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1,2-Benzenedicarbonitrile

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Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, 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
Deltafgas368.3kJ/molN/ARabinovich, Karyakin, et al., 1984Value computed using «DELTA»fHsolid° value of 281.4±1.9 kj/mol from Rabinovich, Karyakin, et al., 1984 and «DELTA»subH° value of 86.9 kj/mol from Rabinovich, Karyakin, et al., 1984.; DRB
Deltafgas367.5 ± 1.9kJ/molCcbSato-Toshima, Sakiyama, et al., 1980ALS
Deltafgas362.0kJ/molN/ASalley and Gray, 1951Value computed using «DELTA»fHsolid° value of 275.1 kj/mol from Salley and Gray, 1951 and «DELTA»subH° value of 86.9 kj/mol from Salley and Gray, 1951.; DRB

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
Deltafsolid281.4 ± 1.9kJ/molCcbRabinovich, Karyakin, et al., 1984Heat of combustion is not reported; ALS
Deltafsolid280.6 ± 1.2kJ/molCcbSato-Toshima, Sakiyama, et al., 1980ALS
Deltafsolid275.1kJ/molCcbSalley and Gray, 1951correction of Salley and Gray, 1948; ALS
Quantity Value Units Method Reference Comment
Deltacsolid-4000.36 ± 0.67kJ/molCcbSato-Toshima, Sakiyama, et al., 1980ALS
Deltacsolid-3994.9kJ/molCcbSalley and Gray, 1951correction of Salley and Gray, 1948; ALS
Quantity Value Units Method Reference Comment
solid,1 bar192.4J/mol*KN/ARabinovich, Karyakin, et al., 1984, 2DH
solid,1 bar192.4J/mol*KN/AKaryakin, Shvetsova, et al., 1982DH

Constant pressure heat capacity of solid

Cp,solid (J/mol*K) Temperature (K) Reference Comment
161.3298.15Rabinovich, Karyakin, et al., 1984, 2T = 13 to 500 K.; DH
161.3298.15Karyakin, Shvetsova, et al., 1982T = 13 to 480 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:
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
Tfus414.KN/ABuckingham and Donaghy, 1982BS
Tfus412.92KN/AWitschonke, 1954Uncertainty assigned by TRC = 0.25 K; TRC
Tfus413.05KN/AWitschonke, 1954Uncertainty assigned by TRC = 0.2 K; TRC
Quantity Value Units Method Reference Comment
Ttriple414.0KN/ARabinovich, Nistratov, et al., 1984Uncertainty assigned by TRC = 0.2 K; TRC
Ttriple414.0KN/AKaryikin, Shvetsova, et al., 1982Uncertainty assigned by TRC = 0.1 K; TRC
Quantity Value Units Method Reference Comment
Deltasub86.9 ± 1.5kJ/molVSato-Toshima, Sakiyama, et al., 1980ALS
Deltasub86.9kJ/molN/ASato-Toshima, Sakiyama, et al., 1980DRB
Deltasub86.9 ± 1.5kJ/molGSSato-Toshima, Sakiyama, et al., 1980AC

Reduced pressure boiling point

Tboil (K) Pressure (bar) Reference Comment
423. - 425.0.013Buckingham and Donaghy, 1982BS

Enthalpy of fusion

DeltafusH (kJ/mol) Temperature (K) Reference Comment
20.000414.0Rabinovich, Karyakin, et al., 1984, 2DH
20.000414.0Karyakin, Shvetsova, et al., 1982DH
20.0414.1Karyakin, Shvetsova, et al., 1982, 2AC

Entropy of fusion

DeltafusS (J/mol*K) Temperature (K) Reference Comment
48.26414.0Rabinovich, Karyakin, et al., 1984, 2DH
48.26414.0Karyakin, Shvetsova, et al., 1982DH

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:


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 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 ± 0.087TDEqChowdhury and Kebarle, 1986«DELTA»Gea(423 K) = -22.3 kcal/mol; «DELTA»Sea (estimated) = +1.0 eu.; B
1.11 ± 0.13SIFarragher and Page, 1967The Magnetron method, lacking mass analysis, is not considered reliable.; B

Ionization energy determinations

IE (eV) Method Reference Comment
9.9PEPalmer, Moyes, et al., 1980LLK
9.9PENeijzen and DeLange, 1978LLK
10.27PEPalmer, Moyes, et al., 1980Vertical value; LLK
10.10PENeijzen and DeLange, 1978Vertical value; LLK

Mass spectrum (electron ionization)

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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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Mass spectrum
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Additional Data

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Owner NIST Mass Spectrometry Data Center
Collection (C) 2014 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin Japan AIST/NIMC Database- Spectrum MS-NW- 408
NIST MS number 228962

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Gas Chromatography

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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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Normal alkane RI, non-polar column, temperature ramp

View large format table.

Column type Active phase I Reference Comment
CapillaryZB-51304.Kluchinsky, Sheely, et al., 200230. m/0.25 mm/0.25 «mu»m, He, 10. K/min, 200. C @ 2. min; Tstart: 40. C

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, 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]

Salley and Gray, 1948
Salley, D.J.; Gray, J.B., Heats of combustion of some organic nitrogen compounds, J. Am. Chem. Soc., 1948, 70, 2650-2653. [all data]

Rabinovich, Karyakin, et al., 1984, 2
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]

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]

Karyakin, Shvetsova, et al., 1982, 2
Karyakin, N.V.; Shvetsova, K.G.; Dzharimova, E.S., Termodin. Org. Soedin., 1982, 33. [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]

Kluchinsky, Sheely, et al., 2002
Kluchinsky, T.A., Jr.; Sheely, M.V.; Savage, P.B.; Smith, P.A., Formation of 2-chlorobenzylidenemalononitrile (CS riot control agent) thermal degradation products at elevated temperatures, J. Chromatogr. A, 2002, 952, 1-2, 205-213, https://doi.org/10.1016/S0021-9673(02)00096-1 . [all data]


Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, References