(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

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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	52.49	kcal/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	53.36	kcal/mol	Ccb	Marantz and Armstrong, 1968	see Marantz and Armstrong, 1968, 2; ALS
Δ_fH°_gas	53.63	kcal/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

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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	-1759.32 ± 0.12	kcal/mol	Ccb	Yates and McDonald, 1971	Corresponding Δ_fHº_liquid = 32.71 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_solid	31.8 ± 0.2	kcal/mol	Ccb	Lobanov and Karmanova, 1971	ALS
Δ_fH°_solid	32.68	kcal/mol	Ccb	Marantz and Armstrong, 1968	see Marantz and Armstrong, 1968, 2; ALS
Δ_fH°_solid	32.93 ± 0.68	kcal/mol	Ccb	Richardson and Parks, 1939	Reanalyzed by Cox and Pilcher, 1970, Original value = 32.47 kcal/mol; ALS
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_solid	-1758.4 ± 0.2	kcal/mol	Ccb	Lobanov and Karmanova, 1971	Corresponding Δ_fHº_solid = 31.8 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_solid	-1759.28 ± 0.93	kcal/mol	Ccb	Marantz and Armstrong, 1968	see Marantz and Armstrong, 1968, 2; Corresponding Δ_fHº_solid = 32.67 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_solid	-1760.18 ± 0.24	kcal/mol	Ccb	Coops and Hoijtink, 1950	Reanalyzed by Cox and Pilcher, 1970, Original value = -1759. ± 0.12 kcal/mol; Corresponding Δ_fHº_solid = 33.576 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_solid	-1759.53 ± 0.67	kcal/mol	Ccb	Richardson and Parks, 1939	Reanalyzed by Cox and Pilcher, 1970, Original value = -1758.80 kcal/mol; Corresponding Δ_fHº_solid = 32.92 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity	Value	Units	Method	Reference	Comment
S°_{solid,1 bar}	59.03	cal/mol*K	N/A	Van Miltenburg and Bouwstra, 1984	DH

Constant pressure heat capacity of solid

C_p,solid (cal/mol*K)	Temperature (K)	Reference	Comment
60.010	320.	Bouwstra, De Leeuw, et al., 1985	T = 320 to 410 K.; DH
56.17	298.15	Van Miltenburg and Bouwstra, 1984	T = 8 to 350 K.; DH

Phase change data

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Data compiled as indicated in comments:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
BS - Robert L. Brown and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity	Value	Units	Method	Reference	Comment
T_boil	579.55	K	N/A	Lecat, 1943	Uncertainty assigned by TRC = 0.5 K; TRC
Quantity	Value	Units	Method	Reference	Comment
T_fus	396. ± 2.	K	AVG	N/A	Average of 7 values; Individual data points
Quantity	Value	Units	Method	Reference	Comment
T_triple	397.40	K	N/A	Bouwstra, deLeeuw, et al., 1985	Uncertainty assigned by TRC = 0.02 K; TRC
T_triple	398.	K	N/A	van Miltenburg and Bouwstra, 1984	Uncertainty assigned by TRC = 0.5 K; TRC
Quantity	Value	Units	Method	Reference	Comment
Δ_vapH°	19.0	kcal/mol	CGC	Chickos, Hesse, et al., 1998	AC
Δ_vapH°	19.1	kcal/mol	CGC	Chickos, Hosseini, et al., 1995	Based on data from 453. to 503. K.; AC
Δ_vapH°	19.0	kcal/mol	CGC	Chickos, Hosseini, et al., 1995	Based on data from 403. to 453. K.; AC
Quantity	Value	Units	Method	Reference	Comment
Δ_subH°	24. ± 3.	kcal/mol	AVG	N/A	Average of 6 values; Individual data points

Reduced pressure boiling point

T_boil (K)	Pressure (atm)	Reference	Comment
579.2	0.979	Aldrich Chemical Company Inc., 1990	BS
439.7	0.016	Weast and Grasselli, 1989	BS

Enthalpy of vaporization

Δ_vapH (kcal/mol)	Temperature (K)	Method	Reference	Comment
15.7	434.	A	Stephenson and Malanowski, 1987	Based on data from 419. to 580. K.; AC

