p-Benzoquinone

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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
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Quantity Value Units Method Reference Comment
Δcgas-672. ± 1.kcal/molCcbWassermann, 1935Corresponding Δfgas = -29. kcal/mol (simple calculation by NIST; no Washburn corrections); ALS

Constant pressure heat capacity of gas

Cp,gas (cal/mol*K) Temperature (K) Reference Comment
9.00150.Becker E.D., 1965GT
11.39100.
14.63150.
18.29200.
23.82273.15
25.667298.15
25.801300.
32.579400.
38.176500.
42.665600.
46.264700.
49.187800.
51.592900.
53.5901000.
55.2651100.
56.6801200.
57.8851300.
58.9131400.
59.7941500.

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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Δfsolid-44.65 ± 0.17kcal/molCcbPilcher and Sutton, 1956ALS
Δfsolid-44.10 ± 0.15kcal/molCcbParks, Manchester, et al., 1954ALS
Δfsolid-44.09kcal/molCcbSchreiner, 1925ALS
Quantity Value Units Method Reference Comment
Δcsolid-651.482kcal/molCcbMagnus, 1956Corresponding Δfsolid = -49.455 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δcsolid-656.29 ± 0.10kcal/molCcbPilcher and Sutton, 1956Corresponding Δfsolid = -44.65 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δcsolid-656.84kcal/molCcbParks, Manchester, et al., 1954Corresponding Δfsolid = -44.10 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δcsolid-656.85kcal/molCcbSchreiner, 1925Corresponding Δfsolid = -44.09 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δcsolid-658.0kcal/molCcbSwietoslawski and Starczedska, 1925Corresponding Δfsolid = -42.9 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS

Constant pressure heat capacity of solid

Cp,solid (cal/mol*K) Temperature (K) Reference Comment
30.21298.15Ueberreiter and Orthmann, 1950T = 293 to 368 K. Equation only.; DH
31.60298.Andrews, Lynn, et al., 1926T = 22 to 160°C.; DH
31.00291.2Lange, 1924T = 22 to 291 K. Value is unsmoothed experimental datum.; DH

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:
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
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Tfus386.0KN/AAndrews, Lynn, et al., 1926, 2Uncertainty assigned by TRC = 0.3 K; TRC
Quantity Value Units Method Reference Comment
Δsub15.9 ± 0.38kcal/molDSCRojas-Aguilar, Flores-Lara, et al., 2004AC
Δsub15.0kcal/molCMagnus, 1956ALS
Δsub15.000kcal/molVCoolidge and Coolidge, 1927ALS

Enthalpy of vaporization

ΔvapH (kcal/mol) Temperature (K) Method Reference Comment
11.4395.AStephenson and Malanowski, 1987Based on data from 388. - 402. K.; AC

Enthalpy of sublimation

ΔsubH (kcal/mol) Temperature (K) Method Reference Comment
16.3 ± 0.1262.ME,TEde Kruif, 1981AC
15.0269.QFCoolidge and Coolidge, 1927Based on data from 260. - 278. K.; AC

Enthalpy of fusion

ΔfusH (kcal/mol) Temperature (K) Method Reference Comment
4.40 ± 0.02385.1DSCRojas-Aguilar, Flores-Lara, et al., 2004AC
4.39 ± 0.07385.7HFCRojas-Aguilar, Flores-Lara, et al., 2004AC
4.410388.N/AAcree, 1991AC
4.4097386.0N/AAndrews, Lynn, et al., 1926DH

Entropy of fusion

ΔfusS (cal/mol*K) Temperature (K) Reference Comment
11.4386.0Andrews, Lynn, et al., 1926DH

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:


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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
L - Sharon G. Lias

Data compiled as indicated in comments:
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
B - John E. Bartmess

Quantity Value Units Method Reference Comment
IE (evaluated)10.0 ± 0.1eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)191.0kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity183.9kcal/molN/AHunter and Lias, 1998HL

Electron affinity determinations

EA (eV) Method Reference Comment
1.850 ± 0.010LPESFu, Yang, et al., 2011Triplet state of neutral 2.32 eV up; B
1.8600 ± 0.0050LPESSchiedt and Weinkauf, 1999Neutral T1 state is 2.3 eV up: Siegert, Vogeler, et al., 20112; B
1.91 ± 0.10TDEqHeinis, Chowdhury, et al., 1988ΔGea(423 K) = -42.4 kcal/mol; ΔSea = -4.0 eu.; B
1.930 ± 0.048IMREFukuda and McIver, 1985ΔGea(355 K) = -43.1 kcal/mol; ΔSea =-4.0, est. from data in Heinis, Chowdhury, et al., 1988; B
1.990 ± 0.048LPDMarks, Comita, et al., 1985B
1.89 ± 0.30NBIECooper, Naff, et al., 1975B
1.370 ± 0.078SIFarragher and Page, 1966The Magnetron method, lacking mass analysis, is not considered reliable.; B

