Benzene, isocyanato-
- Formula: C7H5NO
- Molecular weight: 119.1207
- IUPAC Standard InChI: InChI=1S/C7H5NO/c9-6-8-7-4-2-1-3-5-7/h1-5H
- IUPAC Standard InChIKey: DGTNSSLYPYDJGL-UHFFFAOYSA-N
- CAS Registry Number: 103-71-9
- 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. - Other names: Isocyanic acid, phenyl ester; Carbanil; Isocyanatobenzene; Mondur P; Phenyl carbonimide; Phenyl isocyanate; Phenylcarbimide; Fenylisokyanat; Karbanil; UN 2487; Phenyl ester of isocyanic acid; Additive TI; NSC 74454
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Gas phase thermochemistry 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | -3.48 ± 0.27 | kcal/mol | Ccr | Steele, Chirico, et al., 1996 | |
| ΔfH°gas | -5.28 | kcal/mol | Cm | Korovin and Margolin, 1976 |
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°liquid | -14.60 ± 0.27 | kcal/mol | Ccr | Steele, Chirico, et al., 1996 | ALS |
| ΔfH°liquid | -8.10 ± 0.31 | kcal/mol | Cm | Bykova, Lebedev, et al., 1985 | Different experiment; ALS |
| ΔfH°liquid | -8.10 ± 0.31 | kcal/mol | Ccb | Lebedev, Rabinovich, et al., 1977 | Different experiment; ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -814.55 ± 0.20 | kcal/mol | Ccr | Steele, Chirico, et al., 1996 | ALS |
| ΔcH°liquid | -825.79 ± 0.31 | kcal/mol | Ccb | Lebedev, Rabinovich, et al., 1977 | Different experiment; ALS |
| ΔcH°liquid | -813.2 | kcal/mol | Ccb | Strepikheev, Baranov, et al., 1962 | ALS |
Constant pressure heat capacity of liquid
| Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 44.50 | 298.15 | Steele, Chirico, et al., 1993 | 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
3 =
By formula: 3C7H5NO = C21H15N3O3
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -12.4 ± 0.69 | kcal/mol | Cm | Bonetskaya, Kravchenko, et al., 1985 | liquid phase; solvent: Diglyme; Trimerization |
| ΔrH° | 19.3 | kcal/mol | Cm | Bykova, Lebedev, et al., 1985 | liquid phase; Different experiment |
+
=
By formula: C7H5NO + C4H10O = C11H15NO2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -20.1 ± 1.1 | kcal/mol | Cm | Pannone and Macosko, 1987 | liquid phase |
| ΔrH° | -25.1 ± 0.3 | kcal/mol | Cm | Lovering and Laidler, 1962 | solid phase |
+
=
By formula: C7H5NO + C8H19N = C15H24N2O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -260.23 ± 0.41 | kcal/mol | Cm | Kiselev, Malkov, et al., 1989 | liquid phase; solvent: Dioxane |
+
=
By formula: C7H5NO + C6H7N = C13H12N2O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -19.7 ± 0.48 | kcal/mol | Cm | Kiselev, Malkov, et al., 1989 | liquid phase; solvent: Dioxane |
=
+
By formula: C13H12N2O = C7H5NO + C6H7N
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 43.4 ± 1.0 | kcal/mol | Eqk | Chimishkyan, Svetlova, et al., 1984 | solid phase; Dissociation |
= 3
By formula: C21H15N3O3 = 3C7H5NO
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -19.3 | kcal/mol | Cm | Bykova, Lebedev, et al., 1985 | solid phase; Different experiment |
=
+
By formula: C9H12N2O = C7H5NO + C2H7N
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 32.07 ± 0.69 | kcal/mol | Eqk | Chimishkyan, Svetlova, et al., 1984 | solid phase |
+
=
By formula: C7H5NO + C6H7N = C13H12N2O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -21.3 ± 1.2 | kcal/mol | Cm | Pannone and Macosko, 1987 | liquid phase |
+
=
By formula: C7H5NO + C7H9N = C14H14N2O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -22.2 | kcal/mol | Cm | Pannone and Macosko, 1987 | liquid phase |
+
=
By formula: C7H5NO + C4H11N = C11H16NO2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -26.8 | kcal/mol | Cm | Pannone and Macosko, 1987 | liquid phase |
