(E)-Stilbene

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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

Quantity Value Units Method Reference Comment
Δfgas52.49kcal/molN/ALobanov and Karmanova, 1971Value 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
Δfgas53.36kcal/molCcbMarantz and Armstrong, 1968see Marantz and Armstrong, 1968, 2; ALS
Δfgas53.63kcal/molN/ARichardson and Parks, 1939Value 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

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:
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
Δcliquid-1759.32 ± 0.12kcal/molCcbYates and McDonald, 1971Corresponding Δfliquid = 32.71 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
Δfsolid31.8 ± 0.2kcal/molCcbLobanov and Karmanova, 1971ALS
Δfsolid32.68kcal/molCcbMarantz and Armstrong, 1968see Marantz and Armstrong, 1968, 2; ALS
Δfsolid32.93 ± 0.68kcal/molCcbRichardson and Parks, 1939Reanalyzed by Cox and Pilcher, 1970, Original value = 32.47 kcal/mol; ALS
Quantity Value Units Method Reference Comment
Δcsolid-1758.4 ± 0.2kcal/molCcbLobanov and Karmanova, 1971Corresponding Δfsolid = 31.8 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δcsolid-1759.28 ± 0.93kcal/molCcbMarantz and Armstrong, 1968see Marantz and Armstrong, 1968, 2; Corresponding Δfsolid = 32.67 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δcsolid-1760.18 ± 0.24kcal/molCcbCoops and Hoijtink, 1950Reanalyzed by Cox and Pilcher, 1970, Original value = -1759. ± 0.12 kcal/mol; Corresponding Δfsolid = 33.576 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δcsolid-1759.53 ± 0.67kcal/molCcbRichardson and Parks, 1939Reanalyzed by Cox and Pilcher, 1970, Original value = -1758.80 kcal/mol; Corresponding Δfsolid = 32.92 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
solid,1 bar59.03cal/mol*KN/AVan Miltenburg and Bouwstra, 1984DH

Constant pressure heat capacity of solid

Cp,solid (cal/mol*K) Temperature (K) Reference Comment
60.010320.Bouwstra, De Leeuw, et al., 1985T = 320 to 410 K.; DH
56.17298.15Van Miltenburg and Bouwstra, 1984T = 8 to 350 K.; DH

Phase change 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:
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
Tboil579.55KN/ALecat, 1943Uncertainty assigned by TRC = 0.5 K; TRC
Quantity Value Units Method Reference Comment
Tfus396. ± 2.KAVGN/AAverage of 7 values; Individual data points
Quantity Value Units Method Reference Comment
Ttriple397.40KN/ABouwstra, deLeeuw, et al., 1985Uncertainty assigned by TRC = 0.02 K; TRC
Ttriple398.KN/Avan Miltenburg and Bouwstra, 1984Uncertainty assigned by TRC = 0.5 K; TRC
Quantity Value Units Method Reference Comment
Δvap19.0kcal/molCGCChickos, Hesse, et al., 1998AC
Δvap19.1kcal/molCGCChickos, Hosseini, et al., 1995Based on data from 453. to 503. K.; AC
Δvap19.0kcal/molCGCChickos, Hosseini, et al., 1995Based on data from 403. to 453. K.; AC
Quantity Value Units Method Reference Comment
Δsub24. ± 3.kcal/molAVGN/AAverage of 6 values; Individual data points

Reduced pressure boiling point

Tboil (K) Pressure (atm) Reference Comment
579.20.979Aldrich Chemical Company Inc., 1990BS
439.70.016Weast and Grasselli, 1989BS

Enthalpy of vaporization

ΔvapH (kcal/mol) Temperature (K) Method Reference Comment
15.7434.AStephenson and Malanowski, 1987Based on data from 419. to 580. K.; AC

Enthalpy of sublimation

ΔsubH (kcal/mol) Temperature (K) Method Reference Comment
23.8313.AStephenson and Malanowski, 1987Based on data from 298. to 343. K.; AC
24.81 ± 0.60315.N/AKratt, Beckhaus, et al., 1983Based on data from 293. to 338. K.; AC
20.7 ± 0.02309.TMEngelsman, 1955Based on data from 303. to 315. K.; AC
21.7 ± 0.2329.VWolf and Weghofer, 1938ALS

Enthalpy of fusion

ΔfusH (kcal/mol) Temperature (K) Method Reference Comment
6.5416398.N/AVan Miltenburg and Bouwstra, 1984DH
6.55398.2N/AAcree, 1991AC
6.62397.4ACBouwstra, Leeuw, et al., 1985AC

Entropy of fusion

ΔfusS (cal/mol*K) Temperature (K) Reference Comment
16.4398.Van Miltenburg and Bouwstra, 1984DH

Enthalpy of phase transition

ΔHtrs (kcal/mol) Temperature (K) Initial Phase Final Phase Reference Comment
6.6181397.40crystaline, IliquidBouwstra, De Leeuw, et al., 1985DH

Entropy of phase transition

ΔStrs (cal/mol*K) Temperature (K) Initial Phase Final Phase Reference Comment
16.6397.40crystaline, IliquidBouwstra, De Leeuw, et al., 1985DH

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 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

(E)-Stilbene + Hydrogen = Bibenzyl

By formula: C14H12 + H2 = C14H14

Quantity Value Units Method Reference Comment
Δr-18.59 ± 0.20kcal/molChydWilliams, 1942liquid phase; solvent: Acetic acid; Reanalyzed by Cox and Pilcher, 1970, Original value = -20.14 ± 0.36 kcal/mol; At 302 K

