Acenaphthylene
- Formula: C12H8
- Molecular weight: 152.1919
- IUPAC Standard InChI: InChI=1S/C12H8/c1-3-9-4-2-6-11-8-7-10(5-1)12(9)11/h1-8H
- IUPAC Standard InChIKey: HXGDTGSAIMULJN-UHFFFAOYSA-N
- CAS Registry Number: 208-96-8
- 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: Cyclopenta[de]naphthalene; Acenaphthalene
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Gas phase 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:
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 | 62.91 ± 0.88 | kcal/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 | 63.10 | kcal/mol | N/A | Sadowska, 1966 | Value computed using ΔfHsolid° value of 193.0±4.0 kj/mol from Sadowska, 1966 and ΔsubH° value of 71.0 kj/mol from Boyd, Christensen, et al., 1965.; DRB |
| ΔfH°gas | 61.7 ± 1.4 | kcal/mol | Ccb | Boyd, Christensen, et al., 1965 | ALS |
Constant pressure heat capacity of gas
| Cp,gas (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 8.454 | 50. | Dorofeeva O.V., 1989 | These statistically calculated values were obtained using force field approximation for polycyclic aromatic hydrocarbons to estimate the needed vibrational frequencies (see also [ Dorofeeva O.V., 1986, Moiseeva N.F., 1990]). These functions are reproduced in the reference book [ Frenkel M., 1994].; GT |
| 11.92 | 100. | ||
| 17.23 | 150. | ||
| 23.60 | 200. | ||
| 33.592 | 273.15 | ||
| 36.99 ± 0.24 | 298.15 | ||
| 37.242 | 300. | ||
| 49.885 | 400. | ||
| 60.390 | 500. | ||
| 68.781 | 600. | ||
| 75.488 | 700. | ||
| 80.920 | 800. | ||
| 85.385 | 900. | ||
| 89.097 | 1000. | ||
| 92.213 | 1100. | ||
| 94.847 | 1200. | ||
| 97.089 | 1300. | ||
| 99.008 | 1400. | ||
| 100.66 | 1500. |
Condensed phase 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:
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°solid | 45.60 ± 0.84 | kcal/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°solid | 46.1 ± 1. | kcal/mol | Ccb | Sadowska, 1966 | ALS |
| ΔfH°solid | 44.7 ± 1.1 | kcal/mol | Ccb | Boyd, Christensen, et al., 1965 | ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°solid | -1448. ± 1. | kcal/mol | Ccb | Sadowska, 1966 | Corresponding ΔfHºsolid = 46.1 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°solid | -1446.5 ± 1.1 | kcal/mol | Ccb | Boyd, Christensen, et al., 1965 | Corresponding ΔfHºsolid = 44.6 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
Constant pressure heat capacity of solid
| Cp,solid (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 39.77 | 298. | Sadowska, Stepniewska, et al., 1969 | T = 20 to 89°C, equation only; liquid 90 to 150°C, equation only.; DH |
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 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: C6H7N+ + C12H8 = (C6H7N+ • C12H8)
Bond type: Charge transfer bond (positive ion)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 17.2 | kcal/mol | PHPMS | Meot-Ner (Mautner) and El-Shall, 1986 | gas phase; Entropy change calculated or estimated |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrS° | 26. | cal/mol*K | N/A | Meot-Ner (Mautner) and El-Shall, 1986 | gas phase; Entropy change calculated or estimated |
Free energy of reaction
| ΔrG° (kcal/mol) | T (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 8.7 | 325. | PHPMS | Meot-Ner (Mautner) and El-Shall, 1986 | gas phase; Entropy change calculated or estimated |
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:
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
View reactions leading to C12H8+ (ion structure unspecified)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| IE (evaluated) | 8.12 ± 0.10 | eV | N/A | N/A | L |
Electron affinity determinations
| EA (eV) | Method | Reference | Comment |
|---|---|---|---|
| <0.403 ± 0.026 | ECD | Wojnarovits and Foldiak, 1981 | G3MP2B3 calculations indicate an EA of ca. 0.7 eV; B |
Proton affinity at 298K
| Proton affinity (kcal/mol) | Reference | Comment |
|---|---|---|
| 205.8 | 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) (kcal/mol) | Reference | Comment |
|---|---|---|
| 199.0 | 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 |
|---|---|---|---|
| 8.22 ± 0.04 | PE | Boschi, Clar, et al., 1974 | LLK |
| 8.02 ± 0.01 | PE | Dewar, Haselbach, et al., 1970 | RDSH |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry 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.
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]
Sadowska, 1966
Sadowska, K.W.,
Cieplo tworzenia i uwodornienia acenaftylenu,
Przem. Chem., 1966, 45, 66-67. [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]
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., 1990
Moiseeva N.F.,
Group additivity scheme for calculating the chemical thermodynamic properties of gaseous polycyclic aromatic hydrocarbons containing five-membered rings,
Thermochim. Acta, 1990, 168, 179-186. [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]
Sadowska, Stepniewska, et al., 1969
Sadowska, K.W.; Stepniewska, G.B.; Recko, W.M.,
Specific heat and enthalpy of fusion of acenaphthene and acenaphthylene,
Przem. Chem., 1969, 48, 282-285. [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]
Wojnarovits and Foldiak, 1981
Wojnarovits, L.; Foldiak, G.,
Electron capture detection of aromatic hydrocarbons,
J. Chromatogr. Sci., 1981, 206, 511. [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]
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]
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]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
Cp,gas Constant pressure heat capacity of gas Cp,solid Constant pressure heat capacity of solid EA Electron affinity IE (evaluated) Recommended ionization energy T Temperature ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°solid Enthalpy of formation of solid 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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