Anthracene, 9-methyl-

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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

Data compiled as indicated in comments:
B - John E. Bartmess
MM - Michael M. Meot-Ner (Mautner)
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

Quantity Value Units Method Reference Comment
Proton affinity (review)214.3kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity206.9kcal/molN/AHunter and Lias, 1998HL

Proton affinity at 298K

Proton affinity (kcal/mol) Reference Comment
213.6Aue, Guidoni, et al., 2000Experimental literature data re-evaluated by the authors using ab initio protonation entropies; MM

Gas basicity at 298K

Gas basicity (review) (kcal/mol) Reference Comment
206.9Aue, Guidoni, et al., 2000Experimental literature data re-evaluated by the authors using ab initio protonation entropies; MM

Ionization energy determinations

IE (eV) Method Reference Comment
7.31 ± 0.05EQMautner(Meot-Ner), 1980LLK
7.24 ± 0.03PEKlasinc, Kovac, et al., 1978LLK
7.25PEHino and Inokuchi, 1974LLK
7.46 ± 0.03EINounou, 1966RDSH
7.24 ± 0.03PEKlasinc, Kovac, et al., 1978Vertical value; LLK
7.27PEJongsma, Vermeer, et al., 1975Vertical value; LLK

De-protonation reactions

C15H11- + Hydrogen cation = Anthracene, 9-methyl-

By formula: C15H11- + H+ = C15H12

Quantity Value Units Method Reference Comment
Δr362.2 ± 2.4kcal/molG+TSBartmess and Griffiths, 1990gas phase; Isomer 9-methylene-9,10-dihydroanthracene: ΔG=349.0±3.0, ΔS=27.0, ΔH=357.1;DH: Zhang, Bordwell, et al., 1993; B
Quantity Value Units Method Reference Comment
Δr355.1 ± 2.3kcal/molIMREBartmess and Griffiths, 1990gas phase; Isomer 9-methylene-9,10-dihydroanthracene: ΔG=349.0±3.0, ΔS=27.0, ΔH=357.1;DH: Zhang, Bordwell, et al., 1993; B

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

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


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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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 Chemical Concepts
NIST MS number 152558

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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 Clar, 1949
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. 697
Instrument n.i.g.
Melting point 81.5
Boiling point 196-7(12)

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
PackedOV-101230.1999.Grimmer and Böhnke, 1975Gas Chrom Q; Column length: 10. m
CapillaryOV-101230.1999.Grimmer and Böhnke, 1972N2; Column length: 50. m; Column diameter: 0.50 mm

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

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Column type Active phase I Reference Comment
CapillaryOV-11941.2Zhang, Shen, et al., 200025. m/0.2 mm/0.33 μm, 5. K/min; Tstart: 100. C; Tend: 180. C
CapillaryDB-51980.Rostad and Pereira, 198630. m/0.26 mm/0.25 μm, He, 50. C @ 4. min, 6. K/min, 300. C @ 20. min

Normal alkane RI, non-polar column, temperature ramp

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Column type Active phase I Reference Comment
CapillaryUltra-11926.Elizalde-González, Hutfliess, et al., 199650. m/0.2 mm/0.33 μm, H2, 3. K/min, 300. C @ 35. min; Tstart: 60. C

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

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Column type Active phase I Reference Comment
PackedOV-1011999.Kaliszan and Lamparczyk, 1978Program: not specified

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

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Column type Active phase I Reference Comment
CapillaryHP-5312.3Wang, Hou, et al., 200730. m/0.30 mm/0.25 μm, Helium, 50. C @ 5. min, 5. K/min, 200. C @ 15. min
CapillaryHP-5309.19Piao, Chu, et al., 199930. m/0.25 mm/0.25 μm, 50. C @ 2. min, 4. K/min, 280. C @ 20. min
CapillarySE-54329.09Ivanov and Golovko, 1994He, 3. K/min, 260. C @ 40. min; Column length: 25. m; Tstart: 130. C
CapillarySE-54329.36Guillén, Blanco, et al., 198920. m/0.22 mm/0.20 μm, He, 4. K/min; Tstart: 50. C; Tend: 300. C
CapillaryDB-5329.52Rostad and Pereira, 198630. m/0.26 mm/0.25 μm, He, 50. C @ 4. min, 6. K/min, 300. C @ 20. min
CapillarySE-52329.13Lee, Vassilaros, et al., 197912. m/0.3 mm/0.34 μm, He, 2. K/min; Tstart: 50. C; Tend: 250. C

