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cis-Stilbene

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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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Deltacliquid-7404.05 ± 0.75kJ/molCcbYates and McDonald, 1971Corresponding «DELTA»fliquid = 179.9 kJ/mol (simple calculation by NIST; no Washburn corrections)
Deltacliquid-7407.6 ± 1.5kJ/molCcbCoops and Hoijtink, 1950Reanalyzed by Cox and Pilcher, 1970, Original value = -7404.1 ± 0.74 kJ/mol; Corresponding «DELTA»fliquid = 183.48 kJ/mol (simple calculation by NIST; no Washburn corrections)

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:
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

Quantity Value Units Method Reference Comment
Deltavap70.5 ± 0.4kJ/molGSCammenga, Emel'yanenko, et al., 2009Based on data from 308. - 343. K.; AC
Deltavap50.3 ± 1.0kJ/molN/ABrackman and Plesch, 1952Based on data from 276. - 286. K. See also Cammenga, Emel'yanenko, et al., 2009.; AC
Deltavap66. ± 1.kJ/molVBrackman and Plesch, 1952, 2ALS

Reduced pressure boiling point

Tboil (K) Pressure (bar) Reference Comment
356.20.0005Aldrich Chemical Company Inc., 1990BS

Enthalpy of vaporization

DeltavapH (kJ/mol) Temperature (K) Method Reference Comment
66.5388.AStephenson and Malanowski, 1987Based on data from 373. - 428. K.; AC

Enthalpy of sublimation

DeltasubH (kJ/mol) Temperature (K) Method Reference Comment
90.8 ± 0.8329.VWolf and Weghofer, 1938ALS

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

Hydrogen + cis-Stilbene = Bibenzyl

By formula: H2 + C14H12 = C14H14

Quantity Value Units Method Reference Comment
Deltar-131.5 ± 0.84kJ/molChydWilliams, 1942liquid phase; solvent: Acetic acid; Reanalyzed by Cox and Pilcher, 1970, Original value = -108.0 ± 8.5 kJ/mol; At 302 K

(E)-Stilbene = cis-Stilbene

By formula: C14H12 = C14H12

Quantity Value Units Method Reference Comment
Deltar35. ± 23.kJ/molCphaHerman and Goodman, 1989solid phase; solvent: Acetonitrile/water
Deltar19.2 ± 0.4kJ/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
Deltar-5.0 ± 0.4kJ/molCmBastianelli, Caia, et al., 1991liquid phase; Thermal Isomerization
Deltar-12. ± 1.kJ/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 compiled by: Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

View reactions leading to C14H12+ (ion structure unspecified)

Ionization energy determinations

IE (eV) Method Reference Comment
7.80 ± 0.02PEMaier and Turner, 1973 
8.17PEKobayashi, Yokota, et al., 1975Vertical value

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 NIST Mass Spectrometry Data Center, 1998.
NIST MS number 291438

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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, Alexander N. Yermakov, Alexy A. Usov, Antonina A. Goncharova, Axlexander N. Leskin, 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 Lang (editor), 1967
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. 19154
Instrument Cary II M
Boiling point 159/ 45 mm

References

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, 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.

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]

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]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]

Cammenga, Emel'yanenko, et al., 2009
Cammenga, Heiko K.; Emel'yanenko, Vladimir N.; Verevkin, Sergey P., Re-investigation and Data Assessment of the Isomerization and 2,2´-Cyclization of Stilbenes and Azobenzenes «8224», Ind. Eng. Chem. Res., 2009, 48, 22, 10120-10128, https://doi.org/10.1021/ie900800q . [all data]

Brackman and Plesch, 1952
Brackman, D.S.; Plesch, P.H., 406. Some physical properties of cis-stilbene, J. Chem. Soc., 1952, 2188, https://doi.org/10.1039/jr9520002188 . [all data]

Brackman and Plesch, 1952, 2
Brackman, D.S.; Plesch, P.H., Some physical properties of cis-stilbene, J. Chem. Soc., 1952, 2188-21. [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]

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]

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

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]

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]

Lang (editor), 1967
Lang (editor), L., Absorption Spectra in the Ultraviolet and Visible Region, 1967, 9, 111. [all data]


Notes

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