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Propiolonitrile

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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+ bullet Propiolonitrile)

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

Quantity Value Units Method Reference Comment
Deltar100.kJ/molPHPMSSpeller and Meot-Ner (Mautner), 1985gas phase; Entropy change calculated or estimated, CD3NH3+; M
Quantity Value Units Method Reference Comment
Deltar100.J/mol*KN/ASpeller and Meot-Ner (Mautner), 1985gas phase; Entropy change calculated or estimated, CD3NH3+; M

Free energy of reaction

DeltarG° (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
Deltar1467. ± 8.8kJ/molG+TSTaft, Abboud, et al., 1988gas phase; B
Deltar1439. ± 15.kJ/molEIAEGraupner, Merrigan, et al., 2006gas phase; B
Quantity Value Units Method Reference Comment
Deltar1435. ± 8.4kJ/molIMRETaft, Abboud, et al., 1988gas phase; B

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

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

Quantity Value Units Method Reference Comment
Deltar319. ± 13.kJ/molN/ABartmess, 1980gas phase; value altered from reference due to change in acidity scale; B

NH4+ + Propiolonitrile = (NH4+ bullet Propiolonitrile)

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

Quantity Value Units Method Reference Comment
Deltar95.8kJ/molPHPMSSpeller and Meot-Ner (Mautner), 1985gas phase; M
Quantity Value Units Method Reference Comment
Deltar94.6J/mol*KPHPMSSpeller and Meot-Ner (Mautner), 1985gas phase; M

C3H2N+ + Propiolonitrile = (C3H2N+ bullet Propiolonitrile)

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

Quantity Value Units Method Reference Comment
Deltar115.kJ/molPHPMSSpeller and Meot-Ner (Mautner), 1985gas phase; M
Quantity Value Units Method Reference Comment
Deltar108.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
Deltar-117.kJ/molKinSamuilov, Nurullina, et al., 1983liquid phase; solvent: Nonaquous; ALS

References

Go To: Top, Reaction thermochemistry data, Notes

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

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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