Lee's RI, non-polar column, custom temperature program

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Column type Active phase I Reference Comment
CapillaryDB-5MS309.7Aracil, Font, et al., 2005Column length: 60. m; Column diameter: 0.25 mm; Program: not specified
CapillaryOV-101330.1Tucminen, Wickstrom, et al., 1986Program: not specified
CapillarySE-52324.16Shlyakhov, 1984Program: not specified
CapillarySE-52327.74Shlyakhov, 1984Program: not specified
CapillarySE-52329.13Shlyakhov, 1984Program: not specified

References

Go To: Top, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, Notes

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

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]

Aue, Guidoni, et al., 2000
Aue, D.H.; Guidoni, M.; Betowski, L.D., Ab initio calculated gas-phase basicities of polynuclear aromatic hydrocarbons, Int. J. Mass Spectrom., 2000, 201, 283. [all data]

Mautner(Meot-Ner), 1980
Mautner(Meot-Ner), M., Ion thermochemistry of low volatility compounds in the gas phase. 3. Polycyclic aromatics: Ionization energies, proton, and hydrogen affinities. Extrapolations to graphite, J. Phys. Chem., 1980, 84, 2716. [all data]

Klasinc, Kovac, et al., 1978
Klasinc, L.; Kovac, B.; Schoof, S.; Gusten, H., Photoelectron spectroscopy of 9-substituted anthracenes, Croat. Chem. Acta., 1978, 51, 307. [all data]

Hino and Inokuchi, 1974
Hino, S.; Inokuchi, H., Photoelectron spectrum (He I) of 9-methylanthracene, Chem. Lett., 1974, 363. [all data]

Nounou, 1966
Nounou, P., Etude des composes aromatiques par spectrometrie de masse. I. Mesure des potentials d'ionisation et d'apparition par la methode du potential retardateur et interpretation des courbes d'ionisation differentielle, J. Chim. Phys., 1966, 63, 994. [all data]

Jongsma, Vermeer, et al., 1975
Jongsma, C.; Vermeer, H.; Bickelhaupt, F.; Schafer, W.; Schweig, A., 10-methyl-9-phosphaanthracene, Tetrahedron, 1975, 31, 2931. [all data]

Bartmess and Griffiths, 1990
Bartmess, J.E.; Griffiths, S.S., Tautomerization Energetics of Benzoannelated Toluenes, J. Am. Chem. Soc., 1990, 112, 8, 2932, https://doi.org/10.1021/ja00164a014 . [all data]

Zhang, Bordwell, et al., 1993
Zhang, X.M.; Bordwell, F.G.; Bares, J.E.; Cheng, J.P.; Petrie, B.C., Homolytic Bond Dissociation Energies of the Acidic C-H Bonds in alpha-Substituted and 10-Substituted 9-Methylanthracenes and Their Related Radical Anions, J. Org. Chem., 1993, 58, 11, 3051, https://doi.org/10.1021/jo00063a025 . [all data]

Clar, 1949
Clar, E., Das anellierungsprinzip und die resonanz in aromatischen kohlenwasserstoffen (aromatische kohlenwasserstoffe, LIV. Mitteil), Chem. Ber., 1949, 82, 6, 495-514. [all data]

Grimmer and Böhnke, 1975
Grimmer, G.; Böhnke, H., Polycyclic aromatic hydrocarbon profile analysis of high-protein foods, oils, and fats by gas chromatography, J. Ass. Offic. Anal. Chem, 1975, 58, 4, 725-733. [all data]

Grimmer and Böhnke, 1972
Grimmer, G.; Böhnke, H., Bestimmung des Gesamtgehaltes aller polycyclischen aromatischen Kohlenwasserstoffe in Luftstaub und Kraftfahrzeugabgas mit der Capillar-Gas-Chromatographie, Z. Anal. Chem., 1972, 261, 4-5, 310-314, https://doi.org/10.1007/BF00786987 . [all data]

