Tetracyanoethylene


Gas 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:
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Δfgas164.5kcal/molN/ABaroody and Carpenter, 1972Value computed using ΔfHsolid° value of 607.1 kj/mol from Baroody and Carpenter, 1972 and ΔsubH° value of 81.0 kj/mol from Boyd, 1963.; DRB
Δfgas170.7kcal/molN/AFrankel, Amster, et al., 1966Value computed using ΔfHsolid° value of 633.0±2.0 kj/mol from Frankel, Amster, et al., 1966 and ΔsubH° value of 81.0 kj/mol from Boyd, 1963.; DRB
Δfgas168.5 ± 1.5kcal/molCcbBoyd, 1963ALS

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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Δfsolid145.1kcal/molCcbBaroody and Carpenter, 1972 
Δfsolid151.4 ± 0.5kcal/molCcbFrankel, Amster, et al., 1966 
Δfsolid149.1 ± 0.4kcal/molCcbBoyd, 1963 
Quantity Value Units Method Reference Comment
Δcsolid-716.1 ± 0.5kcal/molCcbFrankel, Amster, et al., 1966 
Δcsolid-724.98kcal/molCcbWebster, 1966 
Δcsolid-713.4 ± 0.4kcal/molCcbBoyd, 1963 

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

Quantity Value Units Method Reference Comment
Tboil496.2KN/AWeast and Grasselli, 1989BS
Quantity Value Units Method Reference Comment
Tfus472.0KN/ARadomska and Radomski, 1991Uncertainty assigned by TRC = 0.2 K; TRC
Quantity Value Units Method Reference Comment
Δsub19.4kcal/molVBoyd, 1963ALS
Δsub19.4kcal/molN/ABoyd, 1963DRB

Enthalpy of sublimation

ΔsubH (kcal/mol) Temperature (K) Method Reference Comment
19.5348.AStephenson and Malanowski, 1987Based on data from 333. to 371. K.; AC
20.1302.TE,MEDe Wit, Van Miltenburg, et al., 1983Based on data from 290. to 312. K.; AC
19.4 ± 1.4350.N/ABoyd, 1963, 2See also Cox and Pilcher, 1970.; AC

Enthalpy of fusion

ΔfusH (kcal/mol) Temperature (K) Reference Comment
5.956472.2Radomska and Radomski, 1991AC

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:


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

1,3-Cyclopentadiene + Tetracyanoethylene = Bicyclo[2.2.1]hept-5-ene-2,2,3,3-tetracarbonitrile

By formula: C5H6 + C6N4 = C11H6N4

Quantity Value Units Method Reference Comment
Δr-26.8kcal/molKinSamuilov, Bukharov, et al., 1981liquid phase; solvent: Chorobenzene
Δr-25.56 ± 0.70kcal/molCmRogers, 1972liquid phase

C21H12N4 = Tetracyanoethylene + Anthracene, 9-methyl-

By formula: C21H12N4 = C6N4 + C15H12

Quantity Value Units Method Reference Comment
Δr14.9kcal/molKinLotfi and Roberts, 1979liquid phase; solvent: CCl4; Spectrophotometrically

3-Methyl-4-cyclohexene-1,1,2,2-tetracarbonitrile = Tetracyanoethylene + Isoprene

By formula: C11H8N4 = C6N4 + C5H8

Quantity Value Units Method Reference Comment
Δr37.6 ± 0.8kcal/molCmRogers, 1971solid phase; Heat of formation derived by 77PED/RYL

Tetracyanoethylene + Isoprene = 3-Methyl-4-cyclohexene-1,1,2,2-tetracarbonitrile

By formula: C6N4 + C5H8 = C11H8N4

Quantity Value Units Method Reference Comment
Δr-37.6 ± 0.8kcal/molCmRogers, 1971liquid phase; solvent: Dichloromethane

Benzene, (1-methoxyethenyl)- + Tetracyanoethylene = 1,1,2,2-Cyclobutanetetracarbonitrile, 3-methoxy-3-phenyl-

