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Anthracene, 9-methyl-

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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

Quantity Value Units Method Reference Comment
Tfus354.KN/ABradsher and Webster, 1957Uncertainty assigned by TRC = 2. K; TRC
Tfus354.KN/AHuang-Minlon, 1949Uncertainty assigned by TRC = 4. K; TRC
Quantity Value Units Method Reference Comment
Deltavap88.1 ± 1.0kJ/molCGCHanshaw, Nutt, et al., 2008AC
Quantity Value Units Method Reference Comment
Deltasub101.8 ± 1.0kJ/molMERibeiro da Silva, Amaral, et al., 2006Based on data from 329. - 345. K.; AC

Reduced pressure boiling point

Tboil (K) Pressure (bar) Reference Comment
469.70.016Weast and Grasselli, 1989BS

Enthalpy of vaporization

DeltavapH (kJ/mol) Temperature (K) Method Reference Comment
98.9369.AStephenson and Malanowski, 1987Based on data from 354. - 402. K.; AC
58.5465.N/ASivaraman and Kobayashi, 1983Based on data from 423. - 587. K.; AC
58.1515.N/ASivaraman and Kobayashi, 1983Based on data from 423. - 515. K.; AC
56.5555.N/ASivaraman and Kobayashi, 1983Based on data from 423. - 515. K.; AC

Enthalpy of sublimation

DeltasubH (kJ/mol) Temperature (K) Method Reference Comment
99.8 ± 1.0337.MERibeiro da Silva, Amaral, et al., 2006Based on data from 329. - 345. K.; AC

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

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

By formula: C15H11- + H+ = C15H12

Quantity Value Units Method Reference Comment
Deltar1515. ± 10.kJ/molG+TSBartmess and Griffiths, 1990gas phase; Isomer 9-methylene-9,10-dihydroanthracene: «DELTA»G=349.0±3.0, «DELTA»S=27.0, «DELTA»H=357.1;DH: Zhang, Bordwell, et al., 1993; B
Quantity Value Units Method Reference Comment
Deltar1486. ± 9.6kJ/molIMREBartmess and Griffiths, 1990gas phase; Isomer 9-methylene-9,10-dihydroanthracene: «DELTA»G=349.0±3.0, «DELTA»S=27.0, «DELTA»H=357.1;DH: Zhang, Bordwell, et al., 1993; B

C21H12N4 = Tetracyanoethylene + Anthracene, 9-methyl-

By formula: C21H12N4 = C6N4 + C15H12

Quantity Value Units Method Reference Comment
Deltar62.3kJ/molKinLotfi and Roberts, 1979liquid phase; solvent: CCl4; Spectrophotometrically; ALS

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)896.5kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity865.8kJ/molN/AHunter and Lias, 1998HL

Proton affinity at 298K

Proton affinity (kJ/mol) Reference Comment
893.7Aue, Guidoni, et al., 2000Experimental literature data re-evaluated by the authors using ab initio protonation entropies; MM

Gas basicity at 298K

Gas basicity (review) (kJ/mol) Reference Comment
865.7Aue, 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
Deltar1515. ± 10.kJ/molG+TSBartmess and Griffiths, 1990gas phase; Isomer 9-methylene-9,10-dihydroanthracene: «DELTA»G=349.0±3.0, «DELTA»S=27.0, «DELTA»H=357.1;DH: Zhang, Bordwell, et al., 1993; B
Quantity Value Units Method Reference Comment
Deltar1486. ± 9.6kJ/molIMREBartmess and Griffiths, 1990gas phase; Isomer 9-methylene-9,10-dihydroanthracene: «DELTA»G=349.0±3.0, «DELTA»S=27.0, «DELTA»H=357.1;DH: Zhang, Bordwell, et al., 1993; B

IR Spectrum

Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible spectrum, References, Notes

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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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 Chemical Concepts
NIST MS number 152558

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

Go To: Top, 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: 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)

References

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

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

Bradsher and Webster, 1957
Bradsher, C.K.; Webster, S.T., A New Base-catalyzed Cyclization Reaction, J. Am. Chem. Soc., 1957, 79, 393-5. [all data]

Huang-Minlon, 1949
Huang-Minlon, Reduction of Steroid Ketones and Other Carbonyl Compounds by Modified Wolff-Kishner Method, J. Am. Chem. Soc., 1949, 71, 3301. [all data]

Hanshaw, Nutt, et al., 2008
Hanshaw, William; Nutt, Marjorie; Chickos, James S., Hypothetical Thermodynamic Properties. Subcooled Vaporization Enthalpies and Vapor Pressures of Polyaromatic Hydrocarbons, J. Chem. Eng. Data, 2008, 53, 8, 1903-1913, https://doi.org/10.1021/je800300x . [all data]

Ribeiro da Silva, Amaral, et al., 2006
Ribeiro da Silva, Manuel A.V.; Amaral, Luísa M.P.F.; Santos, Ana Filipa L.O.M.; Gomes, José R.B., Thermochemistry of some alkylsubstituted anthracenes, The Journal of Chemical Thermodynamics, 2006, 38, 4, 367-375, https://doi.org/10.1016/j.jct.2005.06.001 . [all data]

Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [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]

Sivaraman and Kobayashi, 1983
Sivaraman, Alwarappa; Kobayashi, Riki, Vapor pressures and enthalpies of vaporization of thianthrene, acridine, and 9-methylanthracene at elevated temperatures, The Journal of Chemical Thermodynamics, 1983, 15, 12, 1127-1135, https://doi.org/10.1016/0021-9614(83)90003-4 . [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]

Lotfi and Roberts, 1979
Lotfi, M.; Roberts, R.M.G., Kinetics and mechanism of Diels-Alder additions of tetracyanoethylene to anthracene derivatives - I. Substituent effects, Tetrahedron, 1979, 35, 2131-2136. [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]

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]

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]


Notes

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