Enthalpy of sublimation

Δ_subH (kcal/mol)	Temperature (K)	Method	Reference	Comment
23.8	313.	A	Stephenson and Malanowski, 1987	Based on data from 298. to 343. K.; AC
24.81 ± 0.60	315.	N/A	Kratt, Beckhaus, et al., 1983	Based on data from 293. to 338. K.; AC
20.7 ± 0.02	309.	TM	Engelsman, 1955	Based on data from 303. to 315. K.; AC
21.7 ± 0.2	329.	V	Wolf and Weghofer, 1938	ALS

Enthalpy of fusion

Δ_fusH (kcal/mol)	Temperature (K)	Method	Reference	Comment
6.5416	398.	N/A	Van Miltenburg and Bouwstra, 1984	DH
6.55	398.2	N/A	Acree, 1991	AC
6.62	397.4	AC	Bouwstra, Leeuw, et al., 1985	AC

Entropy of fusion

Δ_fusS (cal/mol*K)	Temperature (K)	Reference	Comment
16.4	398.	Van Miltenburg and Bouwstra, 1984	DH

Enthalpy of phase transition

ΔH_trs (kcal/mol)	Temperature (K)	Initial Phase	Final Phase	Reference	Comment
6.6181	397.40	crystaline, I	liquid	Bouwstra, De Leeuw, et al., 1985	DH

Entropy of phase transition

ΔS_trs (cal/mol*K)	Temperature (K)	Initial Phase	Final Phase	Reference	Comment
16.6	397.40	crystaline, I	liquid	Bouwstra, De Leeuw, et al., 1985	DH

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:

Reaction thermochemistry data

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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°	-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

(E)-Stilbene =

By formula: C₁₄H₁₂ = C₁₄H₁₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	8.4 ± 5.6	kcal/mol	Cpha	Herman and Goodman, 1989	solid phase; solvent: Acetonitrile/water
Δ_rH°	4.59 ± 0.09	kcal/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°	-1.2 ± 0.1	kcal/mol	Cm	Bastianelli, Caia, et al., 1991	liquid phase; Thermal Isomerization
Δ_rH°	-2.9 ± 0.3	kcal/mol	Ciso	Fischer, Muszkat, et al., 1968	solid phase; solvent: Cyclohexane

Gas Chromatography

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Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Kovats' RI, non-polar column, custom temperature program

View large format table.

Column type	Active phase	I	Reference	Comment
Packed	SE-30	1755.	Ramsey, Lee, et al., 1980	He, Chromosorb G HP (80-100 mesh); Column length: 1.5 m; Program: not specified

Kovats' RI, polar column, isothermal

View large format table.

Column type	Active phase	Temperature (C)	I	Reference	Comment
Capillary	SP-1000	185.	2547.	Kríz, Popl, et al., 1974	N2; Column length: 50. m; Column diameter: 0.25 mm

Van Den Dool and Kratz RI, non-polar column, temperature ramp

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	SE-52	1686.	Carugno and Rossi, 1967	N2, 1.8 K/min; Column length: 65. m; Column diameter: 0.3 mm; T_start: 100. C; T_end: 300. C

Van Den Dool and Kratz RI, polar column, temperature ramp

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	HP-Innowax	2536.	Adamiec, Rossner, et al., 2001	30. m/0.25 mm/0.25 μm, N2, 5. K/min; T_start: 60. C; T_end: 220. C

Normal alkane RI, non-polar column, custom temperature program

View large format table.

Column type	Active phase	I	Reference	Comment
Other	Methyl Silicone	1755.	Ardrey and Moffat, 1981	Program: not specified

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas Chromatography, 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]

Lecat, 1943
Lecat, M., Azeotropes of Ethyl Urethane and other Azeotropes, C. R. Hebd. Seances Acad. Sci., 1943, 217, 273. [all data]

Bouwstra, deLeeuw, et al., 1985
Bouwstra, J.A.; deLeeuw, V.V.; van Miltenburg, J.C., Properties of mixed-crystalline organic material prepared by zone levelling 4. melting properties and excess enthalpies of (trans-azobenzene + trans-stilbene), J. Chem. Thermodyn., 1985, 17, 685. [all data]

van Miltenburg and Bouwstra, 1984
van Miltenburg, J.C.; Bouwstra, J.A., Thermodynamic properties of trans-azobenzene and trans-stilbene, J. Chem. Thermodyn., 1984, 16, 61-5. [all data]