By formula: C9H10O + C6N4 = C15H10N4O

Quantity Value Units Method Reference Comment
Δr-12.4kcal/molCmSolomonov, Antipin, et al., 1979liquid phase; solvent: methylene chloride

1,3-Butadiene, 2,3-dimethyl- + Tetracyanoethylene = C12H10N4

By formula: C6H10 + C6N4 = C12H10N4

Quantity Value Units Method Reference Comment
Δr-39.57 ± 0.44kcal/molCmRogers, 1972liquid phase

1,3-Cyclohexadiene + Tetracyanoethylene = Bicyclo[2.2.2]oct-5-ene-2,2,3,3-tetracarbonitrile

By formula: C6H8 + C6N4 = C12H8N4

Quantity Value Units Method Reference Comment
Δr-28.90 ± 0.77kcal/molCmRogers, 1972liquid phase

C12H10N4 = 1,3-Butadiene, 2,3-dimethyl- + Tetracyanoethylene

By formula: C12H10N4 = C6H10 + C6N4

Quantity Value Units Method Reference Comment
Δr39.57 ± 0.44kcal/molCmRogers, 1972solid phase

Bicyclo[2.2.2]oct-5-ene-2,2,3,3-tetracarbonitrile = 1,3-Cyclohexadiene + Tetracyanoethylene

By formula: C12H8N4 = C6H8 + C6N4

Quantity Value Units Method Reference Comment
Δr28.90 ± 0.77kcal/molCmRogers, 1972solid phase

Bicyclo[2.2.1]hept-5-ene-2,2,3,3-tetracarbonitrile = 1,3-Cyclopentadiene + Tetracyanoethylene

By formula: C11H6N4 = C5H6 + C6N4

Quantity Value Units Method Reference Comment
Δr25.56 ± 0.70kcal/molCmRogers, 1972solid phase

9,10-Dihydro-9,10-ethanoanthracene-11,11,12,12-tetracarbonitrile = Anthracene + Tetracyanoethylene

By formula: C20H10N4 = C14H10 + C6N4

Quantity Value Units Method Reference Comment
Δr9.69 ± 0.50kcal/molCmRogers, 1972solid phase

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
3.160 ± 0.020LPESKhuseynov, Fontana, et al., 2012B
3.17 ± 0.20IMREChowdhury and Kebarle, 1986ΔGea(423 K) = -73.0 kcal/mol; ΔSea (estimated) = 0. eu.; B
2.30 ± 0.30LPDLyons and Palmer, 1976B
1.70 ± 0.30LPDLyons and Palmer, 1975B
2.030 ± 0.052PDLyons and Palmer, 1973B
2.884 ± 0.061SIFarragher and Page, 1967The Magnetron method, lacking mass analysis, is not considered reliable.; B

Ionization energy determinations

IE (eV) Method Reference Comment
11.765 ± 0.008PIKnowles and Nicholson, 1974LLK
11.67 ± 0.02PIKotov and Potapov, 1972LLK
11.79 ± 0.05PEHouk and Munchausen, 1976Vertical value; LLK

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

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


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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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-1390
NIST MS number 233488

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References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), NIST Subscription Links, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Baroody and Carpenter, 1972
Baroody, E.E.; Carpenter, G.A., Heats of formation of propellant compounds (U), Rpt. Naval Ordnance Systems Command Task No. 331-003/067-1/UR2402-001 for Naval Ordance Station, Indian Head, MD, 1972, 1-9. [all data]

Boyd, 1963
Boyd, R.H., Thermochemistry of cyanocarbons, J. Chem. Phys., 1963, 38, 2529-2535. [all data]

Frankel, Amster, et al., 1966
Frankel, M.B.; Amster, A.B.; Wilson, E.R.; McCormick, M.; McEachern, M., Jr., Synthesis and thermochemistry of tricyanomethyl and other polycyano compounds, Adv. Chem. Ser., 1966, 108-117. [all data]

Webster, 1966
Webster, O.W., Diazotetracyanocyclopentadiene, J. Am. Chem. Soc., 1966, 88, 4055-4060. [all data]

Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]

