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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Reaction thermochemistry data
Go To: Top, Gas phase ion energetics data, Mass spectrum (electron ionization), 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° | -51.8 ± 2.9 | kJ/mol | Cm | Bonetskaya, Kravchenko, et al., 1985 | liquid phase; solvent: Diglyme; Trimerization |
| ΔrH° | 80.8 | kJ/mol | Cm | Bykova, Lebedev, et al., 1985 | liquid phase; Different experiment |
+
=
By formula: C7H5NO + C4H10O = C11H15NO2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -83.9 ± 4.4 | kJ/mol | Cm | Pannone and Macosko, 1987 | liquid phase |
| ΔrH° | -105. ± 1. | kJ/mol | Cm | Lovering and Laidler, 1962 | solid phase |
+
=
By formula: C7H5NO + C8H19N = C15H24N2O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -1088.8 ± 1.7 | kJ/mol | Cm | Kiselev, Malkov, et al., 1989 | liquid phase; solvent: Dioxane |
+
=
By formula: C7H5NO + C6H7N = C13H12N2O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -82.5 ± 2.0 | kJ/mol | Cm | Kiselev, Malkov, et al., 1989 | liquid phase; solvent: Dioxane |
=
+
By formula: C13H12N2O = C7H5NO + C6H7N
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 181.7 ± 4.2 | kJ/mol | Eqk | Chimishkyan, Svetlova, et al., 1984 | solid phase; Dissociation |
= 3
By formula: C21H15N3O3 = 3C7H5NO
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -80.8 | kJ/mol | Cm | Bykova, Lebedev, et al., 1985 | solid phase; Different experiment |
=
+
By formula: C9H12N2O = C7H5NO + C2H7N
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 134.2 ± 2.9 | kJ/mol | Eqk | Chimishkyan, Svetlova, et al., 1984 | solid phase |
+
=
By formula: C7H5NO + C6H7N = C13H12N2O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -89.1 ± 5.1 | kJ/mol | Cm | Pannone and Macosko, 1987 | liquid phase |
+
=
By formula: C7H5NO + C7H9N = C14H14N2O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -93.0 | kJ/mol | Cm | Pannone and Macosko, 1987 | liquid phase |
+
=
By formula: C7H5NO + C4H11N = C11H16NO2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -112. | kJ/mol | Cm | Pannone and Macosko, 1987 | liquid phase |
+
=
By formula: C7H5NO + C9H10O2 = C16H15NO3
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -196.7 | kJ/mol | Cm | Lebedev, Bykova, et al., 1988 | liquid phase |
Gas phase ion energetics data
Go To: Top, Reaction thermochemistry data, Mass spectrum (electron ionization), 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 |
Mass spectrum (electron ionization)
Go To: Top, Reaction 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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
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Additional Data
View image of digitized spectrum (can be printed in landscape orientation).
Due to licensing restrictions, this spectrum cannot be downloaded.
| Owner | NIST Mass Spectrometry Data Center Collection (C) 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
|---|---|
| Origin | NIST Mass Spectrometry Data Center, 1994 |
| NIST MS number | 134096 |
References
Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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]
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]
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]
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, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), References
- Symbols used in this document:
IE (evaluated) Recommended ionization energy ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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