(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
  View 3d structure (requires JavaScript / HTML 5)
• 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
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
  • Phase change data
  • Gas Chromatography
• 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, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible 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 as indicated in comments:
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Reaction thermochemistry data

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

 +  =

By formula: C₁₄H₁₂ + H₂ = C₁₄H₁₄

=

By formula: C₁₄H₁₂ = C₁₄H₁₂

=

By formula: C₁₄H₁₂ = C₁₄H₁₂

Gas phase ion energetics data

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

Mass spectrum (electron ionization)

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, UV/Visible 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

Spectrum

Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.

For Zoom

1.) Enter the desired X axis range (e.g., 100, 200)

2.) Check here for automatic Y scaling

3.) Press here to zoom

Additional Data

UV/Visible spectrum

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), 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: Victor Talrose, Eugeny B. Stern, Antonina A. Goncharova, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.

For Zoom

1.) Enter the desired X axis range (e.g., 100, 200)

2.) Check here for automatic Y scaling

3.) Press here to zoom

Additional Data

References

Go To: Top, Gas phase thermochemistry 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]

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]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [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, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, References

• Symbols used in this document:
  

  EA	Electron affinity
  IE (evaluated)	Recommended ionization energy
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔrH°	Enthalpy of reaction 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.