Benzo[ghi]perylene
- Formula: C22H12
- Molecular weight: 276.3307
- IUPAC Standard InChIKey: GYFAGKUZYNFMBN-UHFFFAOYSA-N
- CAS Registry Number: 191-24-2
- 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: Benzo-1,12-perylene; 1,12-Benzoperylene; 1,12-Benzperylene
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Gas phase thermochemistry data
Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, 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: Glushko Thermocenter, Russian Academy of Sciences, Moscow
Constant pressure heat capacity of gas
Cp,gas (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
47.36 | 50. | Dorofeeva O.V., 1988 | Recommended values were calculated statistically mechanically using force field approximation for polycyclic aromatic hydrocarbons to estimate the needed vibrational frequencies (see also [ Dorofeeva O.V., 1986, Moiseeva N.F., 1989]). These functions are reproduced in the reference book [ Frenkel M., 1994]. |
80.71 | 100. | ||
123.88 | 150. | ||
172.19 | 200. | ||
246.03 | 273.15 | ||
271.0 ± 4.0 | 298.15 | ||
272.83 | 300. | ||
365.55 | 400. | ||
442.58 | 500. | ||
504.03 | 600. | ||
552.90 | 700. | ||
592.19 | 800. | ||
624.23 | 900. | ||
650.67 | 1000. | ||
672.72 | 1100. | ||
691.24 | 1200. | ||
706.92 | 1300. | ||
720.28 | 1400. | ||
731.73 | 1500. |
Phase change data
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, 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:
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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tfus | 553.0 | K | N/A | Smith, 1980 | Uncertainty assigned by TRC = 0.2 K; TRC |
Tfus | 554.2 | K | N/A | Casellato, Vecchi, et al., 1973 | Uncertainty assigned by TRC = 0.4 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 128.9 ± 1.5 | kJ/mol | CGC | Hanshaw, Nutt, et al., 2008 | AC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 126. | kJ/mol | V | Wakayama and Inokuchi, 1967 | ALS |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
96.1 | 398. | GC | Lei, Chankalal, et al., 2002 | Based on data from 323. to 473. K.; AC |
Enthalpy of sublimation
ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
129.9 | 383. | GS | Nass, Lenoir, et al., 1995 | Based on data from 313. to 453. K.; AC |
127.8 | 404. | ME | Stephenson and Malanowski, 1987 | Based on data from 389. to 468. K. See also Murray, Pottie, et al., 1974.; AC |
135.1 | 465. | A | Stephenson and Malanowski, 1987 | Based on data from 450. to 510. K.; AC |
125.5 | 478. | ME | Wakayama and Inokuchi, 1967, 2 | Based on data from 454. to 502. K.; AC |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
17.37 | 554.2 | Acree, 1991 | AC |
Reaction thermochemistry data
Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, 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: Michael M. Meot-Ner (Mautner) and Sharon G. Lias
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
By formula: C22H13+ + C22H12 = (C22H13+ • C22H12)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 89.5 | kJ/mol | PHPMS | Meot-Ner (Mautner), 1980 | gas phase; Entropy change calculated or estimated |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 120. | J/mol*K | N/A | Meot-Ner (Mautner), 1980 | gas phase; Entropy change calculated or estimated |
Free energy of reaction
ΔrG° (kJ/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
44.4 | 385. | PHPMS | Meot-Ner (Mautner), 1980 | gas phase; Entropy change calculated or estimated |
By formula: C22H12+ + C22H12 = (C22H12+ • C22H12)
Bond type: Charge transfer bond (positive ion)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 90.4 | kJ/mol | PHPMS | Meot-Ner (Mautner), 1980 | gas phase |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 110. | J/mol*K | PHPMS | Meot-Ner (Mautner), 1980 | gas phase |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, 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
L - Sharon G. Lias
Data compiled as indicated in comments:
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
B - John E. Bartmess
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 7.17 ± 0.02 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 876.0 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 845.2 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Electron affinity determinations
EA (eV) | Method | Reference | Comment |
---|---|---|---|
0.42 ± 0.10 | CIDC | Chen and Cooks, 1995 | B |
Proton affinity at 298K
Proton affinity (kJ/mol) | Reference | Comment |
---|---|---|
877.8 | 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 |
---|---|---|
850.6 | 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 |
---|---|---|---|
7.20 ± 0.05 | EQ | Mautner(Meot-Ner), 1980 | LLK |
