference Comment
Deltar1461. ± 8.8kJ/molG+TSFujio, McIver, et al., 1981gas phase; «DELTA»Hf(AH) disagrees with group additivity by 8.6 kcal/mol (-41.4 kcal/mol; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Deltar1433. ± 8.4kJ/molIMREFujio, McIver, et al., 1981gas phase; «DELTA»Hf(AH) disagrees with group additivity by 8.6 kcal/mol (-41.4 kcal/mol; value altered from reference due to change in acidity scale; B

Phenol + Phenol, 2,4-bis(1-methylethyl)- = Phenol, 2-(1-methylethyl)- + p-Cumenol

By formula: C6H6O + C12H18O = C9H12O + C9H12O

Quantity Value Units Method Reference Comment
Deltar-0.7 ± 1.0kJ/molEqkNesterova, Pimerzin, et al., 1989liquid phase; Isomerization; ALS
Deltar-0.7 ± 1.0kJ/molEqkNesterova, Pilyshchikov, et al., 1983liquid phase; GC; ALS

p-Cumenol = Phenol, 3-(1-methylethyl)-

By formula: C9H12O = C9H12O

Quantity Value Units Method Reference Comment
Deltar-1.42 ± 0.29kJ/molEqkNesterova, Pilyshchikov, et al., 1983liquid phase; GC; ALS

Phenol, 2-(1-methylethyl)- = p-Cumenol

By formula: C9H12O = C9H12O

Quantity Value Units Method Reference Comment
Deltar-7.95 ± 0.21kJ/molEqkNesterova, Pilyshchikov, et al., 1983liquid phase; GC; ALS

Gas phase ion energetics data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), 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 by: John E. Bartmess

View reactions leading to C9H12O+ (ion structure unspecified)

De-protonation reactions

C9H11O- + Hydrogen cation = p-Cumenol

By formula: C9H11O- + H+ = C9H12O

Quantity Value Units Method Reference Comment
Deltar1461. ± 8.8kJ/molG+TSFujio, McIver, et al., 1981gas phase; «DELTA»Hf(AH) disagrees with group additivity by 8.6 kcal/mol (-41.4 kcal/mol; value altered from reference due to change in acidity scale
Quantity Value Units Method Reference Comment
Deltar1433. ± 8.4kJ/molIMREFujio, McIver, et al., 1981gas phase; «DELTA»Hf(AH) disagrees with group additivity by 8.6 kcal/mol (-41.4 kcal/mol; value altered from reference due to change in acidity scale

IR Spectrum

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), Gas Chromatography, References, Notes

Data compiled by: Coblentz Society, Inc.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director


Mass spectrum (electron ionization)

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, 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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.

Mass spectrum
For Zoom
1.) Enter the desired X axis range (e.g., 100, 200)
2.) Check here for automatic Y scaling
3.) Press here to zoom

Additional Data

View image of digitized spectrum (can be printed in landscape orientation).

View spectrum image in SVG format.

Download spectrum in JCAMP-DX format.

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, 1998.
NIST MS number 291808

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


Gas Chromatography

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

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

View large format table.

Column type Active phase Temperature (C) I Reference Comment
CapillarySE-30100.1201.Berezkin, Popova, et al., 199730. m/0.25 mm/0.5 «mu»m, He
CapillaryPS-255150.1204.Engewald, Billing, et al., 198850. m/0.30 mm/0.25 «mu»m

Van Den Dool and Kratz RI, non-polar column, temperature ramp

View large format table.

Column type Active phase I Reference Comment
CapillaryHP-5MS1247.Saroglou, Dorizas, et al., 200630. m/0.25 mm/0.25 «mu»m, He, 60. C @ 5. min, 4. K/min; Tend: 280. C

Normal alkane RI, non-polar column, temperature ramp

View large format table.

Column type Active phase I Reference Comment
CapillaryHP-5 MS1221.Bozi, Czagany, et al., 200730. m/0.25 mm/0.25 «mu»m, Helium, 50. C @ 1. min, 10. K/min, 300. C @ 4. min

Normal alkane RI, non-polar column, custom temperature program

View large format table.

Column type Active phase I Reference Comment
CapillarySLB-5 MS1227.Costa, De Fina, et al., 200830. m/0.25 mm/0.25 «mu»m, Helium; Program: 50 0C 3 0C/min -> 250 0C (1 min) 10 0C/min -> 300 0C (5 min)
CapillarySLB-5 MS1227.Costa, De Fina, et al., 200830. m/0.25 mm/0.25 «mu»m, Helium; Program: not specified
CapillaryCP Sil 5 CB1203.Weyerstahl, Marschall, et al., 1999Column length: 25. m; Column diameter: 0.39 mm; Program: not specified

Normal alkane RI, polar column, temperature ramp

View large format table.