Ionization energy determinations

IE (eV) Method Reference Comment
10.11PELauer, Schafer, et al., 1975LLK
10.01PEKobayashi, 1975LLK
9.96 ± 0.01PIKotov and Potapov, 1972LLK
9.96 ± 0.01PIPotapov and Sorokin, 1971LLK
9.95PEDewar and Worley, 1969RDSH
9.7PITerenin, 1961RDSH
9.67 ± 0.02PIVilesov and Terenin, 1957RDSH
10.1PEBock, Mohmand, et al., 1983Vertical value; LBLHLM
9.99 ± 0.05PEDougherty and McGlynn, 1977Vertical value; LLK
10.03PECowan, Gleiter, et al., 1971Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C4H2O2+11.2 ± 0.05C2H2PIPotapov and Sorokin, 1971LLK
C5H4O+11.10 ± 0.05COPIPotapov and Sorokin, 1971LLK

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 NIST Mass Spectrometry Data Center
State gas
Instrument HP-GC/MS/IRD

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


Mass spectrum (electron ionization)

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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

Spectrum

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Mass spectrum
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Additional Data

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Due to licensing restrictions, this spectrum cannot be downloaded.

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-1277
NIST MS number 227766

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 missing citation
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. 558
Instrument Spectrophotometer SF-16
Melting point 115.7
Boiling point sub

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

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Column type Active phase Temperature (C) I Reference Comment
PackedSE-30180.905.Llobera and García-Raso, 1987N2, Chromosorb P AW DMCS; Column length: 2. m
PackedSE-30190.912.Llobera and García-Raso, 1987N2, Chromosorb P AW DMCS; Column length: 2. m
PackedSE-30200.919.Llobera and García-Raso, 1987N2, Chromosorb P AW DMCS; Column length: 2. m
PackedSE-30210.923.Llobera and García-Raso, 1987N2, Chromosorb P AW DMCS; Column length: 2. m

Kovats' RI, polar column, isothermal

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Column type Active phase Temperature (C) I Reference Comment
PackedCarbowax 20M180.1562.Llobera and García-Raso, 1987N2, Chromosorb P AW DMCS (60-80 mesh); Column length: 2. m
PackedCarbowax 20M190.1570.Llobera and García-Raso, 1987N2, Chromosorb P AW DMCS (60-80 mesh); Column length: 2. m
PackedCarbowax 20M200.1579.Llobera and García-Raso, 1987N2, Chromosorb P AW DMCS (60-80 mesh); Column length: 2. m
PackedCarbowax 20M210.1587.Llobera and García-Raso, 1987N2, Chromosorb P AW DMCS (60-80 mesh); Column length: 2. m

Normal alkane RI, non-polar column, temperature ramp

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Column type Active phase I Reference Comment
CapillaryOV-101888.Zenkevich, 200525. m/0.20 mm/0.10 μm, N2/He, 6. K/min; Tstart: 50. C; Tend: 250. C

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

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Column type Active phase I Reference Comment
CapillaryDB-5MS143.19Chen, Keeran, et al., 200230. m/0.25 mm/0.5 μm, 40. C @ 1. min, 10. K/min; Tend: 310. C
CapillaryDB-5MS147.33Chen, Keeran, et al., 200230. m/0.25 mm/0.5 μm, 40. C @ 1. min, 4. K/min; Tend: 310. C

References

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), 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.

Wassermann, 1935
Wassermann, A., The mechanism of additions to double bonds. Part I. Thermochemistry and kinetics of a diene synthesis, J. Chem. Soc., 1935, 828-838. [all data]

Becker E.D., 1965
Becker E.D., Molecular vibrations of quinones. VI. A vibrational assignment for p-benzoquinone and six isotopic derivatives. Thermodynamic functions of p-benzoquinone, J. Chem. Phys., 1965, 42, 942-949. [all data]

Pilcher and Sutton, 1956
Pilcher, G.; Sutton, L.E., The heats of combustion of quinol and p-benzoquinone and the thermodynamic quantities of the oxidation-reduction reaction, J. Chem. Soc., 1956, 2695-2700. [all data]

Parks, Manchester, et al., 1954
Parks, G.S.; Manchester, K.E.; Vaughan, L.M., Heats of combustion and formation of some alcohols, phenols, and ketones, J. Chem. Phys., 1954, 22, 2089-2090. [all data]