7.15 | PE | Clar and Schmidt, 1977 | LLK |
7.19 ± 0.01 | PE | Boschi, Murrell, et al., 1972 | LLK |
7.35 | CTS | Briegleb, 1964 | RDSH |
7.13 | CTS | Matsen, 1956 | RDSH |
7.15 | PE | Clar and Schmidt, 1977 | Vertical value; LLK |
7.15 | PE | Clar and Schmidt, 1976 | Vertical value; LLK |
References
Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Dorofeeva O.V., 1988
Dorofeeva O.V.,
Thermodynamic Properties of Polycyclic Aromatic Hydrocarbons in the Gaseous Phase. Institute for High Temperatures, USSR Academy of Sciences, Preprint No.1-238 (in Russian), Moscow, 1988. [all data]
Dorofeeva O.V., 1986
Dorofeeva O.V.,
On calculation of thermodynamic properties of polycyclic aromatic hydrocarbons,
Thermochim. Acta, 1986, 102, 59-66. [all data]
Moiseeva N.F., 1989
Moiseeva N.F.,
Development of Benson group additivity method for estimation of ideal gas thermodynamic properties of polycyclic aromatic hydrocarbons,
Thermochim. Acta, 1989, 153, 77-85. [all data]
Frenkel M., 1994
Frenkel M.,
Thermodynamics of Organic Compounds in the Gas State, Vol. I, II, Thermodynamics Research Center, College Station, Texas, 1994, 1994. [all data]
Smith, 1980
Smith, G.W.,
Phase behavior of some condensed polycyclic aromatics,
Mol. Cryst. Liq. Cryst., 1980, 64, 15. [all data]
Casellato, Vecchi, et al., 1973
Casellato, F.; Vecchi, C.; Girell, A.,
Differential calorimetric study of polycyclic aromatic hydrocarbons,
Thermochim. Acta, 1973, 6, 4, 361, https://doi.org/10.1016/0040-6031(73)87003-0
. [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]
Wakayama and Inokuchi, 1967
Wakayama, N.; Inokuchi, H.,
Heats of sublimation of polycyclic aromatic hydrocarbons and their molecular packings,
Bull. Chem. Soc. Jpn., 1967, 40, 2267. [all data]
Lei, Chankalal, et al., 2002
Lei, Ying Duan; Chankalal, Raymond; Chan, Anita; Wania, Frank,
Supercooled Liquid Vapor Pressures of the Polycyclic Aromatic Hydrocarbons,
J. Chem. Eng. Data, 2002, 47, 4, 801-806, https://doi.org/10.1021/je0155148
. [all data]
Nass, Lenoir, et al., 1995
Nass, Karen; Lenoir, Dieter; Kettrup, Antonius,
Calculation of the Thermodynamic Properties of Polycyclic Aromatic Hydrocarbons by an Incremental Procedure,
Angew. Chem. Int. Ed. Engl., 1995, 34, 16, 1735-1736, https://doi.org/10.1002/anie.199517351
. [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]
Murray, Pottie, et al., 1974
Murray, John James; Pottie, Roswell Francis; Pupp, Christian,
The Vapor Pressures and Enthalpies of Sublimation of Five Polycyclic Aromatic Hydrocarbons,
Can. J. Chem., 1974, 52, 4, 557-563, https://doi.org/10.1139/v74-087
. [all data]
Wakayama and Inokuchi, 1967, 2
Wakayama, Nobuko; Inokuchi, Hiroo,
Heats of Sublimation of Polycyclic Aromatic Hydrocarbons and Their Molecular Packings,
Bull. Chem. Soc. Jpn., 1967, 40, 10, 2267-2271, https://doi.org/10.1246/bcsj.40.2267
. [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]
Meot-Ner (Mautner), 1980
Meot-Ner (Mautner), M.,
Dimer Cations of Polycyclic Aromatics: Experimental Bonding Energies and Resonance Stabilization,
J. Phys. Chem., 1980, 84, 21, 2724, https://doi.org/10.1021/j100458a012
. [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]
Chen and Cooks, 1995
Chen, G.D.; Cooks, R.G.,
Electron affinities of polycyclic aromatic hydrocarbons determined by the kinetic method,
J. Mass Spectrom., 1995, 30, 8, 1167, https://doi.org/10.1002/jms.1190300814
. [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]
Clar and Schmidt, 1977
Clar, E.; Schmidt, W.,
Correlations between photoelectron and ultraviolet absorption spectra of polycyclic hydrocarbons. The perylene, coronene and bisanthene series,
Tetrahedron, 1977, 33, 2093. [all data]
Boschi, Murrell, et al., 1972
Boschi, R.; Murrell, J.N.; Schmidt, W.,
Photoelectron spectra of polycyclic aromatic hydrocarbons,
Faraday Discuss. Chem. Soc., 1972, 54, 116. [all data]
Briegleb, 1964
Briegleb, G.,
Electron affinity of organic molecules,
Angew. Chem. Intern. Ed., 1964, 3, 617. [all data]
Matsen, 1956
Matsen, F.A.,
Electron affinities, methyl affinities, and ionization energies of condensed ring aromatic hydrocarbons,
J. Chem. Phys., 1956, 24, 602. [all data]
Clar and Schmidt, 1976
Clar, E.; Schmidt, W.,
Correlations between photoelectron and phosphorescence spectra of polycyclic hydrocarbons,
Tetrahedron, 1976, 32, 2563. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
Cp,gas Constant pressure heat capacity of gas EA Electron affinity IE (evaluated) Recommended ionization energy T Temperature Tfus Fusion (melting) point ΔfusH Enthalpy of fusion ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔrS° Entropy 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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