Column type Active phase I Reference Comment
CapillaryDB-FFAP2227.Czerny, Brueckner, et al., 201130. m/0.32 mm/0.25 «mu»m, Helium, 40. C @ 2. min, 8. K/min, 230. C @ 5. min
CapillaryInnowax2241.Suleimenov, Atazharova, et al., 2003He, 60. C @ 10. min, 4. K/min, 220. C @ 10. min; Column length: 60. m; Column diameter: 0.25 mm

Normal alkane RI, polar column, custom temperature program

View large format table.

Column type Active phase I Reference Comment
CapillaryInnowax FSC2241.Baser, Demirci, et al., 200960. m/0.25 mm/0.25 «mu»m, Helium; Program: 60 0C (10 min) 4 0C/min -> 220 0C (10 min) 1 0C/min -> 240 0C
CapillaryInnowax2241.Tunaher, Kirimer, et al., 200360. m/0.25 mm/0.25 «mu»m, He; Program: 60C(10min) => 4C/min => 220C(10min) => 1C/min => 240C (20min)
CapillaryHP-Innowax FSC2241.Hüsnü Can Baser, Demirci, et al., 200260. m/0.25 mm/0.25 «mu»m, N2; Program: 60C(10min) => 4C/min => 220C(10min) => 1C/min => 240C
CapillaryHP-Innowax2241.Gören, Demirci, et al., 200160. m/0.25 mm/0.25 «mu»m, He; Program: 60 0C (10 min) 4 K/min -> 220 0C (10 min) 1 K/min -> 240 0C
CapillaryInnowax2241.Özcan, Akgül, et al., 200160. m/0.25 mm/0.25 «mu»m, He; Program: 60C(10min) => 4C/min => 200C(10min) => 1C/min => 240C
CapillaryInnowax2243.Baser, Özek, et al., 200060. m/0.25 mm/0.25 «mu»m, He; Program: 60 0C (10 min) 4 K/min -> 220 0C (10 min) 1 K/min -> 240 0C
CapillaryInnowax2242.Baser, Kürkcüoglu, et al., 199860. m/0.25 mm/0.25 «mu»m; Program: 60C(10min) => 4C/min => 220C(10min) => 1C/min => 240C

Lee's RI, non-polar column, temperature ramp

View large format table.

Column type Active phase I Reference Comment
CapillaryHP-5206.1Shao, Wang, et al., 200630. m/0.3 mm/0.25 «mu»m, He, 50. C @ 5. min, 5. K/min, 200. C @ 15. min

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Nesterova, Pimerzin, et al., 1989
Nesterova, T.N.; Pimerzin, A.A.; Rozhnov, A.M.; Karlina, T.N., Equilibria for the isomerization of (secondary-alkyl)phenols and cyclohexylphenols, J. Chem. Thermodyn., 1989, 21, 385-395. [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]

Bertholon, 1967
Bertholon, G., No. 534. - Etude physicochimique des phonols. VI. - Etude physicochimique des trois isopropylphenols isomeres, Bull. Soc. Chim. France, 1967, 8, 2977-2982. [all data]

Nesterova, Nazmutdinov, et al., 1990
Nesterova, T.N.; Nazmutdinov, A.G.; Tsvetkov, V.S.; Rozhnov, A.M.; Roshchupkina, I. Yu, Vapour pressures and enthalpies of vaporization of alkylphenols, The Journal of Chemical Thermodynamics, 1990, 22, 4, 365-377, https://doi.org/10.1016/0021-9614(90)90122-7 . [all data]

Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw, Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2 . [all data]

von Terres, Gebert, et al., 1955
von Terres, E.; Gebert, F.; Hulsemann, H.; Petereit, H.; Toepsch, H.; Ruppert, W., Zur Kenntnis der physikalisch-chemischen Grundlagen der Gewinnung und Zerlegung der Phenolfraktionen von Steinkohlenteer und Braunkohlenschwelteer. IV. Mitteilung Die Dampfdrucke von Phenol und Phenolderivaten, Brennst.-Chem., 1955, 36, 272-274. [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]

Nesterova, Pilyshchikov, et al., 1983
Nesterova, T.N.; Pilyshchikov, V.A.; Rozhnov, A.M., Chemical Equilibrium in the system isopropylphenols-phenol, J. Appl. Chem. USSR, 1983, 56, 1257-1261. [all data]

Berezkin, Popova, et al., 1997
Berezkin, V.G.; Popova, T.P.; Shiryayeva, V.Ye.; Nomura, N., Gas-chromatographic separation of monoalkylphenols on polar and non-polar phases by means of capillary chromatography, Pet. Chem. USSR (Engl. Transl.), 1997, 37, 2, 161-167. [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]

Saroglou, Dorizas, et al., 2006
Saroglou, V.; Dorizas, N.; Kypriotakis, Z.; Skaltsa, H.D., Analysis of the essential oil composition of eight Anthemis species from Greece, J. Chromatogr. A, 2006, 1104, 1-2, 313-322, https://doi.org/10.1016/j.chroma.2005.11.087 . [all data]

