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Phenol, p-tert-butyl-

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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 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
Deltafgas-186.2kJ/molEqkVerevkin, 1982Isomerization; ALS
Deltafgas-214.8kJ/molN/AAmmar, El Sayed, et al., 1977Value computed using «DELTA»fHsolid° value of -310.5±1.2 kj/mol from Ammar, El Sayed, et al., 1977 and «DELTA»subH° value of 95.7 kj/mol from Bertholon, Giray, et al., 1971.; DRB
Deltafgas-174.3kJ/molCcbBertholon, Giray, et al., 1971ALS

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
Deltafsolid-310.5 ± 1.2kJ/molCcbAmmar, El Sayed, et al., 1977 
Deltafsolid-270.kJ/molCcbBertholon, Giray, et al., 1971 
Quantity Value Units Method Reference Comment
Deltacsolid-5625.8 ± 1.2kJ/molCcbAmmar, El Sayed, et al., 1977Corresponding «DELTA»fsolid = -310.1 kJ/mol (simple calculation by NIST; no Washburn corrections)
Deltacsolid-5669.kJ/molCcbBertholon, Giray, et al., 1971Corresponding «DELTA»fsolid = -270. 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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny, 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
Tboil507. ± 10.KAVGN/AAverage of 11 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus372. ± 2.KAVGN/AAverage of 32 out of 33 values; Individual data points
Quantity Value Units Method Reference Comment
Deltavap67.9 ± 1.0kJ/molCRibeiro da Silva, Matos, et al., 1999AC
Quantity Value Units Method Reference Comment
Deltasub89.4 ± 2.5kJ/molCRibeiro da Silva, Matos, et al., 1999AC
Deltasub85.9 ± 0.5kJ/molGSVerevkin, 1999Based on data from 293. - 334. K.; AC
Deltasub93.43kJ/molCBertholon, Giray, et al., 1971ALS
Deltasub95.7kJ/molN/ABertholon, Giray, et al., 1971DRB

Enthalpy of vaporization

DeltavapH (kJ/mol) Temperature (K) Method Reference Comment
54.3486.A,GS,EBStephenson and Malanowski, 1987Based on data from 471. - 525. K. See also Stull, 1947 and Handley, Harrop, et al., 1964.; AC
59.6348.N/AStage, Müller, et al., 1953Based on data from 346. - 523. K.; AC
57.6373.N/AStage, Müller, et al., 1953Based on data from 346. - 523. K.; AC
56.6398.N/AStage, Müller, et al., 1953Based on data from 346. - 523. K.; AC
54.4423.N/AStage, Müller, et al., 1953Based on data from 346. - 523. K.; AC
49.9473.N/AStage, Müller, et al., 1953Based on data from 346. - 523. K.; AC

Antoine Equation Parameters

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

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Temperature (K) A B C Reference Comment
471.27 - 524.84.118251622.037-118.559Handley, Harrop, et al., 1964, 2Coefficents calculated by NIST from author's data.

Enthalpy of sublimation

DeltasubH (kJ/mol) Temperature (K) Method Reference Comment
85.0 ± 0.5313.GSVerevkin, 1999Based on data from 293. - 334. K.; AC
84.3292.AStephenson and Malanowski, 1987Based on data from 280. - 304. K. See also Aihara, 1960.; AC

Enthalpy of fusion

DeltafusH (kJ/mol) Temperature (K) Reference Comment
14.52373.2Inozemtsev, Liakumovich, et al., 1972AC

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

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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
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

C10H13O- + Hydrogen cation = Phenol, p-tert-butyl-

By formula: C10H13O- + H+ = C10H14O

Quantity Value Units Method Reference Comment
Deltar1458. ± 8.8kJ/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Deltar1429. ± 8.4kJ/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B

Phenol, p-tert-butyl- = Phenol, m-tert-butyl-

By formula: C10H14O = C10H14O

Quantity Value Units Method Reference Comment
Deltar-1.0kJ/molEqkVerevkin, 1982gas phase; Isomerization; ALS
Deltar-1. ± 1.3kJ/molEqkPil'shchikov, Nesterova, et al., 1981liquid phase; ALS

Phenol + Phenol, 3,5-bis(1,1-dimethylethyl)- = Phenol, m-tert-butyl- + Phenol, p-tert-butyl-

By formula: C6H6O + C14H22O = C10H14O + C10H14O

Quantity Value Units Method Reference Comment
Deltar0.08 ± 0.71kJ/molEqkPil'shchikov, Nesterova, et al., 1981liquid phase; ALS

Phenol + 2,4-Di-tert-butylphenol = Phenol, 2-(1,1-dimethylethyl)- + Phenol, p-tert-butyl-

