(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+
- IUPAC Standard InChIKey: PJANXHGTPQOBST-VAWYXSNFSA-N
- 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:
- 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)-
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Gas phase thermochemistry data
Go To: Top, 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 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 |
|---|---|---|---|---|---|
| ΔfH°gas | 52.49 | kcal/mol | N/A | Lobanov and Karmanova, 1971 | Value 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 |
| ΔfH°gas | 53.36 | kcal/mol | Ccb | Marantz and Armstrong, 1968 | see Marantz and Armstrong, 1968, 2; ALS |
| ΔfH°gas | 53.63 | kcal/mol | N/A | Richardson and Parks, 1939 | Value 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 |
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 ± 0.001 | eV | N/A | N/A | L |
Electron affinity determinations
| EA (eV) | Method | Reference | Comment |
|---|---|---|---|
| 0.390 ± 0.020 | LPES | Vogeler, Siegert, et al., 2011 | B |
| <0.390 ± 0.061 | ECD | Wojnarovits 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 ± 0.0005 | TE | Takahashi and Kimura, 1995 | LL |
| 7.70 ± 0.02 | PE | Maier and Turner, 1973 | LLK |
| 7.70 ± 0.03 | PI | Potapov, Kardash, et al., 1972 | LLK |
| 7.76 | PE | Dewar and Goodman, 1972 | LLK |
| 7.87 | PE | Kobayashi, Yokota, et al., 1975 | Vertical value; LLK |
| 7.90 ± 0.05 | PE | Distefano, Mazzucato, et al., 1975 | Vertical value; LLK |
| 7.91 ± 0.05 | PE | Goetz, Marschner, et al., 1974 | Vertical value; LLK |
IR Spectrum
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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
References
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, IR 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]
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]
Notes
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, IR 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 - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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