Benzene, 1-chloro-3-isocyanato-
- Formula: C7H4ClNO
- Molecular weight: 153.566
- IUPAC Standard InChI: InChI=1S/C7H4ClNO/c8-6-2-1-3-7(4-6)9-5-10/h1-4H
- IUPAC Standard InChIKey: HHIRBXHEYVDUAM-UHFFFAOYSA-N
- CAS Registry Number: 2909-38-8
- 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, m-chlorophenyl ester; m-Chlorophenyl isocyanate; 1-Chloro-3-isocyanatobenzene; 3-Chlorophenyl isocyanate; 3-Chloroisocyanatobenzene; m-Chlorfenylisokyanat
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Condensed 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
DH - Eugene S. Domalski and Elizabeth D. Hearing
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔcH°liquid | -783. ± 15. | kcal/mol | Ccb | Zalikin, Kochetkov, et al., 1965 | ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔfH°solid | -19.8 ± 1.0 | kcal/mol | Ccb | Selivanov and Konstantinov, 1975 | ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°solid | -780.0 ± 1.0 | kcal/mol | Ccb | Selivanov and Konstantinov, 1975 | ALS |
Constant pressure heat capacity of liquid
| Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 44.69 | 294.2 | Zalikin, Kochetkov, et al., 1965 | T = 294, 323 K.; DH |
Phase change 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
AC - William E. Acree, Jr., James S. Chickos
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔvapH° | 12.90 ± 0.05 | kcal/mol | V | Zalikin, Kochetkov, et al., 1965 | ALS |
Enthalpy of vaporization
| ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 12.7 | 359. | A | Stephenson and Malanowski, 1987 | Based on data from 344. to 432. K. See also Goldberg, Gorbushchenkov, et al., 1964.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (atm)
T = temperature (K)
View plot Requires a JavaScript / HTML 5 canvas capable browser.
| Temperature (K) | A | B | C | Reference | Comment |
|---|---|---|---|---|---|
| 303. to 388. | 2.85663 | 1067.251 | -126.851 | Zalikin, Kochetkov, et al., 1965 | Coefficents calculated by NIST from author's data. |
| 344. to 431.5 | 3.59335 | 1325.111 | -111.257 | Goldberg, Gorbushchenkov, et al., 1964, 2 | Coefficents calculated by NIST from author's data. |
Reaction 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 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
=
+
By formula: C13H10Cl2N2O = C6H6ClN + C7H4ClNO
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 29.2 ± 1.3 | kcal/mol | Eqk | Chimishkyan, Svetlova, et al., 1984 | solid phase; Dissociation |
=
+
By formula: C9H11ClN2O = C2H7N + C7H4ClNO
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 35.37 ± 0.43 | kcal/mol | Eqk | Chimishkyan, Svetlova, et al., 1984 | solid phase; Dissociation |
Gas phase ion energetics 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 by: Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 9.0 ± 0.1 | PE | Neijzen and DeLange, 1980 | Vertical value |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction 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.
Zalikin, Kochetkov, et al., 1965
Zalikin, A.A.; Kochetkov, V.L.; Strepikheev, Yu.A.,
Some physical and physicochemical constants of m- and p-chloroaniline and of m- and p-chlorophenyl isocyanate,
Khim. Prom. (Moscow), 1965, 41, 338. [all data]
Selivanov and Konstantinov, 1975
Selivanov, V.D.; Konstantinov, I.I.,
Thermochemistry of chloroaryl isocyanates,
Russ. J. Phys. Chem. (Engl. Transl.), 1975, 49, 620-621. [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]
Goldberg, Gorbushchenkov, et al., 1964
Goldberg, N.A.; Gorbushchenkov, V.A.; Teplova, Z.G.,
Zh. Prikl. Khim. (S.-Peterburg), 1964, 37, 745. [all data]
Goldberg, Gorbushchenkov, et al., 1964, 2
Goldberg, N.A.; Gorbushchenkov, V.A.; Teplova, Z.G.,
Some Physical Property of m-Chlorphenyl Isocyonate,
Zh. Prikl. Khim. (Leningrad), 1964, 37, 745-747. [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]
Neijzen and DeLange, 1980
Neijzen, B.J.M.; DeLange, C.A.,
Photoelectron spectroscopy of some thiocyanates, isocyanates and isothiocyanates,
J. Electron Spectrosc. Relat. Phenom., 1980, 18, 179. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics 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 ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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