Anthracene, 9-methyl-
- Formula: C15H12
- Molecular weight: 192.2558
- IUPAC Standard InChIKey: CPGPAVAKSZHMBP-UHFFFAOYSA-N
- CAS Registry Number: 779-02-2
- Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript. - Other names: 9-Methylanthracene
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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 |
---|---|---|---|---|---|
Tfus | 354. | K | N/A | Bradsher and Webster, 1957 | Uncertainty assigned by TRC = 2. K; TRC |
Tfus | 354. | K | N/A | Huang-Minlon, 1949 | Uncertainty assigned by TRC = 4. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 88.1 ± 1.0 | kJ/mol | CGC | Hanshaw, Nutt, et al., 2008 | AC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 101.8 ± 1.0 | kJ/mol | ME | Ribeiro da Silva, Amaral, et al., 2006 | Based on data from 329. to 345. K.; AC |
Reduced pressure boiling point
Tboil (K) | Pressure (bar) | Reference | Comment |
---|---|---|---|
469.7 | 0.016 | Weast and Grasselli, 1989 | BS |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
98.9 | 369. | A | Stephenson and Malanowski, 1987 | Based on data from 354. to 402. K.; AC |
58.5 | 465. | N/A | Sivaraman and Kobayashi, 1983 | Based on data from 423. to 587. K.; AC |
58.1 | 515. | N/A | Sivaraman and Kobayashi, 1983 | Based on data from 423. to 515. K.; AC |
56.5 | 555. | N/A | Sivaraman and Kobayashi, 1983 | Based on data from 423. to 515. K.; AC |
Enthalpy of sublimation
ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
99.8 ± 1.0 | 337. | ME | Ribeiro da Silva, Amaral, et al., 2006 | Based on data from 329. to 345. K.; AC |
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- + =
By formula: C15H11- + H+ = C15H12
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1515. ± 10. | kJ/mol | G+TS | Bartmess and Griffiths, 1990 | gas 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 |
ΔrG° | 1486. ± 9.6 | kJ/mol | IMRE | Bartmess and Griffiths, 1990 | gas 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 |
C21H12N4 = +
By formula: C21H12N4 = C6N4 + C15H12
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 62.3 | kJ/mol | Kin | Lotfi and Roberts, 1979 | liquid 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) | 896.5 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 865.8 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Proton affinity at 298K
Proton affinity (kJ/mol) | Reference | Comment |
---|---|---|
893.7 | Aue, Guidoni, et al., 2000 | Experimental literature data re-evaluated by the authors using ab initio protonation entropies; MM |
Gas basicity at 298K
Gas basicity (review) (kJ/mol) | Reference | Comment |
---|---|---|
865.7 | Aue, Guidoni, et al., 2000 | Experimental literature data re-evaluated by the authors using ab initio protonation entropies; MM |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
7.31 ± 0.05 | EQ | Mautner(Meot-Ner), 1980 | LLK |
7.24 ± 0.03 | PE | Klasinc, Kovac, et al., 1978 | LLK |
7.25 | PE | Hino and Inokuchi, 1974 | LLK |
7.46 ± 0.03 | EI | Nounou, 1966 | RDSH |
7.24 ± 0.03 | PE | Klasinc, Kovac, et al., 1978 | Vertical value; LLK |
7.27 | PE | Jongsma, Vermeer, et al., 1975 | Vertical value; LLK |
De-protonation reactions
C15H11- + =
By formula: C15H11- + H+ = C15H12
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1515. ± 10. | kJ/mol | G+TS | Bartmess and Griffiths, 1990 | gas 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 |
ΔrG° | 1486. ± 9.6 | kJ/mol | IMRE | Bartmess and Griffiths, 1990 | gas 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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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 |
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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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
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Packed | OV-101 | 230. | 1999. | Grimmer and Böhnke, 1975 | Gas Chrom Q; Column length: 10. m |
Capillary | OV-101 | 230. | 1999. | Grimmer and Böhnke, 1972 | N2; Column length: 50. m; Column diameter: 0.50 mm |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | OV-1 | 1941.2 | Zhang, Shen, et al., 2000 | 25. m/0.2 mm/0.33 μm, 5. K/min; Tstart: 100. C; Tend: 180. C |
Capillary | DB-5 | 1980. | Rostad and Pereira, 1986 | 30. 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
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Ultra-1 | 1926. | Elizalde-González, Hutfliess, et al., 1996 | 50. 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
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Packed | OV-101 | 1999. | Kaliszan and Lamparczyk, 1978 | Program: not specified |
Lee's RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | HP-5 | 312.3 | Wang, Hou, et al., 2007 | 30. m/0.30 mm/0.25 μm, Helium, 50. C @ 5. min, 5. K/min, 200. C @ 15. min |
Capillary | HP-5 | 309.19 | Piao, Chu, et al., 1999 | 30. m/0.25 mm/0.25 μm, 50. C @ 2. min, 4. K/min, 280. C @ 20. min |
Capillary | SE-54 | 329.09 | Ivanov and Golovko, 1994 | He, 3. K/min, 260. C @ 40. min; Column length: 25. m; Tstart: 130. C |
Capillary | SE-54 | 329.36 | Guillén, Blanco, et al., 1989 | 20. m/0.22 mm/0.20 μm, He, 4. K/min; Tstart: 50. C; Tend: 300. C |
Capillary | DB-5 | 329.52 | Rostad and Pereira, 1986 | 30. m/0.26 mm/0.25 μm, He, 50. C @ 4. min, 6. K/min, 300. C @ 20. min |
