Propiolonitrile

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

Quantity Value Units Method Reference Comment
Δfgas354.kJ/molIonHarland, 1986Appearance potential

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 by: Robert L. Brown and Stephen E. Stein

Quantity Value Units Method Reference Comment
Tboil315.7KN/AWeast and Grasselli, 1989 

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 as indicated in comments:
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
B - John E. Bartmess
ALS - 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

CH6N+ + Propiolonitrile = (CH6N+ • Propiolonitrile)

By formula: CH6N+ + C3HN = (CH6N+ • C3HN)

Quantity Value Units Method Reference Comment
Δr100.kJ/molPHPMSSpeller and Meot-Ner (Mautner), 1985gas phase; Entropy change calculated or estimated, CD3NH3+; M
Quantity Value Units Method Reference Comment
Δr100.J/mol*KN/ASpeller and Meot-Ner (Mautner), 1985gas phase; Entropy change calculated or estimated, CD3NH3+; M

Free energy of reaction

ΔrG° (kJ/mol) T (K) Method Reference Comment
48.5500.PHPMSSpeller and Meot-Ner (Mautner), 1985gas phase; Entropy change calculated or estimated, CD3NH3+; M

C3N- + Hydrogen cation = Propiolonitrile

By formula: C3N- + H+ = C3HN

Quantity Value Units Method Reference Comment
Δr1467. ± 8.8kJ/molG+TSTaft, Abboud, et al., 1988gas phase; B
Δr1439. ± 15.kJ/molEIAEGraupner, Merrigan, et al., 2006gas phase; B
Quantity Value Units Method Reference Comment
Δr1435. ± 8.4kJ/molIMRETaft, Abboud, et al., 1988gas phase; B

(CAS Reg. No. 36259-97-9 • 4294967295Propiolonitrile) + Propiolonitrile = CAS Reg. No. 36259-97-9

By formula: (CAS Reg. No. 36259-97-9 • 4294967295C3HN) + C3HN = CAS Reg. No. 36259-97-9

Quantity Value Units Method Reference Comment
Δr319. ± 13.kJ/molN/ABartmess, 1980gas phase; value altered from reference due to change in acidity scale; B

NH4+ + Propiolonitrile = (NH4+ • Propiolonitrile)

By formula: H4N+ + C3HN = (H4N+ • C3HN)

Quantity Value Units Method Reference Comment
Δr95.8kJ/molPHPMSSpeller and Meot-Ner (Mautner), 1985gas phase; M
Quantity Value Units Method Reference Comment
Δr94.6J/mol*KPHPMSSpeller and Meot-Ner (Mautner), 1985gas phase; M

C3H2N+ + Propiolonitrile = (C3H2N+ • Propiolonitrile)

By formula: C3H2N+ + C3HN = (C3H2N+ • C3HN)

Quantity Value Units Method Reference Comment
Δr115.kJ/molPHPMSSpeller and Meot-Ner (Mautner), 1985gas phase; M
Quantity Value Units Method Reference Comment
Δr108.J/mol*KPHPMSSpeller and Meot-Ner (Mautner), 1985gas phase; M

Propiolonitrile + 1,3 Diphenylisobenzofuran = C23H17NO

By formula: C3HN + C20H14O = C23H17NO

Quantity Value Units Method Reference Comment
Δr-117.kJ/molKinSamuilov, Nurullina, et al., 1983liquid phase; solvent: Nonaquous; ALS

References

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

Harland, 1986
Harland, P.W., Appearance energies and enthalpies of formation from ionization of cyanoacetylene by "Monochromatic" electron impact, Int. J. Mass Spectrom. Ion Processes, 1986, 70, 231-236. [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]

Speller and Meot-Ner (Mautner), 1985
Speller, C.V.; Meot-Ner (Mautner), M., The Ionic Hydrogen Bond and Ion Solvation. 3. Bonds Involving Cyanides. Correlations with Proton Affinites, J. Phys. Chem., 1985, 81, 24, 5217, https://doi.org/10.1021/j100270a020 . [all data]

Taft, Abboud, et al., 1988
Taft, R.W.; Abboud, J.L.M.; Anvia, F.; Berthelot, M.; Fujio, M.; Gal, J.-F.; Headley, A.D.; Henderson, W.G., Regarding the Inherent Dependence of Resonance Effects of Strongly Conjugated Substituents on Electron Demand, J. Am. Chem. Soc., 1988, 110, 6, 1797, https://doi.org/10.1021/ja00214a023 . [all data]

Graupner, Merrigan, et al., 2006
Graupner, K.; Merrigan, T.L.; Field, T.A.; Youngs, T.G.A.; Marr, P.C., Dissociative Electron Attachment to HCCCN, New J. Phys., 2006, , 117 (2006), 7, 117, https://doi.org/10.1088/1367-2630/8/7/117 . [all data]

Bartmess, 1980
Bartmess, J.E., Solvent effects on ion-molecule reactions. Vinyl anions vs. conjugate addition, J. Am. Chem. Soc., 1980, 102, 2483. [all data]

Samuilov, Nurullina, et al., 1983
Samuilov, Ya.D.; Nurullina, R.L.; Konovalov, A.I., Thermochemical and kinetic study of the Diels-Alder reaction with ethylene and acetylene dienophiles, Zh. Org. Khim., 1983, 19, 1431-1435. [all data]


Notes

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