By formula: C6H6O + C14H22O = C10H14O + C10H14O

Quantity Value Units Method Reference Comment
Deltar-0. ± 4.kJ/molEqkPil'shchikov, Nesterova, et al., 1981liquid phase; ALS

Phenol, 2,4,6-tri-tert-butyl- + Phenol, p-tert-butyl- = 22,4-Di-tert-butylphenol

By formula: C18H30O + C10H14O = 2C14H22O

Quantity Value Units Method Reference Comment
Deltar-12.4 ± 2.0kJ/molEqkPil'shchikov, Nesterova, et al., 1981liquid phase; ALS

Phenol, p-tert-butyl- = Phenol, 2-(1,1-dimethylethyl)-

By formula: C10H14O = C10H14O

Quantity Value Units Method Reference Comment
Deltar18.6 ± 0.79kJ/molEqkPil'shchikov, Nesterova, et al., 1981liquid phase; ALS

Phenol, 2-(1,1-dimethylethyl)- = Phenol, p-tert-butyl-

By formula: C10H14O = C10H14O

Quantity Value Units Method Reference Comment
Deltar-16.9 ± 1.6kJ/molEqkNesterova, Verevkin, et al., 1985liquid phase; ALS

Phenol, p-tert-butyl- = Phenol + 1-Propene, 2-methyl-

By formula: C10H14O = C6H6O + C4H8

Quantity Value Units Method Reference Comment
Deltar71.0 ± 2.1kJ/molEqkVerevkin, 1982gas phase; ALS

Henry's Law 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: Rolf Sander

Henry's Law constant (water solution)

kH(T) = H exp(d(ln(kH))/d(1/T) ((1/T) - 1/(298.15 K)))
H = Henry's law constant for solubility in water at 298.15 K (mol/kg*bar)
d(ln(kH))/d(1/T) = Temperature dependence constant (K)

H (mol/kg*bar) d(ln(kH))/d(1/T) (K) Method Reference Comment
890.7700.MN/AIt is assumed here that the thermodynamic data in missing citation refers to the units [mol/dm3] and [atm] as standard states.

Gas phase ion energetics data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, NIST Free Links, 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
7.8PECetinkaya, Lappert, et al., 1983LBLHLM
8.16PECetinkaya, Lappert, et al., 1983Vertical value; LBLHLM

De-protonation reactions

C10H13O- + Hydrogen cation = Phenol, p-tert-butyl-

By formula: C10H13O- + H+ = C10H14O

Quantity Value Units Method Reference Comment
Deltar1458. ± 8.8kJ/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Deltar1429. ± 8.4kJ/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B

IR Spectrum

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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

Gas Phase Spectrum

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IR spectrum
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Additional Data

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Owner NIST Standard Reference Data Program
Collection (C) 2018 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin Sadtler Research Labs Under US-EPA Contract
State gas

This IR spectrum is from the NIST/EPA Gas-Phase Infrared Database .


Mass spectrum (electron ionization)

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, IR Spectrum, UV/Visible spectrum, Gas Chromatography, NIST Free Links, 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

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Mass 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 Japan AIST/NIMC Database- Spectrum MS-NW-1815
NIST MS number 228357

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.


UV/Visible spectrum

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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: Victor Talrose, Eugeny B. Stern, Antonina A. Goncharova, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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UVVis spectrum
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Additional Data

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Source Coggeshall and Lang, 1948
Owner INEP CP RAS, NIST OSRD
Collection (C) 2007 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS
Source reference RAS UV No. 569
Instrument Beckman Spectrophotometer
Melting point 98
Boiling point 237

Gas Chromatography

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, NIST Free Links, 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

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Column type Active phase Temperature (C) I Reference Comment
CapillaryPS-255150.1274.Engewald, Billing, et al., 198850. m/0.30 mm/0.25 «mu»m

Kovats' RI, non-polar column, temperature ramp

View large format table.

Column type Active phase I Reference Comment
CapillarySE-301256.Medvedovskaya, Tikhomirova, et al., 19977. K/min; Tstart: 50. C; Tend: 320. C

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

View large format table.

Column type Active phase I Reference Comment
CapillaryVF-5MS1294.7Mjøs, Meier, et al., 200650. m/0.25 mm/0.25 «mu»m, He; Program: 60C(2min) => 30C/min => 100C => 1C/min =>
CapillaryVF-5MS1295.6Mjøs, Meier, et al., 200650. m/0.25 mm/0.25 «mu»m, He; Program: 60C(2min) => 30C/min => 100C => 2C/min =>
CapillaryVF-5MS1297.8Mjøs, Meier, et al., 200650. m/0.25 mm/0.25 «mu»m, He; Program: 60C(2min) => 30C/min => 100C => 4C/min =>
Capillary5 % Phenyl methyl siloxane1297.Yasuhara, Shiraishi, et al., 199725. m/0.31 mm/0.52 «mu»m, He; Program: 50C(2min) => (20C/min) => 120C => (7C/min) => 310C(10min)

Normal alkane RI, non-polar column, temperature ramp

View large format table.

