1,4-Benzenedicarbonitrile
- Formula: C8H4N2
- Molecular weight: 128.1308
- IUPAC Standard InChI: InChI=1S/C8H4N2/c9-5-7-1-2-8(6-10)4-3-7/h1-4H
- IUPAC Standard InChIKey: BHXFKXOIODIUJO-UHFFFAOYSA-N
- CAS Registry Number: 623-26-7
- Chemical structure:
This structure is also available as a 2d Mol file - Other names: Terephthalonitrile; p-Benzenedinitrile; p-Dicyanobenzene; p-Phthalodinitrile; Terephthalic acid dinitrile; Terephthalodinitrile; 1,4-Dicyanobenzene; 4-Cyanobenzonitrile; Terephthalonitrile (di); p-Pdn; Nitril kyseliny tereftalove; Tereftalodinitril; 1,4-Benzodinitrile; 1,4-Benzendikarbonitril; Tereftalonitril; p-Phthalonitrile; p-Cyanobenzonitrile; NSC 144977; NSC 78439
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Gas phase thermochemistry data
Go To: Top, Gas phase ion energetics data, IR Spectrum, 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
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | 85.64 ± 0.53 | kcal/mol | Ccb | Acree, Tucker, et al., 1992 | Author was aware that data differs from previously reported values |
| ΔfH°gas | 85.35 ± 0.45 | kcal/mol | Ccb | Sato-Toshima, Sakiyama, et al., 1980 |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, IR Spectrum, 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:
HL - Edward P. Hunter and Sharon G. Lias
Data compiled as indicated in comments:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
B - John E. Bartmess
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| Proton affinity (review) | 186.2 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
| Quantity | Value | Units | Method | Reference | Comment |
| Gas basicity | 179.7 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Electron affinity determinations
| EA (eV) | Method | Reference | Comment |
|---|---|---|---|
| 1.093 ± 0.087 | TDEq | Chowdhury and Kebarle, 1986 | ΔGea(423 K) = -25.8 kcal/mol; ΔSea = +1.0 eu.; B |
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 10.10 | PE | Neijzen and DeLange, 1978 | LLK |
| 10.1 | PE | Palmer, Moyes, et al., 1980 | Vertical value; LLK |
| 10.10 | PE | Neijzen and DeLange, 1978 | Vertical value; LLK |
IR Spectrum
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, References, Notes
Data compiled by: Coblentz Society, Inc.
- SOLID (MINERAL OIL MULL); Not specified, most likely a prism, grating, or hybrid spectrometer.; DIGITIZED BY NIST FROM HARD COPY; 4 cm-1 resolution
- SOLID (NUJOL MULL) $$SPECTRAL CONTAMINATION DUE TO OIL AROUND 2900, 1460, 1380, 720 CM-1; DOW KBr FOREPRISM-GRATING; DIGITIZED BY COBLENTZ SOCIETY (BATCH I) FROM HARD COPY; 2 cm-1 resolution
References
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, IR Spectrum, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Acree, Tucker, et al., 1992
Acree, W.E., Jr.; Tucker, S.A.; Pilcher, G.,
Enthalpies of combustion of 1,4-dicyanobenzene di-N-oxide and 1,4-dicyanobenzene: the mean dissociation enthalpy of the (N-O) bonds,
J. Chem. Thermodyn., 1992, 24, 213-216. [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]
Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G.,
Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update,
J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018
. [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]
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]
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]
Notes
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, IR Spectrum, 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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