(E)-Stilbene = cis-Stilbene

By formula: C14H12 = C14H12

Quantity Value Units Method Reference Comment
Δr8.4 ± 5.6kcal/molCphaHerman and Goodman, 1989solid phase; solvent: Acetonitrile/water
Δr4.59 ± 0.09kcal/molCisoSaltiel, Ganapathy, et al., 1987gas phase; At 303.2-461.2 K

cis-Stilbene = (E)-Stilbene

By formula: C14H12 = C14H12

Quantity Value Units Method Reference Comment
Δr-1.2 ± 0.1kcal/molCmBastianelli, Caia, et al., 1991liquid phase; Thermal Isomerization
Δr-2.9 ± 0.3kcal/molCisoFischer, Muszkat, et al., 1968solid phase; solvent: Cyclohexane

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:
LL - Sharon G. Lias and Joel F. Liebman
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
B - John E. Bartmess

View reactions leading to C14H12+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
IE (evaluated)7.656 ± 0.001eVN/AN/AL

Electron affinity determinations

EA (eV) Method Reference Comment
0.390 ± 0.020LPESVogeler, Siegert, et al., 2011B
<0.390 ± 0.061ECDWojnarovits and Foldiak, 1981(E) isomer. EA is an upper limit: Chen and Wentworth, 1989. G3MP2B3 calculations indicate an EA of ca. 0.4 eV; B

Ionization energy determinations

IE (eV) Method Reference Comment
7.6558 ± 0.0005TETakahashi and Kimura, 1995LL
7.70 ± 0.02PEMaier and Turner, 1973LLK
7.70 ± 0.03PIPotapov, Kardash, et al., 1972LLK
7.76PEDewar and Goodman, 1972LLK
7.87PEKobayashi, Yokota, et al., 1975Vertical value; LLK
7.90 ± 0.05PEDistefano, Mazzucato, et al., 1975Vertical value; LLK
7.91 ± 0.05PEGoetz, Marschner, et al., 1974Vertical value; LLK

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

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


Mass spectrum (electron ionization)

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

Spectrum

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Mass spectrum
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Additional Data

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Owner NIST Mass Spectrometry Data Center
Collection (C) 2014 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin Japan AIST/NIMC Database- Spectrum MS-NW-4540
NIST MS number 228769

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


UV/Visible spectrum

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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: Victor Talrose, Eugeny B. Stern, Antonina A. Goncharova, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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UVVis spectrum
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Additional Data

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Source Rodebush and Feldman, 1946
Owner INEP CP RAS, NIST OSRD
Collection (C) 2007 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS
Source reference RAS UV No. 684
Instrument Beckman DU
Melting point 123
Boiling point 307; 166(12)

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, 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]

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]

Vogeler, Siegert, et al., 2011
Vogeler, F.; Siegert, S.; Marian, C.M.; Weinkauf, R., T-1, T-2 State Energies and Electron Affinities of Small alpha,omega-Diphenylpolyenes Investigated by Anion Photodetachment Photoelectron Spectroscopy and Excited-State Theory, Chemphyschem, 2011, 12, 10, 1948-1956, https://doi.org/10.1002/cphc.201001083 . [all data]

Wojnarovits and Foldiak, 1981
Wojnarovits, L.; Foldiak, G., Electron capture detection of aromatic hydrocarbons, J. Chromatogr. Sci., 1981, 206, 511. [all data]

Chen and Wentworth, 1989
Chen, E.C.M.; Wentworth, W.E., Experimental Determination of Electron Affinities of Organic Molecules, Mol. Cryst. Liq. Cryst., 1989, 171, 271. [all data]

Takahashi and Kimura, 1995
Takahashi, M.; Kimura, K., ZEKE Photoelectron spectra of trans-stilbene in the S1 state, J. Phys. Chem., 1995, 99, 1628. [all data]

Maier and Turner, 1973
Maier, J.P.; Turner, D.W., Steric inhibition of resonance studied by molecular photoelectron spectroscopy. Part 2. Phenylethylenes, J. Chem. Soc. Faraday Trans. 2, 1973, 69, 196. [all data]

Potapov, Kardash, et al., 1972
Potapov, V.K.; Kardash, I.E.; Sorokin, V.V.; Sokolov, S.A.; Evlasheva, T.I., Photoionization of heteroaromatic compounds, Khim. Vys. Energ., 1972, 6, 392. [all data]

Dewar and Goodman, 1972
Dewar, M.J.S.; Goodman, D.W., Photoelectron spectra of molecules. Part 5.--Polycyclic aromatic hydrocarbons, J. Chem. Soc. Faraday Trans. 2, 1972, 68, 1784. [all data]

Kobayashi, Yokota, et al., 1975
Kobayashi, T.; Yokota, K.; Nagakura, S., Photoelectron spectra of the cis- trans-isomers of some ethylene derivatives, Bull. Chem. Soc. Jpn., 1975, 48, 412. [all data]

Distefano, Mazzucato, et al., 1975
Distefano, G.; Mazzucato, U.; Modelli, A.; Pignataro, S.; Orlandi, G., Photoelectron (He I) spectroscopic study of styrylpyridines, J. Chem. Soc. Faraday Trans. 2, 1975, 71, 1583. [all data]

Goetz, Marschner, et al., 1974
Goetz, H.; Marschner, F.; Juds, H., Zur n-pi Wechselwirkung im Benzalanilin, Tetrahedron, 1974, 30, 1133. [all data]

Rodebush and Feldman, 1946
Rodebush, W.H.; Feldman, I., Ultraviolet absorption spectra of organic molecules. III. Mechanical interference of substituent groups with resonance configurations, J. Am. Chem. Soc., 1946, 68, 896-899. [all data]


Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, References