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
View 3d structure (requires JavaScript / HTML 5) - 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
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Gas phase thermochemistry data
Go To: Top, 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:
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | 368.3 | kJ/mol | N/A | Rabinovich, Karyakin, et al., 1984 | Value computed using ΔfHsolid° value of 281.4±1.9 kj/mol from Rabinovich, Karyakin, et al., 1984 and ΔsubH° value of 86.9 kj/mol from Rabinovich, Karyakin, et al., 1984.; DRB |
| ΔfH°gas | 367.5 ± 1.9 | kJ/mol | Ccb | Sato-Toshima, Sakiyama, et al., 1980 | ALS |
| ΔfH°gas | 362.0 | kJ/mol | N/A | Salley and Gray, 1951 | Value computed using ΔfHsolid° value of 275.1 kj/mol from Salley and Gray, 1951 and ΔsubH° value of 86.9 kj/mol from Salley and Gray, 1951.; DRB |
Gas phase ion energetics data
Go To: Top, Gas 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 compiled as indicated in comments:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
B - John E. Bartmess
Electron affinity determinations
| EA (eV) | Method | Reference | Comment |
|---|---|---|---|
| 0.954 ± 0.087 | TDEq | Chowdhury and Kebarle, 1986 | ΔGea(423 K) = -22.3 kcal/mol; ΔSea (estimated) = +1.0 eu.; B |
| 1.11 ± 0.13 | SI | Farragher and Page, 1967 | The Magnetron method, lacking mass analysis, is not considered reliable.; B |
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 9.9 | PE | Palmer, Moyes, et al., 1980 | LLK |
| 9.9 | PE | Neijzen and DeLange, 1978 | LLK |
| 10.27 | PE | Palmer, Moyes, et al., 1980 | Vertical value; LLK |
| 10.10 | PE | Neijzen and DeLange, 1978 | Vertical value; LLK |
References
Go To: Top, Gas 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.
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 condensation of phthalonitrile with m-phenylenediamine,
Bull. Acad. Sci. USSR, Div. Chem. Sci., 1984, 716-723. [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]
Salley and Gray, 1951
Salley, D.J.; Gray, J.B.,
Heats of combustion of some organic nitrogen compounds,
J. Am. Chem. Soc., 1951, 73, 5925. [all data]
Chowdhury and Kebarle, 1986
Chowdhury, S.; Kebarle, P.,
Electron affinities of di- and tetracyanoethylene and cyanobenzenes based on measurements of gas-phase electron transfer equilibria,
J. Am. Chem. Soc., 1986, 108, 5453. [all data]
Farragher and Page, 1967
Farragher, A.L.; Page, F.M.,
Experimental Determination of Electron Affinities. Part 11. - Electron Capture by Some Cyanocarbons and Related Compounds,
Trans. Farad. Soc., 1967, 63, 2369, https://doi.org/10.1039/tf9676302369
. [all data]
Palmer, Moyes, et al., 1980
Palmer, M.H.; Moyes, W.; Spiers, M.,
The electronic structure of substituted benzenes: Ab initio calculations and photoelectron spectra for benzonitrile, the tolunitriles, fluorobenzonitriles, dicyanobenzenes and ethynylbenzene,
J. Mol. Struct., 1980, 62, 165. [all data]
Neijzen and DeLange, 1978
Neijzen, B.J.M.; DeLange, C.A.,
Photoelectron spectroscopy of mono-dicyanobenzenes their perfluoro derivatives,
J. Electron Spectrosc. Relat. Phenom., 1978, 14, 187. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
EA Electron affinity ΔfH°gas Enthalpy of formation of gas at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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