Column type Active phase I Reference Comment
CapillaryHP-5 MS1292.Zenkevich, Makarov A.A., et al., 200930. m/0.25 mm/0.25 «mu»m, Helium, 2. K/min, 220. C @ 10. min; Tstart: 50. C
CapillarySPB-51291.Poligné, Collignan, et al., 200160. m/0.32 mm/1. «mu»m, He, 3. K/min; Tstart: 40. C; Tend: 200. C
CapillaryUltra-11265.Okumura, 199125. m/0.32 mm/0.25 «mu»m, He, 3. K/min; Tstart: 80. C; Tend: 260. C

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

View large format table.

Column type Active phase I Reference Comment
CapillaryCP Sil 5 CB1261.Guyot, Bouseta, et al., 199850. m/0.32 mm/1.2 «mu»m, He; Program: 30C => 55C/min => 85C => 1C/min => 145C => 3C/min => 250C

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, NIST Free Links, 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]

Ribeiro da Silva, Matos, et al., 1999
Ribeiro da Silva, M.A.V.; Matos, M.A.R.; Morais, V.M.F.; Miranda, M.S., Thermochemical and Theoretical Study of tert -Butyl and Di- tert -butylphenol Isomers, J. Org. Chem., 1999, 64, 24, 8816-8820, https://doi.org/10.1021/jo990801o . [all data]

Verevkin, 1999
Verevkin, S.P., Thermochemistry of phenols: quantification of theortho-,para-, andmeta-interactions in tert-alkyl substituted phenols, The Journal of Chemical Thermodynamics, 1999, 31, 5, 559-585, https://doi.org/10.1006/jcht.1998.0459 . [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]

Stull, 1947
Stull, Daniel R., Vapor Pressure of Pure Substances. Organic and Inorganic Compounds, Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022 . [all data]

Handley, Harrop, et al., 1964
Handley, R.; Harrop, D.; Martin, J.F.; Sprake, C.H.S., 846. Thermodynamic properties of organic oxygen compounds. Part XIV. Purification and vapour pressures of some alkylphenols, J. Chem. Soc., 1964, 4404, https://doi.org/10.1039/jr9640004404 . [all data]

Stage, Müller, et al., 1953
Stage, H.; Müller, E.; Faldix, P., Erdol u Kohle, 1953, 6, 375. [all data]

Handley, Harrop, et al., 1964, 2
Handley, R.; Harrop, D.; Martin, J.F.; Sprake, C.H.S., Thermodynamic Properties of Organic Oxygen Compounds. Part XIV. Purification and Vapour Pressures of Some Alkylphenols, J. Chem. Soc., 1964, 4404-4406, https://doi.org/10.1039/jr9640004404 . [all data]

Aihara, 1960
Aihara, Ariyuki, Estimation of the Energy of Hydrogen Bonds Formed in Crystals. II. Phenols, Bull. Chem. Soc. Jpn., 1960, 33, 2, 194-200, https://doi.org/10.1246/bcsj.33.194 . [all data]

Inozemtsev, Liakumovich, et al., 1972
Inozemtsev, P.P.; Liakumovich, A.G.; Gracheva, Z.D., Russ. J. Phys. Chem., 1972, 46, 6, 914. [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]

Pil'shchikov, Nesterova, et al., 1981
Pil'shchikov, V.A.; Nesterova, T.N.; Rozhnov, A.M., Equilibrium in the system phenol-tert-butylphenols, J. Appl. Chem. USSR, 1981, 54, 1765-1769. [all data]

Nesterova, Verevkin, et al., 1985
Nesterova, T.N.; Verevkin, S.P.; Malova, T.N.; Pilshchikov, V.A., Study of an equilibrium of tert-alkylphenols (thermodynamic analysis of the alkylation of phenols by branched olefins), Zh. Prikl. Khim. (Leningrad), 1985, 58, 827-833. [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]

Coggeshall and Lang, 1948
Coggeshall, N.D.; Lang, E.M., Influence of solvent, hydrogen bonding, temperature and conjugation on the ultraviolet spectra of phenols and aromatic hydrocarbons, J. Am. Chem. Soc., 1948, 70, 3283-3292. [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, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, NIST Free Links, References