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

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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

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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
L - Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

View reactions leading to C3HN+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
IE (evaluated)11.62 ± 0.03eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)751.2kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity720.5kJ/molN/AHunter and Lias, 1998HL

Electron affinity determinations

EA (eV) Method Reference Comment
1.040 ± 0.050LPESGoebbert, Khuseynov, et al., 2010Stated electron affinity is the Vertical Detachment Energy; B
2.56 ± 0.22R-AHeni and Illenberger, 1986From CH2=CHCN. Isomer? G3MP2B3 calculations indicate an EA of ca. 0.05 eV; B

Ionization energy determinations

IE (eV) Method Reference Comment
11.56 ± 0.04EIHarland, 1986, 2LBLHLM
11.64 ± 0.01PIOkabe and Dibeler, 1973LLK
11.6SNarayan, 1972LLK
11.60 ± 0.01PEBaker and Turner, 1968RDSH
11.6 ± 0.2EIDibeler, Reese, et al., 1961RDSH
11.75PEAsbrink, Von Niessen, et al., 1980Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
CH+21.9 ± 0.3?EIDibeler, Reese, et al., 1961RDSH
CN+19.96 ± 0.08C2HEIHarland, 1986, 2LBLHLM
CN+19.8 ± 0.2C2HEIDibeler, Reese, et al., 1961RDSH
C2+18.6 ± 0.2?EIDibeler, Reese, et al., 1961RDSH
C2H+18.84 ± 0.08CNEIHarland, 1986, 2LBLHLM
C2H+18.19 ± 0.04CNPIOkabe and Dibeler, 1973LLK
C2H+19.0 ± 0.2CNEIDibeler, Reese, et al., 1961RDSH
C2N+18.0 ± 0.5CHEIDibeler, Reese, et al., 1961RDSH
C3+24.5 ± 0.5?EIDibeler, Reese, et al., 1961RDSH
C3H+17.76 ± 0.08NEIHarland, 1986, 2LBLHLM
C3H+18.0 ± 0.2NEIDibeler, Reese, et al., 1961RDSH
C3N+17.78 ± 0.08HEIHarland, 1986, 2LBLHLM
C3N+18.2 ± 0.3HEIDibeler, Reese, et al., 1961RDSH

De-protonation reactions

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

IR Spectrum

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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

Gas Phase Spectrum

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IR spectrum
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Additional Data

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Owner NIST Standard Reference Data Program
Collection (C) 2018 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin NIST Mass Spectrometry Data Center
State gas
Instrument HP-GC/MS/IRD

This IR spectrum is from the NIST/EPA Gas-Phase Infrared Database .


Gas Chromatography

Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, 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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Kovats' RI, non-polar column, isothermal

View large format table.

Column type Active phase Temperature (C) I Reference Comment
CapillaryCP Sil 5 CB20.447.6Do and Raulin, 199225. m/0.15 mm/2. μm, H2
CapillaryPoraPLOT Q100.421.Do and Raulin, 198910. m/0.32 mm/10. μm, H2
CapillaryPoraPLOT Q160.424.Do and Raulin, 198910. m/0.32 mm/10. μm, H2

References

Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Gas Chromatography, Notes

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]

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]

Goebbert, Khuseynov, et al., 2010
Goebbert, D.J.; Khuseynov, D.; Sanov, A., Photoelectron Imiaging Spectrum of Cyanovinylidene and Cyanoacetylene anion, J. Phys. Chem. A, 2010, 114, 6, 2259, https://doi.org/10.1021/jp9106102 . [all data]

Heni and Illenberger, 1986
Heni, M.; Illenberger, E., Electron attachment by saturated nitriles. Acrylonitrile (CH2H3CN), and benzonitrile (C6H5CN), Int. J. Mass Spectrom. Ion Phys., 1986, 73, 127. [all data]

Harland, 1986, 2
Harland, P.W., Appearance energies and enthalpies of formation from ionization of cyanoacetylene by "monochromatic" electron impact, Int. J. Mass Spectrom. Ion Phys., 1986, 70, 231. [all data]

Okabe and Dibeler, 1973
Okabe, H.; Dibeler, V.H., Photon impact studies of C2HCN and CH3CN in the vacuum ultraviolet; heats of formation of C2H and CH3CN, J. Chem. Phys., 1973, 59, 2430. [all data]

Narayan, 1972
Narayan, B., Spectra and ionization potential of cyanoacetylene, Proc. Indian Acad. Sci. Sect. A, 1972, 75, 92. [all data]

Baker and Turner, 1968
Baker, C.; Turner, D.W., High resolution molecular photoelectron spectroscopy. III.Acetylenes and azaacetylenes, Proc. Roy. Soc. (London), 1968, A308, 19. [all data]

Dibeler, Reese, et al., 1961
Dibeler, V.H.; Reese, R.M.; Franklin, J.L., Mass spectrometric study of cyanogen and cyanoacetylenes, J. Am. Chem. Soc., 1961, 83, 1813. [all data]

Asbrink, Von Niessen, et al., 1980
Asbrink, L.; Von Niessen, W.; Bieri, G., 30.4-nm He(II) photoelectron spectra of organic molecules, J. Electron Spectrosc. Relat. Phenom., 1980, 21, 93. [all data]

Do and Raulin, 1992
Do, L.; Raulin, F., Gas chromatography of Titan's atmosphere. III. Analysis of low-molecular-weight hydrocarbons and nitriles with a CP-Sil-5 CB WCOT capillary column, J. Chromatogr., 1992, 591, 1-2, 297-301, https://doi.org/10.1016/0021-9673(92)80247-R . [all data]

Do and Raulin, 1989
Do, L.; Raulin, F., Gas chromatography of Titan's atmosphere. I. Analysis of low-molecular-weight hydrocarbons and nitriles with a PoraPLOT Q porous polymer coated open-tubular capillary column, J. Chromatogr., 1989, 481, 45-54, https://doi.org/10.1016/S0021-9673(01)96751-2 . [all data]


Notes

Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Gas Chromatography, References