Acenaphthene
- Formula: C12H10
- Molecular weight: 154.2078
- IUPAC Standard InChIKey: CWRYPZZKDGJXCA-UHFFFAOYSA-N
- CAS Registry Number: 83-32-9
- 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. - Isotopologues:
- Other names: Acenaphthylene, 1,2-dihydro-; Peri-Ethylenenaphthalene; Naphthyleneethylene; 1,2-Dihydroacenaphthylene; 1,8-Ethylenenaphthalene; Acenaphtene
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Gas phase thermochemistry data
Go To: Top, Gas phase ion energetics data, Ion clustering data, IR Spectrum, UV/Visible 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:
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | 156.8 ± 3.1 | kJ/mol | Review | Roux, Temprado, et al., 2008 | There are sufficient literature values to make a qualified recommendation where the suggested value is in good agreement with values predicted using thermochemical cycles or from reliable estimates. In general, the evaluated uncertainty limits are on the order of (2 to 4) kJ/mol.; DRB |
ΔfH°gas | 156. ± 4. | kJ/mol | Ccb | Boyd, Christensen, et al., 1965 | ALS |
Constant pressure heat capacity of gas
Cp,gas (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
38.72 | 50. | Dorofeeva O.V., 1989 | GT |
55.21 | 100. | ||
77.31 | 150. | ||
103.81 | 200. | ||
147.01 | 273.15 | ||
162.2 ± 1.0 | 298.15 | ||
163.27 | 300. | ||
220.85 | 400. | ||
269.56 | 500. | ||
308.84 | 600. | ||
340.46 | 700. | ||
366.25 | 800. | ||
387.56 | 900. | ||
405.37 | 1000. | ||
420.36 | 1100. | ||
433.08 | 1200. | ||
443.92 | 1300. | ||
453.21 | 1400. | ||
461.21 | 1500. |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Ion clustering data, IR Spectrum, UV/Visible 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
L - 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
View reactions leading to C12H10+ (ion structure unspecified)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 7.75 ± 0.05 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 851.7 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 821.0 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Proton affinity at 298K
Proton affinity (kJ/mol) | Reference | Comment |
---|---|---|
849.8 | 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 |
---|---|---|
821.7 | 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 |
---|---|---|---|
7.68 ± 0.05 | EQ | Mautner(Meot-Ner), 1980 | LLK |
7.73 ± 0.01 | PE | Dewar, Haselbach, et al., 1970 | RDSH |
7.66 | CTS | Kinoshita, 1962 | RDSH |
7.76 ± 0.03 | PE | Heilbronner, Hoshi, et al., 1976 | Vertical value; LLK |
7.82 ± 0.04 | PE | Boschi, Clar, et al., 1974 | Vertical value; LLK |
De-protonation reactions
C12H9- + =
By formula: C12H9- + H+ = C12H10
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1559. ± 10. | kJ/mol | TDEq | Meot-ner and Kafafi, 1988 | gas phase; acenaphthene: 1,8-(1,2-ethano)naphthalene; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1531. ± 8.4 | kJ/mol | TDEq | Meot-ner and Kafafi, 1988 | gas phase; acenaphthene: 1,8-(1,2-ethano)naphthalene; B |
Ion clustering 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 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. Searches may be limited to ion clustering reactions. A general reaction search form is also available.
