1,2-Benzenedicarbonitrile
- Formula: C8H4N2
- Molecular weight: 128.1308
- IUPAC Standard InChI: InChI=1S/C8H4N2/c9-5-7-3-1-2-4-8(7)6-10/h1-4H
- IUPAC Standard InChIKey: XQZYPMVTSDWCCE-UHFFFAOYSA-N
- CAS Registry Number: 91-15-6
- 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: Phthalonitrile; o-Benzenedicarbonitrile; o-Cyanobenzonitrile; o-Dicyanobenzene; Phthalodinitrile; 1,2-Dicyanobenzene; o-Phthalodinitrile; o-PDN; Phthalic acid dinitrile; USAF ND-09; 1,2-Benzodinitrile; 1,2-Benzendikarbonitril; Ftalodinitril; Ftalonitril; o-Benzenedinitrile; NSC 17562
- Permanent link for this species. Use this link for bookmarking this species for future reference.
- Information on this page:
- Other data available:
- Options:
Data at NIST subscription sites:
NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.
Phase change data
Go To: Top, 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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos
DH - Eugene S. Domalski and Elizabeth D. Hearing
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| Tfus | 414. | K | N/A | Buckingham and Donaghy, 1982 | BS |
| Tfus | 412.92 | K | N/A | Witschonke, 1954 | Uncertainty assigned by TRC = 0.25 K; TRC |
| Tfus | 413.05 | K | N/A | Witschonke, 1954 | Uncertainty assigned by TRC = 0.2 K; TRC |
| Quantity | Value | Units | Method | Reference | Comment |
| Ttriple | 414.0 | K | N/A | Rabinovich, Nistratov, et al., 1984 | Uncertainty assigned by TRC = 0.2 K; TRC |
| Ttriple | 414.0 | K | N/A | Karyikin, Shvetsova, et al., 1982 | Uncertainty assigned by TRC = 0.1 K; TRC |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔsubH° | 20.8 ± 0.36 | kcal/mol | V | Sato-Toshima, Sakiyama, et al., 1980 | ALS |
| ΔsubH° | 20.8 | kcal/mol | N/A | Sato-Toshima, Sakiyama, et al., 1980 | DRB |
| ΔsubH° | 20.8 ± 0.36 | kcal/mol | GS | Sato-Toshima, Sakiyama, et al., 1980 | AC |
Reduced pressure boiling point
| Tboil (K) | Pressure (atm) | Reference | Comment |
|---|---|---|---|
| 423. to 425. | 0.013 | Buckingham and Donaghy, 1982 | BS |
Enthalpy of fusion
| ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 4.7801 | 414.0 | Rabinovich, Karyakin, et al., 1984 | DH |
| 4.7801 | 414.0 | Karyakin, Shvetsova, et al., 1982 | DH |
| 4.78 | 414.1 | Karyakin, Shvetsova, et al., 1982, 2 | AC |
Entropy of fusion
| ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 11.53 | 414.0 | Rabinovich, Karyakin, et al., 1984 | DH |
| 11.53 | 414.0 | Karyakin, Shvetsova, et al., 1982 | DH |
References
Go To: Top, Phase change data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Buckingham and Donaghy, 1982
Buckingham, J.; Donaghy, S.M.,
Dictionary of Organic Compounds: Fifth Edition, Chapman and Hall, New York, 1982, 1. [all data]
Witschonke, 1954
Witschonke, C.R.,
Freezing point and purity data for some organic compounds,
Anal. Chem., 1954, 26, 562-4. [all data]
Rabinovich, Nistratov, et al., 1984
Rabinovich, I.B.; Nistratov, V.P.; Babinkov, A.G.; Siling, S.A.; Ponomarev, I.I.; Vinogradova, S.V.,
Thermodynamics of the condensation of o-phthalic acid dinitrile with m-phenylenediamine,
Izv. Akad. Nauk SSSR, 1984, 1984, 779. [all data]
Karyikin, Shvetsova, et al., 1982
Karyikin, N.V.; Shvetsova, K.G.; Dzharimova, E.S.,
Thermodynamic properties of o-phthalic acid dinitrile,
Termodin. Org. Soedin., 1982, 33-37. [all data]
Sato-Toshima, Sakiyama, et al., 1980
Sato-Toshima, T.; Sakiyama, M.; Seki, S.,
Thermochemical estimation of destabilization energies of 1,2-, 1,3-, and 1,4-dicyanobenzenes due to interactions between substituents. Appendix: Dipole moments in solution of the dicyanobenzenes,
Bull. Chem. Soc. Jpn., 1980, 53, 2762-2767. [all data]
Rabinovich, Karyakin, et al., 1984
Rabinovich, I.B.; Karyakin, N.V.; Dzharimova, E.S.; Siling, S.A.; Ponomarev, I.I.; Vinogradova, S.V.,
Thermodynamics of the condensation of o-phthalic acid dinitrile with m-phenylenediamine, Izv. Akad. Nauk SSSR,
Ser. Khim., 1984, (4), 779-787. [all data]
Karyakin, Shvetsova, et al., 1982
Karyakin, N.V.; Shvetsova, K.G.; Dzharimova, E.S.,
Thermodynamic properties of o-phthalic acid dinitrile, 1982, Termodin. [all data]
Karyakin, Shvetsova, et al., 1982, 2
Karyakin, N.V.; Shvetsova, K.G.; Dzharimova, E.S.,
Termodin. Org. Soedin., 1982, 33. [all data]
Notes
Go To: Top, Phase change data, References
- Symbols used in this document:
Tboil Boiling point Tfus Fusion (melting) point Ttriple Triple point temperature ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔsubH° Enthalpy of sublimation at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
- The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
- Customer support for NIST Standard Reference Data products.