Schreiner, 1925
Schreiner, E., Thermodynamics of the quinhydrone electrode and the chemical constant of hydrogen, Z. Phys. Chem., 1925, 117, 57-87. [all data]

Magnus, 1956
Magnus, A., Die resonanzenergien der parachinone Aui grund der prazisionsmessungsen ihrer verbrennungswarmen durch herrn gerhard wittwer, Z. Phys. Chem. (Neue Folge), 1956, 9, 141-161. [all data]

Swietoslawski and Starczedska, 1925
Swietoslawski, W.; Starczedska, H., Correction des donnees thermochimiques de M.A. Valeur, J. Chem. Phys., 1925, 22, 399-401. [all data]

Ueberreiter and Orthmann, 1950
Ueberreiter, K.; Orthmann, H.-J., Specifische Wärme, spezifisches Volumen, Temperatur- und Wärme-leittähigkeit einiger disubstituierter Benzole und polycyclischer Systeme, Z. Natursforsch. 5a, 1950, 101-108. [all data]

Andrews, Lynn, et al., 1926
Andrews, D.H.; Lynn, G.; Johnston, J., The heat capacities and heat of crystallization of some isomeric aromatic compounds, J. Am. Chem. Soc., 1926, 48, 1274-1287. [all data]

Lange, 1924
Lange, F., Untersuchungen über die spezifische Wärme bei tiefen Temperaturen, Z. Phys. Chem., 1924, 110, 343-362. [all data]

Andrews, Lynn, et al., 1926, 2
Andrews, D.H.; Lynn, G.; Johnston, J., The Heat Capacities and Heat of Crystallization of Some Isomeric Aromatic Compounds, J. Am. Chem. Soc., 1926, 48, 1274. [all data]

Rojas-Aguilar, Flores-Lara, et al., 2004
Rojas-Aguilar, Aarón; Flores-Lara, Honorio; Martinez-Herrera, Melchor; Ginez-Carbajal, Francisco, Thermochemistry of benzoquinones, The Journal of Chemical Thermodynamics, 2004, 36, 6, 453-463, https://doi.org/10.1016/j.jct.2004.03.002 . [all data]

Coolidge and Coolidge, 1927
Coolidge, A.S.; Coolidge, M.S., The sublimation pressures of substituted quinones and hydroquinones, J. Am. Chem. Soc., 1927, 49, 100-104. [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]

de Kruif, 1981
de Kruif, C.G., Thermodynamic properties of 1,4-benzoquinone (BQ), 1,4-hydroquinone (HQ), 1,4-naphthoquinone (NQ), 1,4-naphthohydroquinone (NHQ), and the complexes BQ--HQ 1:1, NQ--HQ 1:1, NQ--NHQ 2:1, and NQ--NHQ 1:1, J. Chem. Phys., 1981, 74, 10, 5838, https://doi.org/10.1063/1.440898 . [all data]

Acree, 1991
Acree, William E., Thermodynamic properties of organic compounds: enthalpy of fusion and melting point temperature compilation, Thermochimica Acta, 1991, 189, 1, 37-56, https://doi.org/10.1016/0040-6031(91)87098-H . [all data]

Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G., Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update, J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018 . [all data]

Fu, Yang, et al., 2011
Fu, Q.A.; Yang, J.L.; Wang, X.B., On the Electronic Structures and Electron Affinities of the m-Benzoquinone (BQ) Diradical and the o-, p-BQ Molecules: A Synergetic Photoelectron Spectroscopic and Theoretical Study, J. Phys. Chem. A, 2011, 115, 15, 3201-3207, https://doi.org/10.1021/jp1120542 . [all data]

Schiedt and Weinkauf, 1999
Schiedt, J.; Weinkauf, R., Resonant Photodetachment via Shape and Feshbach Resonances: p-Benzoquinone Anions as a Model System, J. Chem. Phys., 1999, 110, 1, 304, https://doi.org/10.1063/1.478066 . [all data]

Siegert, Vogeler, et al., 2011
Siegert, S.; Vogeler, F.; Marian, C.M.; Weinkauf, R., Throwing light on dark states of alpha-oligothiophenes of chain lengths 2 to 6: radical anion photoelectron spectroscopy and excited-state theory, Phys. Chem. Chem. Phys., 2011, 13, 21, 10350-10363, https://doi.org/10.1039/c0cp02712j . [all data]

