Azobenzene, (E)-
- Formula: C12H10N2
- Molecular weight: 182.2212
- IUPAC Standard InChI: InChI=1S/C12H10N2/c1-3-7-11(8-4-1)13-14-12-9-5-2-6-10-12/h1-10H
- IUPAC Standard InChIKey: DMLAVOWQYNRWNQ-UHFFFAOYSA-N
- CAS Registry Number: 17082-12-1
- 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. - Species with the same structure:
- Other names: Diazene, diphenyl-, (E)-; trans-Azobenzene; (E)-Diphenyldiazene; Diazene,diphenyl-,(trans)-
- Information on this page:
- Other data available:
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Gas phase thermochemistry 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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | 96.92 ± 0.31 | kcal/mol | Ccr | Steele, Chirico, et al., 1996 | Hfusion=21.3±0.5 kJ/mol; ALS |
| ΔfH°gas | 96.13 ± 0.65 | kcal/mol | Ccb | Dias, Minas Da Piedade, et al., 1992 | ALS |
| ΔfH°gas | 96.51 | kcal/mol | N/A | Schulze, Petrick, et al., 1977 | Value computed using ΔfHsolid° value of 310.2±3.4 kj/mol from Schulze, Petrick, et al., 1977 and ΔsubH° value of 93.6 kj/mol from Steele, Chirico, et al., 1996.; DRB |
| ΔfH°gas | 98.85 | kcal/mol | N/A | Cole and Gilbert, 1951 | Value computed using ΔfHsolid° value of 320.0 kj/mol from Cole and Gilbert, 1951 and ΔsubH° value of 93.6 kj/mol from Steele, Chirico, et al., 1996.; DRB |
| ΔfH°gas | 98.14 | kcal/mol | N/A | Corruccini and Gilbert, 1939 | Value computed using ΔfHsolid° value of 317.0±2.0 kj/mol from Corruccini and Gilbert, 1939 and ΔsubH° value of 93.6 kj/mol from Steele, Chirico, et al., 1996.; DRB |
Condensed phase thermochemistry data
Go To: Top, Gas 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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°solid | 74.429 | kcal/mol | Ccr | Steele, Chirico, et al., 1996 | Hfusion=21.3±0.5 kJ/mol; ALS |
| ΔfH°solid | 73.76 ± 0.45 | kcal/mol | Ccb | Dias, Minas Da Piedade, et al., 1992 | ALS |
| ΔfH°solid | 74.14 ± 0.81 | kcal/mol | Ccb | Schulze, Petrick, et al., 1977 | Reanalyzed by Pedley, Naylor, et al., 1986, Original value = 74.40 ± 0.81 kcal/mol; Hfusion=22.6±0.1 kJ/mol; ALS |
| ΔfH°solid | 76.49 | kcal/mol | Ccb | Cole and Gilbert, 1951 | ALS |
| ΔfH°solid | 75.7 ± 0.4 | kcal/mol | Ccb | Corruccini and Gilbert, 1939 | ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°solid | -1544.62 ± 0.21 | kcal/mol | Ccr | Steele, Chirico, et al., 1996 | Hfusion=21.3±0.5 kJ/mol; ALS |
| ΔcH°solid | -1544.0 ± 0.24 | kcal/mol | Ccb | Dias, Minas Da Piedade, et al., 1992 | ALS |
| ΔcH°solid | -1544.3 ± 0.81 | kcal/mol | Ccb | Schulze, Petrick, et al., 1977 | Hfusion=22.6±0.1 kJ/mol; ALS |
| ΔcH°solid | -1546.7 | kcal/mol | Ccb | Cole and Gilbert, 1951 | ALS |
| ΔcH°solid | -1545.6 | kcal/mol | Ccb | Corruccini and Gilbert, 1939 | ALS |
Constant pressure heat capacity of solid
| Cp,solid (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 54.7 | 298.15 | Schulze, Petrick, et al., 1977 | T = 298 to 333 K. Cp(c) = 229 + 1.086(T - 298.15 K) J/mol*K (298 to 333 K).; DH |
Reaction thermochemistry data
Go To: Top, Gas phase thermochemistry data, Condensed phase 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
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
C12H10N2 =
By formula: C12H10N2 = C12H10N2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -10.8 ± 0.57 | kcal/mol | Cpha | Dias, Minas Da Piedade, et al., 1992 | solid phase; Photoisomerization |
| ΔrH° | -11.5 ± 0.07 | kcal/mol | Ciso | Wolf and Cammenga, 1977 | solid phase |
| ΔrH° | -11.3 | kcal/mol | Ciso | Wolf and Cammenga, 1977 | gas phase; Gas phase |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry 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.
Steele, Chirico, et al., 1996
Steele, W.V.; Chirico, R.D.; Knipmeyer, S.E.; Nguyen, A.; Smith, N.K.,
Thermodynamic properties and ideal-gas enthalpies of formation for butyl vinyl ether, 1,2-dimethoxyethane, methyl glycolate, bicyclo[2.2.1]hept-2-ene, 5-vinylbicyclo[2.2.1]hept-2-ene, trans-azobenzene, butyl acrylate, di-tert-butyl ether, and hexane-1,6-diol,
J. Chem. Eng. Data, 1996, 41, 1285-1302. [all data]
Dias, Minas Da Piedade, et al., 1992
Dias, A.R.; Minas Da Piedade, M.E.; Martinho Simoes, J.A.; Simoni, J.A.; Teixeira, C.; Diogo, H.P.; Meng-Yen, Y.; Pilcher, G.,
Enthalpies of formation of cis-azobenzene and trans-azobenzene,
J. Chem. Thermodyn., 1992, 24, 439-447. [all data]
Schulze, Petrick, et al., 1977
Schulze, F.W.; Petrick, H.J.; Cammenga, H.K.,
Thermodynamic properties of structural analogues benzo[c]cinnoline, trans-azobenzene, and cis-azobenzene,
Z. Phys. Chem. (Neue Folge), 1977, 107, 1-19. [all data]
Cole and Gilbert, 1951
Cole, L.G.; Gilbert, E.C.,
The heats of combustion of some nitrogen compounds and the apparent energy of the N-N bond,
J. Am. Chem. Soc., 1951, 73, 5423-5427. [all data]
Corruccini and Gilbert, 1939
Corruccini, R.J.; Gilbert, E.C.,
The heat of combustion of cis- and trans-azobenzene,
J. Am. Chem. Soc., 1939, 61, 2925-2927. [all data]
Pedley, Naylor, et al., 1986
Pedley, J.B.; Naylor, R.D.; Kirby, S.P.,
Thermochemical Data of Organic Compounds, Chapman and Hall, New York, 1986, 1-792. [all data]
Wolf and Cammenga, 1977
Wolf, E.; Cammenga, H.K.,
Thermodynamic and kinetic investigation of the thermal isomerization of cis-azobenzene,
Z. Phys. Chem. (Neue Folge), 1977, 107, 21-38. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, References
- Symbols used in this document:
Cp,solid Constant pressure heat capacity of solid ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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