Bozi, Czagany, et al., 2007
Bozi, J.; Czagany, Z.; Meszaros, E.; Blazso, M., Thermal decomposition of flame retarded polycarbonates, J. Anal. Appl. Pyrolysis, 2007, 79, 1-2, 337-345, https://doi.org/10.1016/j.jaap.2007.01.001 . [all data]

Costa, De Fina, et al., 2008
Costa, R.; De Fina, M.R.; Valentino, M.R.; Rustaiyan, A.; Dugo, P.; Dugo, G.; Mondello, L., An investigation on the volatile composition of some Artemisia species from Iran, Flavour Fragr. J., 2008, 24, 2, 75-82, https://doi.org/10.1002/ffj.1919 . [all data]

Weyerstahl, Marschall, et al., 1999
Weyerstahl, P.; Marschall, H.; Splittgerber, U.; Son, P.T.; Giang, P.M.; Kaul, V.K., Constituents of the essential oil from the fruits of Zanthoxylum rhetsoides Drake from Vietnam and from the aerial parts of Zanthoxylum alatum Roxb. from India, Flavour Fragr. J., 1999, 14, 4, 225-229, https://doi.org/10.1002/(SICI)1099-1026(199907/08)14:4<225::AID-FFJ818>3.0.CO;2-1 . [all data]

Czerny, Brueckner, et al., 2011
Czerny, M.; Brueckner, R.; Kirchoff, E.; Schmitt, R.; Buettner, A., The influence of molecular structure on odor qualities and odor detection thresholds of volatile alkylated phenols, Chem. Senses, 2011, 1-15, retrieved from http://chemie.oxfordjournals.org. [all data]

Suleimenov, Atazharova, et al., 2003
Suleimenov, E.M.; Atazharova, G.A.; Demirchi, B.; Baser, K.H.C.; Adekenov, S.M., Essential oil composition of Artemisia Lercheana and A. Sieversiana of Kazakhstan flora in Recent problems of development of new medicines of natural origin, Proceedings of symposium, St.Petersburg - Pushkin, 2003, 382-385. [all data]

Baser, Demirci, et al., 2009
Baser, K.H.C.; Demirci, B.; Kurkcuoglu, M.; Satin, F.; Tumen, G., Comparative morphological and phytochemical charactertization of Salvia cadmica and S. smyrnaea, Pak. J. Bot., 2009, 41, 4, 1545-1555. [all data]

Tunaher, Kirimer, et al., 2003
Tunaher, Z.; Kirimer, N.; Baser, K.H.C., Wood essential oils of Juniperus foetidissima Willd., Holzforschung, 2003, 57, 140-144. [all data]

Hüsnü Can Baser, Demirci, et al., 2002
Hüsnü Can Baser, K.; Demirci, B.; Femirci, F.; Kocak, S.; Akinci, C.; Malyer, H.; Güleryüz, G., Composition and antimicrobial activity of the essential oil of Achellea multifida, Planta Medica, 2002, 68, 10, 941-943, https://doi.org/10.1055/s-2002-34923 . [all data]

Gören, Demirci, et al., 2001
Gören, N.; Demirci, B.; Baser, K.H.C., Composition of the essential oils of Tanacetum spp. from Turkey, Flavour Fragr. J., 2001, 16, 3, 191-194, https://doi.org/10.1002/ffj.976 . [all data]

Özcan, Akgül, et al., 2001
Özcan, M.; Akgül, A.; Bascr, K.H.C.; Özck, T.; Tabanca, N., Essential oil composition of sea fennel (Crithmum maritimum) form Turkey, Nahrung/Food, 2001, 45, 5, 353-356, https://doi.org/10.1002/1521-3803(20011001)45:5<353::AID-FOOD353>3.0.CO;2-4 . [all data]

Baser, Özek, et al., 2000
Baser, K.H.C.; Özek, T.; Demirci, B.; Duman, H., Composition of the essential oil of Glaucosciadium cordifolium (Boiss.) Burtt et Davis from Turkey, Flavour Fragr. J., 2000, 15, 1, 45-46, https://doi.org/10.1002/(SICI)1099-1026(200001/02)15:1<45::AID-FFJ867>3.0.CO;2-L . [all data]

Baser, Kürkcüoglu, et al., 1998
Baser, K.H.C.; Kürkcüoglu, M.; Aytac, Z., Composition of the essential oil of Salvia euphratica Montbret ex Bentham var. euphratica from Turkey, Flavour Fragr. J., 1998, 13, 1, 63-64, https://doi.org/10.1002/(SICI)1099-1026(199801/02)13:1<63::AID-FFJ694>3.0.CO;2-Z . [all data]

Shao, Wang, et al., 2006
Shao, X.; Wang, G.; Sun, Y.; Zhang, R.; Xie, K.; Liu, H., Determination and Characterization of the Pyrolysis Products of Isoprocarb by GC-MS, J. Chromatogr. Sci., 2006, 44, 3, 141-147, https://doi.org/10.1093/chromsci/44.3.141 . [all data]


Notes

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