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, Gas phase ion energetics 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 | -14.5 ± 1.2 | kJ/mol | Ccr | Steele, Chirico, et al., 1996 | |
| ΔfH°gas | -22.1 | kJ/mol | Cm | Korovin and Margolin, 1976 |
Condensed phase thermochemistry data
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics 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 | -61.1 ± 1.1 | kJ/mol | Ccr | Steele, Chirico, et al., 1996 | ALS |
| ΔfH°liquid | -33.9 ± 1.3 | kJ/mol | Cm | Bykova, Lebedev, et al., 1985 | Different experiment; ALS |
| ΔfH°liquid | -33.9 ± 1.3 | kJ/mol | Ccb | Lebedev, Rabinovich, et al., 1977 | Different experiment; ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -3408.07 ± 0.85 | kJ/mol | Ccr | Steele, Chirico, et al., 1996 | ALS |
| ΔcH°liquid | -3455.1 ± 1.3 | kJ/mol | Ccb | Lebedev, Rabinovich, et al., 1977 | Different experiment; ALS |
| ΔcH°liquid | -3402. | kJ/mol | Ccb | Strepikheev, Baranov, et al., 1962 | ALS |
Constant pressure heat capacity of liquid
| Cp,liquid (J/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 186.2 | 298.15 | Steele, Chirico, et al., 1993 | DH |
Gas phase ion energetics 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 evaluated as indicated in comments:
L - Sharon G. Lias
Data compiled as indicated in comments:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
View reactions leading to C7H5NO+ (ion structure unspecified)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| IE (evaluated) | 8.77 ± 0.02 | eV | N/A | N/A | L |
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 8.8 | PE | Kobayashi and Nagakura, 1975 | LLK |
| 9.2 | EI | Compernolle and DeSchryver, 1975 | LLK |
| 8.77 ± 0.02 | PI | Watanabe, Nakayama, et al., 1962 | RDSH |
| 9.00 | PE | Kobayashi and Nagakura, 1975 | Vertical value; LLK |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Gas phase ion energetics 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]
Kobayashi and Nagakura, 1975
Kobayashi, T.; Nagakura, S.,
Photoelectron spectra of phenyl isocyanates and phenyl isothio- cyanate,
J. Electron Spectrosc. Relat. Phenom., 1975, 7, 488. [all data]
Compernolle and DeSchryver, 1975
Compernolle, F.; DeSchryver, F.,
Nonconcerted cycloreversion by electron impact of substituted 2,4-azetidinediones. Relations between the mass spectral and photochemical reactions,
J. Am. Chem. Soc., 1975, 97, 3909. [all data]
Watanabe, Nakayama, et al., 1962
Watanabe, K.; Nakayama, T.; Mottl, J.,
Ionization potentials of some molecules,
J. Quant. Spectry. Radiative Transfer, 1962, 2, 369. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
Cp,liquid Constant pressure heat capacity of liquid IE (evaluated) Recommended ionization energy 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 - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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