+
=
By formula: C7H5NO + C9H10O2 = C16H15NO3
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -47.01 | kcal/mol | Cm | Lebedev, Bykova, et al., 1988 | liquid 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.; Tasker, I.R.,
Thermodynamic properties and ideal-gas enthalpies of formation for cyclohexene, phthalan (2,5-dihydrobenzo-3,4-furan), isoxazole, octylamine, dioctylamine, trioctylamine, phenyl isocyanate, and 1,4,5,6-tetrahydropyrimidine,
J. Chem. Eng. Data, 1996, 41, 1269-1284. [all data]
Korovin and Margolin, 1976
Korovin, A.I.; Margolin, L.N.,
Thermodynamic functions of phenyl isocyanate,
Zh. Fiz. Khim., 1976, 50, 2923-29. [all data]
Bykova, Lebedev, et al., 1985
Bykova, T.A.; Lebedev, B.V.; Kiparisova, E.G.; Tarasov, E.N.; Frenkel, Ts.M.; Pankratov, V.A.; Vinogradova, S.V.; Korshank, V.V.,
Thermodynamics of phenyl isocyanate, the process of its cyclotrimerization, and the triphenyl isocyanurate that is formed, in the 0-330°K interval,
J. Gen. Chem. USSR, 1985, 55, 2303-2308. [all data]
Lebedev, Rabinovich, et al., 1977
Lebedev, B.V.; Rabinovich, I.B.; Kiparisova, E.G.; Evstropov, A.A.; Korshak, V.V.; Pankratov, V.A.; Larina, L.F.,
Thermodynamics of the polycyclotrimerization of aromatic dicyanates and diisocyanates,
Dokl. Phys. Chem. (Engl. Transl.), 1977, 237, 1081-1084, In original 383. [all data]
Strepikheev, Baranov, et al., 1962
Strepikheev, Yu.A.; Baranov, Yu.I.; Burmistrova, O.A.,
Determination of the heats of combustion and the heat capacities of several mono- and di-isocyanates,
Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol., 1962, 5, 387-390. [all data]
Steele, Chirico, et al., 1993
Steele, W.V.; Chirico, R.D.; Knipmeyer, S.E.; Nguyen, A.; Tasker, I.R.,
Determination of ideal gas enthalpies of formation for key compounds the 1991 project results,
DIPPR Project, 1993, 871, NIPER-716. [all data]
Bonetskaya, Kravchenko, et al., 1985
Bonetskaya, A.K.; Kravchenko, M.A.; Frenkel, Ts.M.; Pankratov, V.A.; Vinogradova, S.V.; Korshak, V.V.,
Kinetics and heat of cyclotrimerization of aryl and alkyl isocyanates,
Vysokomol. Soedin., Ser. A, 1985, 27, 1269-1273. [all data]
Pannone and Macosko, 1987
Pannone, M.C.; Macosko, C.W.,
Kinetics of isocyanate amine reactions,
J. Appl. Polym. Sci., 1987, 34, 2409-2432. [all data]
Lovering and Laidler, 1962
Lovering, E.G.; Laidler, K.J.,
Thermochemical studies of some alcohol-isocyanate reactions,
Can. J. Chem., 1962, 40, 26-30. [all data]
Kiselev, Malkov, et al., 1989
Kiselev, V.D.; Malkov, V.B.; Murzin, D.G.; Shakirov, I.M.; Konovalov, A.I.,
Thermochemical study of the reaction of isocyanate with amines,
Dokl. Phys. Chem. (Engl. Transl.), 1989, 308, 711-713, In original 111. [all data]
Chimishkyan, Svetlova, et al., 1984
Chimishkyan, A.L.; Svetlova, L.P.; Leonova, T.V.; Gluyaev, N.D.,
Thermal decomposition of substituted ureas,
J. Gen. Chem. USSR, 1984, 54, 1317-1320. [all data]
Lebedev, Bykova, et al., 1988
Lebedev, B.V.; Bykova, T.A.; Kiparisova, E.G.; Frenkel, Ts.M.; Fainleib, A.M.; Pankratov, V.A.,
Thermodynamics of phenyl glycidyl ether and its reactions with diphenylcarbodiimide and phenyl isocyanate with the formation of iminooxazolidine and oxazolidinone in the 0-330 K range,
Bull. Acad. Sci. USSR, Div. Chem. Sci., 1988, 1082-10. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, References
- Symbols used in this document:
Cp,liquid Constant pressure heat capacity of liquid ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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