(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
The 3d structure may be viewed using Java or Javascript.
Stereoisomers:
- Stilbene
- cis-Stilbene
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, Condensed phase thermochemistry data, Reaction thermochemistry data, References, Notes

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
Δ_fH°_gas	219.6	kJ/mol	N/A	Lobanov and Karmanova, 1971	Value computed using Δ_fH_solid° value of 133.0±0.8 kj/mol from Lobanov and Karmanova, 1971 and Δ_subH° value of 86.6 kj/mol from Marantz and Armstrong, 1968.; DRB
Δ_fH°_gas	223.3	kJ/mol	Ccb	Marantz and Armstrong, 1968	see Marantz and Armstrong, 1968, 2; ALS
Δ_fH°_gas	224.4	kJ/mol	N/A	Richardson and Parks, 1939	Value computed using Δ_fH_solid° value of 137.8±2.8 kj/mol from Richardson and Parks, 1939 and Δ_subH° value of 86.6 kj/mol from Marantz and Armstrong, 1968.; DRB

Condensed phase thermochemistry data

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, References, Notes

Data compiled as indicated in comments:
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
Δ_cH°_liquid	-7360.99 ± 0.50	kJ/mol	Ccb	Yates and McDonald, 1971	Corresponding Δ_fHº_liquid = 136.9 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_solid	133. ± 0.8	kJ/mol	Ccb	Lobanov and Karmanova, 1971	ALS
Δ_fH°_solid	136.7	kJ/mol	Ccb	Marantz and Armstrong, 1968	see Marantz and Armstrong, 1968, 2; ALS
Δ_fH°_solid	137.8 ± 2.8	kJ/mol	Ccb	Richardson and Parks, 1939	Reanalyzed by Cox and Pilcher, 1970, Original value = 135.9 kJ/mol; ALS
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_solid	-7357.1 ± 0.8	kJ/mol	Ccb	Lobanov and Karmanova, 1971	Corresponding Δ_fHº_solid = 133. kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_solid	-7360.8 ± 3.9	kJ/mol	Ccb	Marantz and Armstrong, 1968	see Marantz and Armstrong, 1968, 2; Corresponding Δ_fHº_solid = 136.7 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_solid	-7364.6 ± 1.0	kJ/mol	Ccb	Coops and Hoijtink, 1950	Reanalyzed by Cox and Pilcher, 1970, Original value = -7361. ± 0.51 kJ/mol; Corresponding Δ_fHº_solid = 140.48 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_solid	-7361.9 ± 2.8	kJ/mol	Ccb	Richardson and Parks, 1939	Reanalyzed by Cox and Pilcher, 1970, Original value = -7358.82 kJ/mol; Corresponding Δ_fHº_solid = 137.7 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity	Value	Units	Method	Reference	Comment
S°_{solid,1 bar}	247.0	J/mol*K	N/A	Van Miltenburg and Bouwstra, 1984	DH

Constant pressure heat capacity of solid

C_p,solid (J/mol*K)	Temperature (K)	Reference	Comment
251.08	320.	Bouwstra, De Leeuw, et al., 1985	T = 320 to 410 K.; DH
235.0	298.15	Van Miltenburg and Bouwstra, 1984	T = 8 to 350 K.; DH

Reaction thermochemistry data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, References, Notes

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

(E)-Stilbene + =

By formula: C₁₄H₁₂ + H₂ = C₁₄H₁₄

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-77.78 ± 0.84	kJ/mol	Chyd	Williams, 1942	liquid phase; solvent: Acetic acid; Reanalyzed by Cox and Pilcher, 1970, Original value = -84.2 ± 1.5 kJ/mol; At 302 K

(E)-Stilbene =

By formula: C₁₄H₁₂ = C₁₄H₁₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	35. ± 23.	kJ/mol	Cpha	Herman and Goodman, 1989	solid phase; solvent: Acetonitrile/water
Δ_rH°	19.2 ± 0.4	kJ/mol	Ciso	Saltiel, Ganapathy, et al., 1987	gas phase; At 303.2-461.2 K

= (E)-Stilbene

By formula: C₁₄H₁₂ = C₁₄H₁₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-5.0 ± 0.4	kJ/mol	Cm	Bastianelli, Caia, et al., 1991	liquid phase; Thermal Isomerization
Δ_rH°	-12. ± 1.	kJ/mol	Ciso	Fischer, Muszkat, et al., 1968	solid phase; solvent: Cyclohexane

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Notes

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]

Yates and McDonald, 1971
Yates, K.; McDonald, R.S., A thermochemical probe into the mechanism of electrophilic addition to olefins, J. Am. Chem. Soc., 1971, 93, 6297-6299. [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]

Coops and Hoijtink, 1950
Coops, J.; Hoijtink, G.J., Thermochemical investigations on arylethenes. I. Heats of combustion of phenylethenes, Recl. Trav. Chim. Pays-Bas, 1950, 69, 358-367. [all data]

Van Miltenburg and Bouwstra, 1984
Van Miltenburg, J.C.; Bouwstra, J.A., Thermodynamic properties of trans-azobenzene and trans-stilbene, J. Chem. Thermodynam., 1984, 16, 61-65. [all data]

Bouwstra, De Leeuw, et al., 1985
Bouwstra, J.A.; De Leeuw, V.V.; Van Miltenburg, J.C., Properties of mixed-crystalline organic material prepared by zone levelling. IV. Melting properties and excess enthalpies of (trans-azobenzene + trans-stilbene), J. Chem. Thermodynam., 1985, 17, 685-695. [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]

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, Condensed phase thermochemistry data, Reaction thermochemistry data, References

Symbols used in this document:

C_p,solid	Constant pressure heat capacity of solid
S°_{solid,1 bar}	Entropy of solid at standard conditions (1 bar)
Δ_cH°_liquid	Enthalpy of combustion of liquid at standard conditions
Δ_cH°_solid	Enthalpy of combustion of solid at standard conditions
Δ_fH°_gas	Enthalpy of formation of gas at standard conditions
Δ_fH°_solid	Enthalpy of formation of solid at standard conditions
Δ_rH°	Enthalpy of reaction at standard conditions

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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