2-Propenenitrile

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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:
B - John E. Bartmess
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias

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Individual Reactions

C3H2N- + Hydrogen cation = 2-Propenenitrile

By formula: C3H2N- + H+ = C3H3N

Quantity Value Units Method Reference Comment
ΔrH°1553. ± 9.2kJ/molG+TSBartmess, 1980gas phase; value altered from reference due to change in acidity scale; B
ΔrH°1524. ± 19.kJ/molEIAEHeni and Illenberger, 1986gas phase; From CH2=CHCN. G3MP2B3 calculations indicate a dHacdi ca. 374 kcal/mol; B
Quantity Value Units Method Reference Comment
ΔrG°1528. ± 8.4kJ/molIMREBartmess, 1980gas phase; value altered from reference due to change in acidity scale; B

2-Propenenitrile + 1,3 Diphenylisobenzofuran = C23H17NO

By formula: C3H3N + C20H14O = C23H17NO

Quantity Value Units Method Reference Comment
ΔrH°-87.kJ/molKinSamuilov, Nurullina, et al., 1983liquid phase; solvent: Dichloroethane; Unpublished results; ALS
ΔrH°-87.4 ± 0.8kJ/molCmKiselev, Ustyugov, et al., 1977liquid phase; solvent: 1,2-Dichloroethane; ALS

(CAS Reg. No. 42117-12-4 • 42949672952-Propenenitrile) + 2-Propenenitrile = CAS Reg. No. 42117-12-4

By formula: (CAS Reg. No. 42117-12-4 • 4294967295C3H3N) + C3H3N = CAS Reg. No. 42117-12-4

Quantity Value Units Method Reference Comment
ΔrH°239. ± 9.2kJ/molN/ABartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B

C3H4N+ + 2-Propenenitrile = (C3H4N+ • 2-Propenenitrile)

By formula: C3H4N+ + C3H3N = (C3H4N+ • C3H3N)

Quantity Value Units Method Reference Comment
ΔrH°128.kJ/molPHPMSMeot-Ner (Mautner) and Sieck, 1991gas phase; M
Quantity Value Units Method Reference Comment
ΔrS°123.J/mol*KPHPMSMeot-Ner (Mautner) and Sieck, 1991gas phase; M

Propanenitrile, 3,3'-thiobis- + 2Ammonia = 22-Propenenitrile + ammonium sulphide

By formula: C6H8N2S + 2H3N = 2C3H3N + ammonium sulphide

Quantity Value Units Method Reference Comment
ΔrH°126.4 ± 2.5kJ/molCmGladstone and Chang, 1966liquid phase; Heat of formation derived by Cox and Pilcher, 1970; ALS

(CAS Reg. No. 180058-39-3 • 42949672952-Propenenitrile) + 2-Propenenitrile = CAS Reg. No. 180058-39-3

By formula: (CAS Reg. No. 180058-39-3 • 4294967295C3H3N) + C3H3N = CAS Reg. No. 180058-39-3

Quantity Value Units Method Reference Comment
ΔrH°95. ± 10.kJ/molN/ABartmess, 1980gas phase; B

22-Propenenitrile + ammonium sulphide = Propanenitrile, 3,3'-thiobis- + 2Ammonia

By formula: 2C3H3N + ammonium sulphide = C6H8N2S + 2H3N

Quantity Value Units Method Reference Comment
ΔrH°-126.4 ± 2.5kJ/molCmGladstone and Chang, 1966liquid phase; ALS

Gas phase ion energetics data

Go To: Top, Reaction thermochemistry data, Gas Chromatography, 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 C3H3N+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
IE (evaluated)10.91 ± 0.01eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)784.7kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity753.7kJ/molN/AHunter and Lias, 1998HL

Electron affinity determinations

EA (eV) Method Reference Comment
0.006505EFDSuess, Liu, et al., 2003Possibly dipole-stabilized anion; G3MP2B3 indicate valence anion is unbound by ca. 0.15 eV; B
0.006895EFDDesfrancois, Abdoul-Carime, et al., 1994EA: 6.9 meV. Dipole-bound state.; B

Ionization energy determinations

IE (eV) Method Reference Comment
10.91PEOhno, Matumoto, et al., 1984LBLHLM
10.91PEKimura, Katsumata, et al., 1981LLK
10.91PELake and Thompson, 1970RDSH
10.91 ± 0.01PIWatanabe, Nakayama, et al., 1962RDSH
11.1PEBieri, Asbrink, et al., 1982Vertical value; LBLHLM
10.92 ± 0.05PEHouk and Munchausen, 1976Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C2H2+13.13 ± 0.10HCNEIMomigny, Urbain, et al., 1965RDSH
C3HN+16.4 ± 0.1?EIChelobov, Dubov, et al., 1969RDSH
C3H2N+13.82 ± 0.08HEIMomigny, Urbain, et al., 1965RDSH
C3N+21.6 ± 0.1?EIChelobov, Dubov, et al., 1969RDSH

