(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+ Copy

  
• IUPAC Standard InChIKey: PJANXHGTPQOBST-VAWYXSNFSA-N Copy
• 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)-
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas phase thermochemistry data
  • Phase change data
  • Gas phase ion energetics data
  • IR Spectrum
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
  • Reaction thermochemistry data
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
  • NIST Polycyclic Aromatic Hydrocarbon Structure Index
• Options:
  • Switch to SI units

Data at NIST subscription sites:

• NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.

Gas phase thermochemistry data

Go To: Top, Phase change data, Gas phase ion energetics data, IR Spectrum, Gas Chromatography, 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

Phase change data

Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, IR Spectrum, Gas Chromatography, 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:
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

Reduced pressure boiling point

Enthalpy of vaporization

Enthalpy of sublimation

Enthalpy of fusion

Entropy of fusion

Enthalpy of phase transition

Entropy of phase transition

Gas phase ion energetics data

Go To: Top, Gas phase thermochemistry data, Phase change data, IR Spectrum, Gas Chromatography, References, Notes

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)

Electron affinity determinations

Ionization energy determinations

IR Spectrum

Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, Gas Chromatography, References, Notes

Data compiled by: Coblentz Society, Inc.

• SOLID (SPLIT MULL), FLUOROLUBE FOR 3800-1330 CM^-1, NUJOL FOR 1330-400 CM^-1 $$ SEE SPECTRUM NO. 4773 FOR "SOLUTION" RUN; BECKMAN IR-9 (GRATING); DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 2 cm^-1 resolution
• SOLUTION (10.5% IN CCl4 FOR 3800-1300, 2% IN CS2 FOR 1300-650, AND 10.5% CCl4 FPR 650-240 CM^-1) VERSUS SOLVENT; Not specified, most likely a grating or hybrid spectrometer.; DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm^-1 resolution
• SOLUTION (5% CCl4 FOR 3800-1350, 5% CS2 FOR 1350-400 CM^-1); DOW KBr FOREPRISM-GRATING; DIGITIZED BY COBLENTZ SOCIETY (BATCH I) FROM HARD COPY; 2 cm^-1 resolution

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

• gas; HP-GC/MS/IRD

Gas Chromatography

Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, 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: NIST Mass Spectrometry Data Center, William E. Wallace, director

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

View large format table.

Kovats' RI, polar column, isothermal

View large format table.

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

View large format table.

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

View large format table.

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

View large format table.

References

Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Gas Chromatography, 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]

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]

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]

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]

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]

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]

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

Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Gas Chromatography, References

• Symbols used in this document:
  

  EA	Electron affinity
  IE (evaluated)	Recommended ionization energy
  Tboil	Boiling point
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  ΔHtrs	Enthalpy of phase transition
  ΔStrs	Entropy of phase transition
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔfusH	Enthalpy of fusion
  ΔfusS	Entropy of fusion
  ΔsubH	Enthalpy of sublimation
  ΔsubH°	Enthalpy of sublimation at standard conditions
  ΔvapH	Enthalpy of vaporization
  ΔvapH°	Enthalpy of vaporization at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
• The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
• Customer support for NIST Standard Reference Data products.