Chickos, Hesse, et al., 1998
Chickos, James; Hesse, Donald; Hosseini, Sarah; Nichols, Gary; Webb, Paul, Sublimation enthalpies at 298.15K using correlation gas chromatography and differential scanning calorimetry measurements, Thermochimica Acta, 1998, 313, 2, 101-110, https://doi.org/10.1016/S0040-6031(97)00432-2 . [all data]

Chickos, Hosseini, et al., 1995
Chickos, James S.; Hosseini, Sarah; Hesse, Donald G., Determination of vaporization enthalpies of simple organic molecules by correlations of changes in gas chromatographic net retention times, Thermochimica Acta, 1995, 249, 41-62, https://doi.org/10.1016/0040-6031(95)90670-3 . [all data]

Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc., Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]

Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [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]

Kratt, Beckhaus, et al., 1983
Kratt, G.; Beckhaus, H.D.; Bernioehr, W.; Ruechardt, C., Thermolabile hydrocarbons. XVII. Enthalpies of combustion and formation of ten sym-tetraalkyl-1,2-diarylethanes, Thermochim. Acta, 1983, 62, 279-294. [all data]

Engelsman, 1955
Engelsman, J.J., , Ph.D. Thesis, Vrije Universiteit Te Amsterdam, 1955. [all data]

Wolf and Weghofer, 1938
Wolf, K.L.; Weghofer, H., Uber sublimationswarmen, Z. Phys. Chem., 1938, 39, 194-208. [all data]

Acree, 1991
Acree, William E., Thermodynamic properties of organic compounds: enthalpy of fusion and melting point temperature compilation, Thermochimica Acta, 1991, 189, 1, 37-56, https://doi.org/10.1016/0040-6031(91)87098-H . [all data]

Bouwstra, Leeuw, et al., 1985
Bouwstra, J.A.; Leeuw, V.V. de; Miltenburg, J.C. van, Properties of mixed-crystalline organic material prepared by zone levelling IV. Melting properties and excess enthalpies of (trans-azobenzene + trans-stilbene), The Journal of Chemical Thermodynamics, 1985, 17, 7, 685-695, https://doi.org/10.1016/0021-9614(85)90123-5 . [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]

Ramsey, Lee, et al., 1980
Ramsey, J.D.; Lee, T.D.; Osselton, M.D.; Moffat, A.C., Gas-liquid chromatographic retention indices of 296 non-drug substances on SE-30 or OV-1 likely to be encountered in toxicological analyses, J. Chromatogr., 1980, 184, 2, 185-206, https://doi.org/10.1016/S0021-9673(00)85641-1 . [all data]

Kríz, Popl, et al., 1974
Kríz, J.; Popl, M.; Mostecký, J., Retention indices of biphenyls and diphenylalkanes, J. Chromatogr., 1974, 97, 1, 3-13, https://doi.org/10.1016/S0021-9673(01)97577-6 . [all data]

Carugno and Rossi, 1967
Carugno, N.; Rossi, S., Evaluation of polynuclear hydrocarbons in cigarette smoke by glass capillary columns, J. Gas Chromatogr., 1967, 5, 2, 103-106, https://doi.org/10.1093/chromsci/5.2.103 . [all data]

Adamiec, Rossner, et al., 2001
Adamiec, J.; Rossner, J.; Velisek, J.; Cejpek, K.; Savel, J., Minor Strecker degradation products of phenylalanine and phenylglycine, Eur. Food Res. Technol., 2001, 212, 2, 135-140, https://doi.org/10.1007/s002170000234 . [all data]

Ardrey and Moffat, 1981
Ardrey, R.E.; Moffat, A.C., Gas-liquid chromatographic retention indices of 1318 substances of toxicological interest on SE-30 or OV-1 stationary phase, J. Chromatogr., 1981, 220, 3, 195-252, https://doi.org/10.1016/S0021-9673(00)81925-1 . [all data]

Notes

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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)
T_boil	Boiling point
T_fus	Fusion (melting) point
T_triple	Triple point temperature
ΔH_trs	Enthalpy of phase transition
ΔS_trs	Entropy of phase transition
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_fusH	Enthalpy of fusion
Δ_fusS	Entropy of fusion
Δ_rH°	Enthalpy of reaction at standard conditions
Δ_subH	Enthalpy of sublimation
Δ_subH°	Enthalpy of sublimation at standard conditions
Δ_vapH	Enthalpy of vaporization
Δ_vapH°	Enthalpy of vaporization at standard conditions

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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