Capillary | SE-52 | 329.13 | Lee, Vassilaros, et al., 1979 | 12. 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
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-5MS | 309.7 | Aracil, Font, et al., 2005 | Column length: 60. m; Column diameter: 0.25 mm; Program: not specified |
Capillary | OV-101 | 330.1 | Tucminen, Wickstrom, et al., 1986 | Program: not specified |
Capillary | SE-52 | 324.16 | Shlyakhov, 1984 | Program: not specified |
Capillary | SE-52 | 327.74 | Shlyakhov, 1984 | Program: not specified |
Capillary | SE-52 | 329.13 | Shlyakhov, 1984 | Program: not specified |
References
Go To: Top, Phase change data, Reaction thermochemistry data, 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.
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
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Reduction of Steroid Ketones and Other Carbonyl Compounds by Modified Wolff-Kishner Method,
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Hanshaw, Nutt, et al., 2008
Hanshaw, William; Nutt, Marjorie; Chickos, James S.,
Hypothetical Thermodynamic Properties. Subcooled Vaporization Enthalpies and Vapor Pressures of Polyaromatic Hydrocarbons,
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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,
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Weast and Grasselli, 1989
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Stephenson and Malanowski, 1987
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Sivaraman and Kobayashi, 1983
Sivaraman, Alwarappa; Kobayashi, Riki,
Vapor pressures and enthalpies of vaporization of thianthrene, acridine, and 9-methylanthracene at elevated temperatures,
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Bartmess and Griffiths, 1990
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Tautomerization Energetics of Benzoannelated Toluenes,
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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,
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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,
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Aue, Guidoni, et al., 2000
Aue, D.H.; Guidoni, M.; Betowski, L.D.,
Ab initio calculated gas-phase basicities of polynuclear aromatic hydrocarbons,
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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,
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Klasinc, Kovac, et al., 1978
Klasinc, L.; Kovac, B.; Schoof, S.; Gusten, H.,
Photoelectron spectroscopy of 9-substituted anthracenes,
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Hino and Inokuchi, 1974
Hino, S.; Inokuchi, H.,
Photoelectron spectrum (He I) of 9-methylanthracene,
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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,
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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),
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Grimmer and Böhnke, 1975
Grimmer, G.; Böhnke, H.,
Polycyclic aromatic hydrocarbon profile analysis of high-protein foods, oils, and fats by gas chromatography,
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Grimmer and Böhnke, 1972
Grimmer, G.; Böhnke, H.,
Bestimmung des Gesamtgehaltes aller polycyclischen aromatischen Kohlenwasserstoffe in Luftstaub und Kraftfahrzeugabgas mit der Capillar-Gas-Chromatographie,
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. [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,
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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,
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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,
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Kaliszan and Lamparczyk, 1978
Kaliszan, R.; Lamparczyk, H.,
A Relationship between the Connectivity Indices and Retention Indices of Polycyclic Aromatic Hydrocarbons,
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Wang, Hou, et al., 2007
Wang, G.; Hou, Z.; Sun, Y.; Liu, Y.; Xie, B.; Liu, S.,
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Characterization of the combustion products of polyethylene,
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Ivanov, V.I.; Golovko, A.K.,
Investigation of the composition of petroleum anthracene hydrocarbons,
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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,
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Retention Indices for Programmed-Temperature Capillary-Column Gas Chromatography of Polycyclic Aromatic Hydrocarbons,
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Semivolatile and volatile compounds from the pyrolysis and combustion of polyvinyl chloride,
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Gas chromatography in organic geochemistry, Nedra, Moscow, 1984, 221. [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, Gas Chromatography, References
- Symbols used in this document:
Tboil Boiling point Tfus Fusion (melting) point ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔsubH Enthalpy of sublimation ΔsubH° Enthalpy of sublimation at standard conditions ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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