De-protonation reactions

C3H2N- + Hydrogen cation = 2-Propenenitrile

By formula: C3H2N- + H+ = C3H3N

Quantity Value Units Method Reference Comment
ΔrH°1553. ± 9.2kJ/molG+TSBartmess, 1980gas phase; value altered from reference due to change in acidity scale; B
ΔrH°1524. ± 19.kJ/molEIAEHeni and Illenberger, 1986gas phase; From CH2=CHCN. G3MP2B3 calculations indicate a dHacdi ca. 374 kcal/mol; B
Quantity Value Units Method Reference Comment
ΔrG°1528. ± 8.4kJ/molIMREBartmess, 1980gas phase; value altered from reference due to change in acidity scale; B

Gas Chromatography

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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

Kovats' RI, non-polar column, isothermal

View large format table.

Column type Active phase Temperature (C) I Reference Comment
CapillaryBPX-530.540.Aflalaye, Sternberg, et al., 199512. m/0.15 mm/0.25 μm, H2
CapillaryBPX-530.544.Aflalaye, Sternberg, et al., 199512. m/0.15 mm/0.25 μm, H2
CapillaryCP Sil 5 CB20.496.4Do and Raulin, 199225. m/0.15 mm/2. μm, H2
CapillaryPoraPLOT Q100.476.Do and Raulin, 198910. m/0.32 mm/10. μm, H2
CapillaryPoraPLOT Q160.482.Do and Raulin, 198910. m/0.32 mm/10. μm, H2
PackedSE-30100.500.Winskowski, 1983Gaschrom Q; Column length: 2. m

Van Den Dool and Kratz RI, non-polar column, temperature ramp

View large format table.

Column type Active phase I Reference Comment
CapillaryDB-5521.1Xu, van Stee, et al., 200330. m/0.25 mm/1. μm, He, 2.5 K/min; Tstart: 50. C; Tend: 200. C
PackedSE-30520.Fischer and Kusch, 1990Chromosorb W AW (80-100 mesh), 5. K/min; Column length: 1.5 m; Tstart: 60. C; Tend: 280. C

Normal alkane RI, non-polar column, isothermal

View large format table.

Column type Active phase Temperature (C) I Reference Comment
CapillaryOV-10132.516.Blazso, Ujszaszi, et al., 1980Column length: 20. m; Column diameter: 0.23 mm
PackedSynachrom150.482.Dufka, Malinsky, et al., 1971Helium, Synachrom (60-80 mesh); Column length: 1.5 m
PackedSynachrom150.488.Dufka, Malinsky, et al., 1971Helium, Synachrom (60-80 mesh); Column length: 1.5 m

Normal alkane RI, non-polar column, temperature ramp

View large format table.

Column type Active phase I Reference Comment
CapillaryPolydimethyl siloxane: CP-Sil 5 CB491.Bramston-Cook, 201360. m/0.25 mm/1.0 μm, Helium, 45. C @ 1.45 min, 3.6 K/min, 210. C @ 2.72 min
CapillaryOV-101495.Zenkevich, 200525. m/0.20 mm/0.10 μm, N2/He, 6. K/min; Tstart: 50. C; Tend: 250. C
CapillaryHP-5526.Jung, Wichmann, et al., 199925. m/0.20 mm/0.33 μm, 50. C @ 3. min, 5. K/min; Tend: 180. C

Normal alkane RI, non-polar column, custom temperature program

View large format table.

Column type Active phase I Reference Comment
CapillaryMethyl Silicone495.Zenkevich, 1999Program: not specified
CapillarySPB-1492.Flanagan, Streete, et al., 199760. m/0.53 mm/5. μm, He; Program: 40C(6min) => 5C/min => 80C => 10C/min => 200C
CapillaryPolydimethyl siloxanes495.Zenkevich, 1997Program: not specified
CapillarySPB-1492.Strete, Ruprah, et al., 199260. m/0.53 mm/5.0 μm, Helium; Program: 40 0C (6 min) 5 0C/min -> 80 0C 10 0C/min -> 200 0C
CapillarySPB-1490.Strete, Ruprah, et al., 199260. m/0.53 mm/5.0 μm, Helium; Program: not specified

Normal alkane RI, polar column, custom temperature program

View large format table.

