Propiolonitrile

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Phase change data

Go To: Top, Gas phase ion energetics data, Mass spectrum (electron ionization), 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: Robert L. Brown and Stephen E. Stein

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

Gas phase ion energetics data

Go To: Top, Phase change data, Mass spectrum (electron ionization), References, Notes

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)179.5kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity172.2kcal/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, 1986LBLHLM
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, 1986LBLHLM
CN+19.8 ± 0.2C2HEIDibeler, Reese, et al., 1961RDSH
C2+18.6 ± 0.2?EIDibeler, Reese, et al., 1961RDSH
C2H+18.84 ± 0.08CNEIHarland, 1986LBLHLM
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, 1986LBLHLM
C3H+18.0 ± 0.2NEIDibeler, Reese, et al., 1961RDSH
C3N+17.78 ± 0.08HEIHarland, 1986LBLHLM
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
Δr350.6 ± 2.1kcal/molG+TSTaft, Abboud, et al., 1988gas phase; B
Δr344.0 ± 3.5kcal/molEIAEGraupner, Merrigan, et al., 2006gas phase; B
Quantity Value Units Method Reference Comment
Δr342.9 ± 2.0kcal/molIMRETaft, Abboud, et al., 1988gas phase; B

Mass spectrum (electron ionization)

Go To: Top, Phase change data, Gas phase ion energetics data, 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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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

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References

Go To: Top, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), Notes

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

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]

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
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]

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]


Notes

Go To: Top, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), References