(E)-Stilbene
- Formula: C14H12
- Molecular weight: 180.2451
- IUPAC Standard InChI: InChI=1S/C14H12/c1-3-7-13(8-4-1)11-12-14-9-5-2-6-10-14/h1-12H/b12-11+
- IUPAC Standard InChIKey: PJANXHGTPQOBST-VAWYXSNFSA-N
- CAS Registry Number: 103-30-0
- Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
View 3d structure (requires JavaScript / HTML 5) - Stereoisomers:
- Other names: Benzene, 1,1'-(1,2-ethenediyl)bis-, (E)-; Stilbene, (E)-; (E)-1,2-Diphenylethylene; trans-α,β-Diphenylethylene; trans-Stilbene; trans-1,2-Diphenylethene; trans-1,2-Diphenylethylene; (E)-1,2-Diphenylethene; Dibenzal, (E)-; Dibenzylidne, (E)-; 1,2-Diphenylethylene (trans); (1,2-Ethenediyl)-1,1'-bisbenzene, (E)-; Stilbene (trans); 1,trans-2-Diphenylethene; 1,trans-2-Diphenylethylene; trans-Diphenylethene; 1,2-Diphenylethene, (E)-; 1,1'-(1,2-Ethanediyl)bis[benzene], trans; Toluylene; t-Stilbene; trans-Bibenzal; trans-Bibenzylidene; Benzene, 1,1'-(1E)-1,2-ethenediylbis-; NSC 2069; 1,1'-(1,2-Ethanediyl)bis(benzene), (E)-
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Gas phase thermochemistry data
Go To: Top, 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 compiled as indicated in comments:
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | 52.49 | kcal/mol | N/A | Lobanov and Karmanova, 1971 | Value computed using ΔfHsolid° value of 133.0±0.8 kj/mol from Lobanov and Karmanova, 1971 and ΔsubH° value of 86.6 kj/mol from Marantz and Armstrong, 1968.; DRB |
| ΔfH°gas | 53.36 | kcal/mol | Ccb | Marantz and Armstrong, 1968 | see Marantz and Armstrong, 1968, 2; ALS |
| ΔfH°gas | 53.63 | kcal/mol | N/A | Richardson and Parks, 1939 | Value computed using ΔfHsolid° value of 137.8±2.8 kj/mol from Richardson and Parks, 1939 and ΔsubH° value of 86.6 kj/mol from Marantz and Armstrong, 1968.; DRB |
Reaction thermochemistry data
Go To: Top, Gas phase 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 compiled by: 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
+
=
By formula: C14H12 + H2 = C14H14
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -18.59 ± 0.20 | kcal/mol | Chyd | Williams, 1942 | liquid phase; solvent: Acetic acid; Reanalyzed by Cox and Pilcher, 1970, Original value = -20.14 ± 0.36 kcal/mol; At 302 K |
=
By formula: C14H12 = C14H12
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 8.4 ± 5.6 | kcal/mol | Cpha | Herman and Goodman, 1989 | solid phase; solvent: Acetonitrile/water |
| ΔrH° | 4.59 ± 0.09 | kcal/mol | Ciso | Saltiel, Ganapathy, et al., 1987 | gas phase; At 303.2-461.2 K |
=
By formula: C14H12 = C14H12
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -1.2 ± 0.1 | kcal/mol | Cm | Bastianelli, Caia, et al., 1991 | liquid phase; Thermal Isomerization |
| ΔrH° | -2.9 ± 0.3 | kcal/mol | Ciso | Fischer, Muszkat, et al., 1968 | solid phase; solvent: Cyclohexane |
References
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Lobanov and Karmanova, 1971
Lobanov, G.A.; Karmanova, L.P.,
Enthalpy of formation of some organic substances,
Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol., 1971, 14, 865-867. [all data]
Marantz and Armstrong, 1968
Marantz, S.; Armstrong, G.T.,
Heats of combustion of trans-stilbene and trans-2,2',4,',6,6'-hexanitrostilbene (HNS) (Correction),
J. Chem. Eng. Data, 1968, 13, 455. [all data]
Marantz and Armstrong, 1968, 2
Marantz, S.; Armstrong, G.T.,
Heats of combustion of trans-stilbene and trans-2,2',4,4',6,6'-hexanitrostilbene (HNS),
J. Chem. Eng. Data, 1968, 13, 118-121. [all data]
Richardson and Parks, 1939
Richardson, J.W.; Parks, G.S.,
Thermal data on organic compounds. XIX. Modern combustion data for some non-volatile compounds containing carbon, hydrogen and oxygen,
J. Am. Chem. Soc., 1939, 61, 3543-3546. [all data]
Williams, 1942
Williams, R.B.,
Heats of catalytic hydrogenation in solution. I. Apparatus, technique, and the heats of hydrogenation of certain pairs of stereoisomers,
J. Am. Chem. Soc., 1942, 64, 1395-1404. [all data]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]
Herman and Goodman, 1989
Herman, M.S.; Goodman, J.L.,
Determination of the enthalpy and reaction volume changes of organic photoreactions using photoacoustic calorimetry,
J. Am. Chem. Soc., 1989, 111, 1849-1854. [all data]
Saltiel, Ganapathy, et al., 1987
Saltiel, J.; Ganapathy, S.; Werking, C.,
The ΔH for thermal trans-stilbene/cis-stilbene isomerization. Do S0 and T1 potential energy curves cross?,
J. Phys. Chem., 1987, 91, 2755-2758. [all data]
Bastianelli, Caia, et al., 1991
Bastianelli, C.; Caia, V.; Cum, G.; Gallo, R.; Mancini, V.,
Thermal isomerization of photochemically synthesized (Z)-9-styrylacridines. An unusually high enthalpy of Z->E conversion for stilbene-like compounds,
J. Chem. Soc. Perkin Trans. 2, 1991, 679-683. [all data]
Fischer, Muszkat, et al., 1968
Fischer, G.; Muszkat, K.A.; Fischer, E.,
Thermodynamic equilibrium between cis- and trans-isomers in stilbene and some derivatives,
J. Chem. Soc. B, 1968, 1156-1158. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, References
- Symbols used in this document:
ΔfH°gas Enthalpy of formation of gas at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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