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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
Deltafgas354.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+ 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

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
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

Ion clustering data

Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, 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: Michael M. Meot-Ner (Mautner) and Sharon G. Lias

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. Searches may be limited to ion clustering reactions. A general reaction search form is also available.

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

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+

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
Quantity Value Units Method Reference Comment
Deltar108.J/mol*KPHPMSSpeller and Meot-Ner (Mautner), 1985gas phase

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

IR Spectrum

Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, 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

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 .


Mass spectrum (electron ionization)

Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Gas Chromatography, NIST Free Links, 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

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 NIST Mass Spectrometry Data Center, 1990.
NIST MS number 118857

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


Gas Chromatography

Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), NIST Free Links, 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. «mu»m, H2
CapillaryPoraPLOT Q100.421.Do and Raulin, 198910. m/0.32 mm/10. «mu»m, H2
CapillaryPoraPLOT Q160.424.Do and Raulin, 198910. m/0.32 mm/10. «mu»m, H2

References

Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, 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, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, References