cis-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-QXMHVHEDSA-N Copy
• CAS Registry Number: 645-49-8
• 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:
  • (E)-Stilbene
  • Stilbene
• Other names: (Z)-Stilbene; Benzene, 1,1'-(1,2-ethenediyl)bis-, (Z)-; Stilbene, (Z)-; cis-1,2-Diphenylethylene; Isostilbene; (Z)-1,2-Diphenylethene; Benzene, 1,1'-(1,2-ethenedyl)bis-, (Z)-; Dibenzal (cis); 1,2-Diphenylethene, (Z)-; (1,2-Ethenediyl)-1,1'-bisbenzene, (Z)-; 1,cis-2-Diphenylethene; 1,cis-2-Diphenylethylene; cis-Diphenylethene; (Z)-1,2-Diphenylethylene; cis-1,2-Diphenylethene; 1,1'-(1,2-Ethanediyl)bis[benzene], cis; Benzene, 1,1'-(1Z)-1,2-ethenediylbis-
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Phase change data
  • Gas phase ion energetics data
  • 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
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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

Reduced pressure boiling point

Enthalpy of vaporization

Enthalpy of sublimation

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

Gas Chromatography

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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

Kovats' RI, non-polar column, isothermal

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Kovats' RI, polar column, isothermal

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References

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

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]

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]

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]

Notes

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• Symbols used in this document:
  

  Tboil	Boiling point
  ΔsubH	Enthalpy of sublimation
  ΔvapH	Enthalpy of vaporization
  ΔvapH°	Enthalpy of vaporization at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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