Zhang, Shen, et al., 2000
Zhang, M.-J.; Shen, S.-D.; Chen, S.-Y.; Sun, Y.-H., Analysis of heavy oil fractions in high-temperature coal tar by capillary gas chromatography/fourier transform infrared spectrometry, Chin. J. Chromatogr., 2000, 18, 3, 241-246. [all data]

Rostad and Pereira, 1986
Rostad, C.E.; Pereira, W.E., Kovats and Lee retention indices determined by gas chromatography/mass spectrometry for organic compounds of environmental interest, J. Hi. Res. Chromatogr. Chromatogr. Comm., 1986, 9, 6, 328-334, https://doi.org/10.1002/jhrc.1240090603 . [all data]

Elizalde-González, Hutfliess, et al., 1996
Elizalde-González, M.P.; Hutfliess, M.; Hedden, K., Retention index system, adsorption characteristics, and sructure correlations of polycyclic aromatic hydrocarbons in fuels, J. Hi. Res. Chromatogr., 1996, 19, 6, 345-352, https://doi.org/10.1002/jhrc.1240190608 . [all data]

Kaliszan and Lamparczyk, 1978
Kaliszan, R.; Lamparczyk, H., A Relationship between the Connectivity Indices and Retention Indices of Polycyclic Aromatic Hydrocarbons, J. Chromatogr. Sci., 1978, 16, 6, 246-248, https://doi.org/10.1093/chromsci/16.6.246 . [all data]

Wang, Hou, et al., 2007
Wang, G.; Hou, Z.; Sun, Y.; Liu, Y.; Xie, B.; Liu, S., Investigation of pyrolysis behavior of fenoxycarb using PY-GC-MS assisted with chemometric methods, Chem. Anal., 2007, 52, 141-156. [all data]

Piao, Chu, et al., 1999
Piao, M.; Chu, S.; Zheng, M.; Xu, X., Characterization of the combustion products of polyethylene, Chemosphere, 1999, 39, 9, 1497-1512, https://doi.org/10.1016/S0045-6535(99)00054-5 . [all data]

Ivanov and Golovko, 1994
Ivanov, V.I.; Golovko, A.K., Investigation of the composition of petroleum anthracene hydrocarbons, Pet. Chem. USSR (Engl. Transl.), 1994, 34, 6, 504-512. [all data]

Guillén, Blanco, et al., 1989
Guillén, M.D.; Blanco, J.; Bermejo, J.; Blanco, C.G., Temperature programmed retention indices of some PAHs on Capillary columns coated with OV-1701 and SE-54, J. Hi. Res. Chromatogr., 1989, 12, 8, 552-554, https://doi.org/10.1002/jhrc.1240120816 . [all data]

Lee, Vassilaros, et al., 1979
Lee, M.L.; Vassilaros, D.L.; White, C.M.; Novotny, M., Retention Indices for Programmed-Temperature Capillary-Column Gas Chromatography of Polycyclic Aromatic Hydrocarbons, Anal. Chem., 1979, 51, 6, 768-773, https://doi.org/10.1021/ac50042a043 . [all data]

Aracil, Font, et al., 2005
Aracil, I.; Font, R.; Conesa, J.A., Semivolatile and volatile compounds from the pyrolysis and combustion of polyvinyl chloride, J. Anal. Appl. Pyrolysis, 2005, 74, 1-2, 465-478, https://doi.org/10.1016/j.jaap.2004.09.008 . [all data]

Tucminen, Wickstrom, et al., 1986
Tucminen, A.; Wickstrom, K.; Pyysalo, H., Determination of Polycyclic Aromatic Compounds by GLC-Selected Ion Monitoring (SIM) Technique, J. Hi. Res. Chromatogr. Chromatogr. Comm., 1986, 9, 8, 469-471, https://doi.org/10.1002/jhrc.1240090813 . [all data]

Shlyakhov, 1984
Shlyakhov, A.F., Gas chromatography in organic geochemistry, Nedra, Moscow, 1984, 221. [all data]


Notes

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