Heinis, Chowdhury, et al., 1988
Heinis, T.; Chowdhury, S.; Scott, S.L.; Kebarle, P., Electron Affinities of Benzo-, Naphtho-, and Anthraquinones Determined from Gas-Phase Equilibria Measurements, J. Am. Chem. Soc., 1988, 110, 2, 400, https://doi.org/10.1021/ja00210a015 . [all data]

Fukuda and McIver, 1985
Fukuda, E.K.; McIver, R.T., Jr., Relative electron affinities of substituted benzophenones, nitrobenzenes, and quinones. [Anchored to EA(SO2) from 74CEL/BEN], J. Am. Chem. Soc., 1985, 107, 2291. [all data]

Marks, Comita, et al., 1985
Marks, J.; Comita, P.B.; Brauman, J.I., Threshold resonances in electron photodetachment spectra. Structural evidence for dipole-supported states, J. Am. Chem. Soc., 1985, 107, 3718. [all data]

Cooper, Naff, et al., 1975
Cooper, C.D.; Naff, W.T.; Compton, R.N., Negative ion properties of p-benzoquinone: Electron affinity and compound states, J. Chem. Phys., 1975, 63, 2752. [all data]

Farragher and Page, 1966
Farragher, A.L.; Page, F.M., Experimental Determination of Electron Affinities. Part 9. - Benzoquinone, Chloranil and Related Compounds, Trans. Farad. Soc., 1966, 62, 3072, https://doi.org/10.1039/tf9666203072 . [all data]

Lauer, Schafer, et al., 1975
Lauer, G.; Schafer, W.; Schweig, A., Assignment of the four lowest ionized states of p-benzoquinone and the question of "lone pair" splitting in this system, Chem. Phys. Lett., 1975, 33, 312. [all data]

Kobayashi, 1975
Kobayashi, T., Photoelectron spectra of p-benzoquinones, J. Electron. Spectrosc. Relat. Phenom., 1975, 7, 349. [all data]

Kotov and Potapov, 1972
Kotov, B.V.; Potapov, V.K., Ionization potentials of strong organic electron acceptors, Khim. Vys. Energ., 1972, 6, 375. [all data]

Potapov and Sorokin, 1971
Potapov, V.K.; Sorokin, V.V., Photoionization and ion-molecule reactions in quinones and alcohols, High Energy Chem., 1971, 5, 435, In original 487. [all data]

Dewar and Worley, 1969
Dewar, M.J.S.; Worley, S.D., Photoelectron spectra of molecules. I. Ionization potentials of some organic molecules and their interpretation, J. Chem. Phys., 1969, 50, 654. [all data]

Terenin, 1961
Terenin, A., Charge transfer in organic solids, induced by light, Proc. Chem. Soc., London, 1961, 321. [all data]

Vilesov and Terenin, 1957
Vilesov, F.I.; Terenin, A.N., The photoionization of the vapors of certain organic compounds, Dokl. Akad. Nauk SSSR, 1957, 115, 744, In original 539. [all data]

Bock, Mohmand, et al., 1983
Bock, H.; Mohmand, S.; Hirabayashi, T.; Maier, G.; Reisenauer, H.P., Photoelektronen-spektroskopischer nachweis und matrix-isolierung von thio-para-benzochinonen, Chem. Ber., 1983, 116, 273. [all data]

Dougherty and McGlynn, 1977
Dougherty, D.; McGlynn, S.P., Photoelectron spectroscopy of carbonyls. 1,4-Benzoquinones, J. Am. Chem. Soc., 1977, 99, 3234. [all data]

Cowan, Gleiter, et al., 1971
Cowan, D.O.; Gleiter, R.; Hashmall, J.A.; Heilbronner, E.; Hornung, V., Interaction between the orbitals of lone pair electrons in dicarbonyl compounds, Angew. Chem. Int. Ed. Engl., 1971, 10, 401. [all data]

Llobera and García-Raso, 1987
Llobera, A.; García-Raso, A., Gas chromatographic behaviour of several p-quinones, J. Chromatogr., 1987, 393, 2, 305-311, https://doi.org/10.1016/S0021-9673(01)94227-X . [all data]

Zenkevich, 2005
Zenkevich, I.G., Experimentally measured retention indices., 2005. [all data]

Chen, Keeran, et al., 2002
Chen, P.H.; Keeran, W.S.; Van Ausdale, W.A.; Schindler, D.R.; Roberts, D.W., Application of Lee retention indices to the confirmation of tentatively identified compounds from GC/MS analysis of environmental samples, Technical paper, Analytical Services Division, Environmental ScienceEngineering, Inc, PO Box 1703, Gainesville, FL 32602, 2002, 11. [all data]


Notes

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), UV/Visible spectrum, Gas Chromatography, NIST Free Links, References