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
Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, 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:
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
Go To: Top, Phase change data, Gas phase ion energetics data, IR Spectrum, 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
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
Go To: Top, Phase change data, Reaction thermochemistry data, IR Spectrum, References, Notes
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
Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, References, Notes
Data compiled by: Coblentz Society, Inc.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
References
Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR 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]
Notes
Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, 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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