Acenaphthylene
- Formula: C12H8
- Molecular weight: 152.1919
- 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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Phase change data
Go To: Top, 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:
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
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 |
---|---|---|---|---|---|
Tboil | 553.2 | K | N/A | Aldrich Chemical Company Inc., 1990 | BS |
Tboil | 538. to 548. | K | N/A | Buckingham and Donaghy, 1982 | BS |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 365. to 366. | K | N/A | Buckingham and Donaghy, 1982 | BS |
Tfus | 362.6 | K | N/A | Sadowska, Stepniewska, et al., 1969 | Uncertainty assigned by TRC = 0.2 K; TRC |
Tfus | 366.4 | K | N/A | Boyd, Christensen, et al., 1965 | Uncertainty assigned by TRC = 0.3 K; TRC |
Tfus | 365.7 | K | N/A | Sangster and Irvine, 1956 | Uncertainty assigned by TRC = 2. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 64.6 ± 5.8 | kJ/mol | CGC | Roux, Temprado, et al., 2008 | AC |
ΔvapH° | 69.1 ± 2.2 | kJ/mol | GC | Haftka, Parsons, et al., 2006 | AC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 72. ± 2. | kJ/mol | AVG | N/A | Average of 6 values; Individual data points |
Reduced pressure boiling point
Tboil (K) | Pressure (bar) | Reference | Comment |
---|---|---|---|
429. to 433. | 0.037 | Buckingham and Donaghy, 1982 | BS |
Enthalpy of sublimation
ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
77.2 | 383. | GS | Nass, Lenoir, et al., 1995 | Based on data from 313. to 453. K.; AC |
73.2 ± 0.5 | 303. | GS | Sonnefeld, Zoller, et al., 1983 | Based on data from 238. to 323. K.; AC |
71.1 ± 1.3 | 286. to 318. | A | Cox and Pilcher, 1970 | See also Stephenson and Malanowski, 1987 and Boyd, Christensen, et al., 1965, 2.; AC |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
10.96 | 362. | Domalski and Hearing, 1996 | See also Cheda and Westrum, 1994.; AC |
6.940 | 362.6 | Sadowska, Stepniewska, et al., 1969, 2 | DH |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
19.14 | 362.6 | Sadowska, Stepniewska, et al., 1969, 2 | DH |
Gas phase ion energetics data
Go To: Top, Phase change 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:
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 (kJ/mol) | Reference | Comment |
---|---|---|
861.1 | 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 |
---|---|---|
832.6 | 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 |
---|---|---|---|
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, Phase change 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.
Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc.,
Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]
Buckingham and Donaghy, 1982
Buckingham, J.; Donaghy, S.M.,
Dictionary of Organic Compounds: Fifth Edition, Chapman and Hall, New York, 1982, 1. [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. [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. [all data]
Sangster and Irvine, 1956
Sangster, R.C.; Irvine, J.W.,
Study of Organic Scintillators,
J. Chem. Phys., 1956, 24, 670. [all data]
Roux, Temprado, et al., 2008
Roux, Maria Victoria; Temprado, Manuel; Chickos, James S.; Nagano, Yatsuhisa,
Critically Evaluated Thermochemical Properties of Polycyclic Aromatic Hydrocarbons,
J. Phys. Chem. Ref. Data, 2008, 37, 4, 1855, https://doi.org/10.1063/1.2955570
. [all data]
Haftka, Parsons, et al., 2006
Haftka, Joris J.H.; Parsons, John R.; Govers, Harrie A.J.,
Supercooled liquid vapour pressures and related thermodynamic properties of polycyclic aromatic hydrocarbons determined by gas chromatography,
Journal of Chromatography A, 2006, 1135, 1, 91-100, https://doi.org/10.1016/j.chroma.2006.09.050
. [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]
Sonnefeld, Zoller, et al., 1983
Sonnefeld, W.J.; Zoller, W.H.; May, W.E.,
Dynamic coupled-column liquid-chromatographic determination of ambient-temperature vapor pressures of polynuclear aromatic hydrocarbons,
Anal. Chem., 1983, 55, 2, 275-280, https://doi.org/10.1021/ac00253a022
. [all data]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press Inc., London, 1970, 643. [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]
Boyd, Christensen, et al., 1965, 2
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]
Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D.,
Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III,
J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985
. [all data]
Cheda and Westrum, 1994
Cheda, J.A.R.; Westrum, E.F., Jr.,
Subambient-temperature thermophysics of acenaphthene and acenaphthylene: molecular disorder in the latter,
J. Phys. Chem., 1994, 98, 2482-2488. [all data]
Sadowska, Stepniewska, et al., 1969, 2
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]
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, Phase change data, Gas phase ion energetics data, References
- Symbols used in this document:
EA Electron affinity IE (evaluated) Recommended ionization energy Tboil Boiling point Tfus Fusion (melting) point ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔsubH Enthalpy of sublimation ΔsubH° Enthalpy of sublimation at standard conditions ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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