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

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Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_gas	-14.5 ± 1.2	kJ/mol	Ccr	Steele, Chirico, et al., 1996
Δ_fH°_gas	-22.1	kJ/mol	Cm	Korovin and Margolin, 1976

Condensed phase thermochemistry data

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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
Δ_fH°_liquid	-61.1 ± 1.1	kJ/mol	Ccr	Steele, Chirico, et al., 1996	ALS
Δ_fH°_liquid	-33.9 ± 1.3	kJ/mol	Cm	Bykova, Lebedev, et al., 1985	Different experiment; ALS
Δ_fH°_liquid	-33.9 ± 1.3	kJ/mol	Ccb	Lebedev, Rabinovich, et al., 1977	Different experiment; ALS
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_liquid	-3408.07 ± 0.85	kJ/mol	Ccr	Steele, Chirico, et al., 1996	ALS
Δ_cH°_liquid	-3455.1 ± 1.3	kJ/mol	Ccb	Lebedev, Rabinovich, et al., 1977	Different experiment; ALS
Δ_cH°_liquid	-3402.	kJ/mol	Ccb	Strepikheev, Baranov, et al., 1962	ALS

Constant pressure heat capacity of liquid

C_p,liquid (J/mol*K)	Temperature (K)	Reference	Comment
186.2	298.15	Steele, Chirico, et al., 1993	DH

Phase change data

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Data compiled as indicated in comments:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos

Quantity	Value	Units	Method	Reference	Comment
T_c	675.	K	N/A	Steele, Chirico, et al., 1996, 2	Uncertainty assigned by TRC = 3. K; fitting parameter in Wagner equation for vapor pressure; TRC
Quantity	Value	Units	Method	Reference	Comment
P_c	45.40	bar	N/A	Steele, Chirico, et al., 1996, 2	Uncertainty assigned by TRC = 3.00 bar; from extrapolation of obs. vapor pressure to Tc; TRC
Quantity	Value	Units	Method	Reference	Comment
ρ_c	2.928	mol/l	N/A	Steele, Chirico, et al., 1996, 2	Uncertainty assigned by TRC = 0.17 mol/l; TRC
Quantity	Value	Units	Method	Reference	Comment
Δ_vapH°	46.5 ± 0.3	kJ/mol	V	Steele, Chirico, et al., 1996	ALS
Δ_vapH°	46.5 ± 0.3	kJ/mol	EB	Steele, Chirico, et al., 1996	Based on data from 329. to 445. K.; AC
Δ_vapH°	45.0	kJ/mol	A	Stephenson and Malanowski, 1987	Based on data from 283. to 439. K. See also Stull, 1947.; AC

Antoine Equation Parameters

log₁₀(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)

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Temperature (K)	A	B	C	Reference	Comment
283.8 to 438.8	4.52289	1800.757	-40.303	Stull, 1947	Coefficents calculated by NIST from author's data.

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:

Reaction thermochemistry data

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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 Benzene, isocyanato- =

By formula: 3C₇H₅NO = C₂₁H₁₅N₃O₃

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-51.8 ± 2.9	kJ/mol	Cm	Bonetskaya, Kravchenko, et al., 1985	liquid phase; solvent: Diglyme; Trimerization
Δ_rH°	80.8	kJ/mol	Cm	Bykova, Lebedev, et al., 1985	liquid phase; Different experiment

Benzene, isocyanato- + =

By formula: C₇H₅NO + C₄H₁₀O = C₁₁H₁₅NO₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-83.9 ± 4.4	kJ/mol	Cm	Pannone and Macosko, 1987	liquid phase
Δ_rH°	-105. ± 1.	kJ/mol	Cm	Lovering and Laidler, 1962	solid phase

Benzene, isocyanato- + =

By formula: C₇H₅NO + C₈H₁₉N = C₁₅H₂₄N₂O

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-1088.8 ± 1.7	kJ/mol	Cm	Kiselev, Malkov, et al., 1989	liquid phase; solvent: Dioxane

Benzene, isocyanato- + =

By formula: C₇H₅NO + C₆H₇N = C₁₃H₁₂N₂O

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-82.5 ± 2.0	kJ/mol	Cm	Kiselev, Malkov, et al., 1989	liquid phase; solvent: Dioxane

= Benzene, isocyanato- +

By formula: C₁₃H₁₂N₂O = C₇H₅NO + C₆H₇N

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	181.7 ± 4.2	kJ/mol	Eqk	Chimishkyan, Svetlova, et al., 1984	solid phase; Dissociation

= 3 Benzene, isocyanato-

By formula: C₂₁H₁₅N₃O₃ = 3C₇H₅NO

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-80.8	kJ/mol	Cm	Bykova, Lebedev, et al., 1985	solid phase; Different experiment

= Benzene, isocyanato- +

By formula: C₉H₁₂N₂O = C₇H₅NO + C₂H₇N

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	134.2 ± 2.9	kJ/mol	Eqk	Chimishkyan, Svetlova, et al., 1984	solid phase

Benzene, isocyanato- + =

By formula: C₇H₅NO + C₆H₇N = C₁₃H₁₂N₂O

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-89.1 ± 5.1	kJ/mol	Cm	Pannone and Macosko, 1987	liquid phase

Benzene, isocyanato- + =

By formula: C₇H₅NO + C₇H₉N = C₁₄H₁₄N₂O

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-93.0	kJ/mol	Cm	Pannone and Macosko, 1987	liquid phase

Benzene, isocyanato- + =

By formula: C₇H₅NO + C₄H₁₁N = C₁₁H₁₆NO₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-112.	kJ/mol	Cm	Pannone and Macosko, 1987	liquid phase

Benzene, isocyanato- + =

By formula: C₇H₅NO + C₉H₁₀O₂ = C₁₆H₁₅NO₃

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-196.7	kJ/mol	Cm	Lebedev, Bykova, et al., 1988	liquid phase

Gas phase ion energetics data

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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, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Notes

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]

Steele, Chirico, et al., 1996, 2
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 Dioctylamine, trioctylamine, Phenyl Isocyanate, and 1,4,5,6-Tetrahydropyrimidine, J. Chem. Eng. Data, 1996, 41, 1269-84. [all data]

Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw, Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2 . [all data]

Stull, 1947
Stull, Daniel R., Vapor Pressure of Pure Substances. Organic and Inorganic Compounds, Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022 . [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]

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

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Symbols used in this document:

C_p,liquid	Constant pressure heat capacity of liquid
IE (evaluated)	Recommended ionization energy
P_c	Critical pressure
T_c	Critical temperature
Δ_cH°_liquid	Enthalpy of combustion of liquid at standard conditions
Δ_fH°_gas	Enthalpy of formation of gas at standard conditions
Δ_fH°_liquid	Enthalpy of formation of liquid at standard conditions
Δ_rH°	Enthalpy of reaction at standard conditions
Δ_vapH°	Enthalpy of vaporization at standard conditions
ρ_c	Critical density

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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