1,3-Butadiene, 1,4-diphenyl-, (E,E)-
- Formula: C16H14
- Molecular weight: 206.2824
- IUPAC Standard InChI: InChI=1S/C16H14/c1-3-9-15(10-4-1)13-7-8-14-16-11-5-2-6-12-16/h1-14H/b13-7+,14-8+
- IUPAC Standard InChIKey: JFLKFZNIIQFQBS-FNCQTZNRSA-N
- CAS Registry Number: 538-81-8
- 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:
- Other names: trans,trans-1,4-Diphenyl-1,3-butadiene; (E,E)-(C6H5CH=CH)2; (E,E)-1,4-Diphenyl-1,3-butadiene; trans,trans-1,4-Diphenylbutadiene; Benzene, 1,1'-(1,3-butadiene-1,4-diyl)bis-, (E,E)-; 1,3-Butadiene, 1,4-diphenyl-, trans,trans-; 1,4-Diphenyl-trans-1,trans-3-butadiene; 1,4-Diphenyl-1,3-butadiene, trans,trans-; (E,E)-1,4-Diphenylbutadiene; all-trans-Diphenylbutadiene; [(1E,3E)-4-Phenyl-1,3-butadienyl]benzene; (1E,4E)-1,4-Diphenyl-1,3-butadiene; (E,E)-(c6H5Ch=ch2)2
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Condensed phase thermochemistry data
Go To: Top, Phase change data, Reaction thermochemistry data, 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
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔcH°solid | -2025.74 ± 0.48 | kcal/mol | Ccb | Coops, Hoijtink, et al., 1953 | Reanalyzed by Cox and Pilcher, 1970, Original value = -2026. ± 0.2 kcal/mol; Corresponding ΔfHºsolid = 42.717 kcal/mol (simple calculation by NIST; no Washburn corrections) |
| ΔcH°solid | -2022.7 ± 1.6 | kcal/mol | Ccb | Coates and Sutton, 1948 | Reanalyzed by Cox and Pilcher, 1970, Original value = -2023.0 ± 1.6 kcal/mol; Corresponding ΔfHºsolid = 39.68 kcal/mol (simple calculation by NIST; no Washburn corrections) |
| ΔcH°solid | -2029.90 ± 0.62 | kcal/mol | Ccb | Ott, 1928 | Corresponding ΔfHºsolid = 46.88 kcal/mol (simple calculation by NIST; no Washburn corrections) |
Phase change data
Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, 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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| Tboil | 623.2 | K | N/A | Aldrich Chemical Company Inc., 1990 | BS |
| Quantity | Value | Units | Method | Reference | Comment |
| Tfus | 421.4 | K | N/A | Berry, Lipsky, et al., 1956 | Uncertainty assigned by TRC = 0.7 K; TRC |
| Tfus | 423.7 | K | N/A | Dombrovsky and Terent'ev, 1956 | Uncertainty assigned by TRC = 2. K; TRC |
| Tfus | 425.9 | K | N/A | Cram and Steinberg, 1951 | Uncertainty assigned by TRC = 4. K; TRC |
| Tfus | 426.4 | K | N/A | Hofer and Peebles, 1951 | Uncertainty assigned by TRC = 2. K; TRC |
Enthalpy of sublimation
| ΔsubH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 39.7 ± 1.6 | 293. | V | Coates and Sutton, 1948 | Reanalyzed by Cox and Pilcher, 1970, Original value = 22.3 ± 0.5 kcal/mol; ALS |
Reaction thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, 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
2 +
=
By formula: 2H2 + C16H14 = C16H18
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -44.04 ± 0.15 | kcal/mol | Chyd | Williams, 1942 | liquid phase; solvent: Acetic acid; At 302 K |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Coops, Hoijtink, et al., 1953
Coops, J.; Hoijtink, G.J.; Kramer, Th.J.E.; Faber, A.C.,
Thermochemical investigations on arylethenes. II. Heats of combustion of some para and orthotolylethenes and phenylbutadienes,
Rec. Trav. Chim. Pays/Bas, 1953, 72, 765. [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]
Coates and Sutton, 1948
Coates, G.E.; Sutton, L.E.,
The heats of formation of the -N=N- and >C=N- bonds,
J. Chem. Soc., 1948, 1187-1196. [all data]
Ott, 1928
Ott, E.,
Nachtrage zu der Untersuchung uber die Habhydrierung der Acetylen-Binding und die Abhangigkeit der Konfiguration der entstehenden Athylen-Verbin-dungen von der Reaktionsgeschwindigkeit,
Ber., 1928, 61, 2119-2123. [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]
Berry, Lipsky, et al., 1956
Berry, P.J.; Lipsky, S.; Burton, M.,
Radiation-Induced Luminescence Part 2 - The Effect of Oxygen and Bromobenzene,
Trans. Faraday Soc., 1956, 52, 311. [all data]
Dombrovsky and Terent'ev, 1956
Dombrovsky, A.V.; Terent'ev, A.P.,
Haloarylation of Undaturated Compounds with Aromatic Diazo Compounds I. Reaction of Phenyldiazonium Chloride and Bromidw with 1,3-Butadiene and Some Transformations of 4-Chloro-1-phenyl-2-butene,
Zh. Obshch. Khim., 1956, 26, 2776-82. [all data]
Cram and Steinberg, 1951
Cram, D.J.; Steinberg, H.,
J. Am. Chem. Soc., 1951, 73, 5691. [all data]
Hofer and Peebles, 1951
Hofer, L.J.; Peebles, W.C.,
X-Ray Diffraction Patterns of Solid Aromatic Hydrocarbons,
Anal. Chem., 1951, 23, 690. [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]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, References
- Symbols used in this document:
Tboil Boiling point Tfus Fusion (melting) point ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔsubH Enthalpy of sublimation - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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