Radomska and Radomski, 1991
Radomska, M.; Radomski, R., Phase diagrams in the binary systems of tetracyanoethylene with mesitylene, durene and pentamethylbenzene, Journal of Thermal Analysis, 1991, 37, 4, 693-704, https://doi.org/10.1007/BF01913148 . [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]

De Wit, Van Miltenburg, et al., 1983
De Wit, H.G.M.; Van Miltenburg, J.C.; De Kruif, C.G., Thermodynamic properties of molecular organic crystals containing nitrogen, oxygen, and sulphur 1. Vapour pressures and enthalpies of sublimation, The Journal of Chemical Thermodynamics, 1983, 15, 7, 651-663, https://doi.org/10.1016/0021-9614(83)90079-4 . [all data]

Boyd, 1963, 2
Boyd, Richard H., Thermochemistry of Cyanocarbons, J. Chem. Phys., 1963, 38, 10, 2529, https://doi.org/10.1063/1.1733536 . [all data]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press Inc., London, 1970, 643. [all data]

Samuilov, Bukharov, et al., 1981
Samuilov, Ya.D.; Bukharov, S.V.; Konovalov, A.I., Reactivity of tetraphenylcyclopentadiene and tetracyclone in the Diels-Alder reaction with cyanoethylenes, Zh. Org. Khim., 1981, 17, 2389-2393. [all data]

Rogers, 1972
Rogers, F.E., Thermochemistry of the Diels-Alder reactions. II. Heat of addition of several dienes to tetracyanoethylene, J. Phys. Chem., 1972, 76, 106-109. [all data]

Lotfi and Roberts, 1979
Lotfi, M.; Roberts, R.M.G., Kinetics and mechanism of Diels-Alder additions of tetracyanoethylene to anthracene derivatives - I. Substituent effects, Tetrahedron, 1979, 35, 2131-2136. [all data]

Rogers, 1971
Rogers, F.E., Thermochemistry of the Diels-Alder reaction. I. Enthalpy of addition of isoprene to tetracyanoethylene, J. Phys. Chem., 1971, 75, 1734-1737. [all data]

Solomonov, Antipin, et al., 1979
Solomonov, B.N.; Antipin, I.S.; Konovalov, A.I.; Novikov, V.B., Solvation effects in the retro[2 + 2]cycloaddition reaction, Zh. Org. Khim., 1979, 15, 2466-24. [all data]

Khuseynov, Fontana, et al., 2012
Khuseynov, D.; Fontana, M.T.; Sanov, A., Photoelectron spectroscopy and photochemistry of tetracyanoethylene radical anion in the gas phase, Chem. Phys. Lett., 2012, 550, 15-18, https://doi.org/10.1016/j.cplett.2012.08.035 . [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]

Lyons and Palmer, 1976
Lyons, L.E.; Palmer, L.D., The electron affinity of tetracyanoethylene and other organic electron acceptors, Aust. J. Chem., 1976, 29, 1919. [all data]

Lyons and Palmer, 1975
Lyons, L.E.; Palmer, L.D., A Surface ionization source and quadrupole mass filter for photodetachment studies, Int. J. Mass Spectrom. Ion Phys., 1975, 16, 431. [all data]

Lyons and Palmer, 1973
Lyons, L.E.; Palmer, L.D., Photodetachment of electrons from tetracyanoethylene nNegative ions, Chem. Phys. Lett., 1973, 21, 442. [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]

Knowles and Nicholson, 1974
Knowles, D.J.; Nicholson, A.J.C., Ionization energies of formic and acetic acid monomers, J. Chem. Phys., 1974, 60, 1180. [all data]

Kotov and Potapov, 1972
Kotov, B.V.; Potapov, V.K., Ionization potentials of strong organic electron acceptors, Khim. Vys. Energ., 1972, 6, 375. [all data]

Houk and Munchausen, 1976
Houk, K.N.; Munchausen, L.L., Ionization potentials, electron affinities, reactivities of cyanoalkenes related electron-deficient alkenes. A frontier molecular orbital treatment of cyanoalkene reactivities in cycloaddition, electrophilic, nucleophilic, and radical reactions., J. Am. Chem. Soc., 1976, 98, 937. [all data]


Notes

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