Clustering reactions
By formula: C6H7N+ + C12H10 = (C6H7N+ • C12H10)
Bond type: Charge transfer bond (positive ion)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 73.2 | kJ/mol | PHPMS | Meot-Ner (Mautner) and El-Shall, 1986 | gas phase |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 115. | J/mol*K | PHPMS | Meot-Ner (Mautner) and El-Shall, 1986 | gas phase |
By formula: C12H8+ + C12H10 = (C12H8+ • C12H10)
Bond type: Charge transfer bond (positive ion)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 59.4 | 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 |
---|---|---|---|---|
26. | 283. | PHPMS | Meot-Ner (Mautner), 1980 | gas phase; Entropy change calculated or estimated |
By formula: C12H10+ + C12H10 = (C12H10+ • C12H10)
Bond type: Charge transfer bond (positive ion)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 71.1 | 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 |
---|---|---|---|---|
34. | 283. | PHPMS | Meot-Ner (Mautner), 1980 | gas phase; Entropy change calculated or estimated |
By formula: C12H11+ + C12H10 = (C12H11+ • C12H10)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 61.9 | 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 |
---|---|---|---|---|
23. | 330. | PHPMS | Meot-Ner (Mautner), 1980 | gas phase; Entropy change calculated or estimated |
IR Spectrum
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, Ion clustering data, UV/Visible spectrum, References, Notes
Data compiled by: Coblentz Society, Inc.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
UV/Visible spectrum
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, Ion clustering 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 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 | Herington and Jones, 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. 599 |
Instrument | Beckman spectrophotometer |
Melting point | 93.4 |
Boiling point | 279 |
References
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, UV/Visible spectrum, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Roux, Temprado, et al., 2008
Roux, M.V.; Temprado, M.; Chickos, J.S.; Nagano, Y.,
Critically Evaluated Thermochemical Properties of Polycyclic Aromatic Hydrocarbons,
J. Phys. Chem. Ref. Data, 2008, 37, 4, 1855-1996. [all data]
Boyd, Christensen, et al., 1965
Boyd, R.H.; Christensen, R.L.; Pua, R.,
The heats of combustion of acenaphthene, acenaphthylene, and fluoranthene. Strain and delocalization in bridged naphthalenes,
J. Am. Chem. Soc., 1965, 87, 3554-3559. [all data]
Dorofeeva O.V., 1989
Dorofeeva O.V.,
Thermodynamic Properties of Gaseous Polycyclic Aromatic Hydrocarbons Containing Five-Membered Rings. Institute for High Temperatures, USSR Academy of Sciences, Preprint No.1-263 (in Russian), Moscow, 1989. [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]
Dewar, Haselbach, et al., 1970
Dewar, M.J.S.; Haselbach, E.; Worley, S.D.,
Calculated and observed ionization potentials of unsaturated polycyclic hydrocarbons; calculated heats of formation by several semiempirical s.c.f. m.o. methods,
Proc. Roy. Soc. (London), 1970, A315, 431. [all data]
Kinoshita, 1962
Kinoshita, M.,
The absorption spectra of the molecular complexes of aromatic compounds with p-bromanil,
Bull. Chem. Soc. Japan, 1962, 35, 1609. [all data]
Heilbronner, Hoshi, et al., 1976
Heilbronner, E.; Hoshi, T.; von Rosenberg, J.L.; Hafner, K.,
Alkyl-induced, natural hypsochromic shifts of the 2A←2X and 2B←2X transitions of azulene and naphthalene radical cations,
Nouv. J. Chim., 1976, 1, 105. [all data]
Boschi, Clar, et al., 1974
Boschi, R.; Clar, E.; Schmidt, W.,
Photoelectron spectra of polynuclear aromatics. III. The effect of nonplanarity in sterically overcrowded aromatic hydrocarbons,
J. Chem. Phys., 1974, 60, 4406. [all data]
Meot-ner and Kafafi, 1988
Meot-ner, M.; Kafafi, S.A.,
Carbon Acidities of Aromatic Compounds,
J. Am. Chem. Soc., 1988, 110, 19, 6297, https://doi.org/10.1021/ja00227a003
. [all data]
Meot-Ner (Mautner) and El-Shall, 1986
Meot-Ner (Mautner), M.; El-Shall, M.S.,
Ionic Charge Transfer Complexes. 1. Cationic Complexes with Delocalized and Partially Localized pi Systems,
J. Am. Chem. Soc., 1986, 108, 15, 4386, https://doi.org/10.1021/ja00275a026
. [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]
Herington and Jones, 1949
Herington, E.F.G.; Jones, J.I.,
Ultraviolet absorption spectra of some copolymers containing acenaphthylene, and of related compounds,
J. Polym. Sci., 1949, 4, 725-733. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, UV/Visible spectrum, References
- Symbols used in this document:
Cp,gas Constant pressure heat capacity of gas IE (evaluated) Recommended ionization energy T Temperature ΔfH°gas Enthalpy of formation of gas at standard conditions ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔrS° Entropy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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