Column type Active phase I Reference Comment
CapillaryCarbowax 400, Carbowax 20M, Carbowax 1540, Carbowax 4000, Superox 06, PEG 20M, etc.993.Waggott and Davies, 1984Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified
CapillaryCarbowax 20M1010.Ramsey and Flanagan, 1982Program: not specified

References

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Gas Chromatography, Notes

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

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]

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]

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]

Kiselev, Ustyugov, et al., 1977
Kiselev, V.D.; Ustyugov, A.N.; Breus, I.P.; Konovalov, A.I., Kinetic and thermochemical study of the Diels-Alder reaction, Dokl. Phys. Chem. (Engl. Transl.), 1977, 234, 320-322, In original 1089. [all data]

Bartmess, Scott, et al., 1979
Bartmess, J.E.; Scott, J.A.; McIver, R.T., Jr., The gas phase acidity scale from methanol to phenol, J. Am. Chem. Soc., 1979, 101, 6047. [all data]

Meot-Ner (Mautner) and Sieck, 1991
Meot-Ner (Mautner), M.; Sieck, L.W., Proton affinity ladders from variable-temperature equilibrium measurements. 1. A reevaluation of the upper proton affinity range, J. Am. Chem. Soc., 1991, 113, 12, 4448, https://doi.org/10.1021/ja00012a012 . [all data]

Gladstone and Chang, 1966
Gladstone, S.; Chang, H.Y., Determination of the standard heat of formation of 3,3'-thiodipropionitrile, J. Chem. Eng. Data, 1966, 11, 238-239. [all data]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [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]

Suess, Liu, et al., 2003
Suess, L.; Liu, Y.; Parthasarathy, R.; Dunning, F.B., Dipole-bound negative ions: Collisional destruction and blackbody-radiation-induced photodetachment, J. Chem. Phys., 2003, 119, 24, 12890-12894, https://doi.org/10.1063/1.1628215 . [all data]

Desfrancois, Abdoul-Carime, et al., 1994
Desfrancois, C.; Abdoul-Carime, H.; Khelifa, N.; Schermann, J.P., Fork 1/r to 1/r2 Potentials: Electron Exchange between Rydberg Atoms and Polar Molecules, Phys. Rev. Lett., 1994, 73, 18, 2436, https://doi.org/10.1103/PhysRevLett.73.2436 . [all data]

Ohno, Matumoto, et al., 1984
Ohno, K.; Matumoto, S.; Imai, K.; Haraa, Y., Penning ionization electron spectroscopy of nitriles, J. Phys. Chem., 1984, 88, 206. [all data]

Kimura, Katsumata, et al., 1981
Kimura, K.; Katsumata, S.; Achiba, Y.; Yamazaki, T.; Iwata, S., Ionization energies, Ab initio assignments, and valence electronic structure for 200 molecules in Handbook of HeI Photoelectron Spectra of Fundamental Organic Compounds, Japan Scientific Soc. Press, Tokyo, 1981. [all data]

Lake and Thompson, 1970
Lake, R.F.; Thompson, H., The photoelectron spectra of some molecules containing the C N group, Proc. Roy. Soc. (London), 1970, A317, 187. [all data]

Watanabe, Nakayama, et al., 1962
Watanabe, K.; Nakayama, T.; Mottl, J., Ionization potentials of some molecules, J. Quant. Spectry. Radiative Transfer, 1962, 2, 369. [all data]

Bieri, Asbrink, et al., 1982
Bieri, G.; Asbrink, L.; Von Niessen, W., 30.4-nm He(II) photoelectron spectra of organic molecules, J. Electron Spectrosc. Relat. Phenom., 1982, 27, 129. [all data]

Houk and Munchausen, 1976
Houk, K.N.; Munchausen, L.L., Ionization potentials, electron affinities, reactivities of cyanoalkenes related electron-deficient alkenes. A frontier molecular orbital treatment of cyanoalkene reactivities in cycloaddition, electrophilic, nucleophilic, and radical reactions., J. Am. Chem. Soc., 1976, 98, 937. [all data]

Momigny, Urbain, et al., 1965
Momigny, J.; Urbain, J.; Wankenne, H., Les effets de l'impact electronique sur la pyridine et les diazines isomeres, Bull. Soc. Roy. Sci. Liege, 1965, 34, 337. [all data]

Chelobov, Dubov, et al., 1969
Chelobov, F.N.; Dubov, S.S.; Tikhomirov, M.V.; Dobrovitskii, M.I.; Gitel', P.O.; Rozenshtein, S.M., Processes in fluoroacrylonitriles under electron impact, Zh. Fiz. Khim., 1969, 43, 33, In original 15. [all data]

Aflalaye, Sternberg, et al., 1995
Aflalaye, A.; Sternberg, R.; Raulin, F.; Vidal-Madjar, C., Gas chromatography of Titan's atmosphere. VI. Analysis of low-molecular-mass hydrocarbons and nitriles with BPX5 capillary columns, J. Chromatogr. A, 1995, 708, 2, 283-291, https://doi.org/10.1016/0021-9673(95)00410-O . [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]

Winskowski, 1983
Winskowski, J., Gaschromatographische Identifizierung von Stoffen anhand von Indexziffem und unterschiedlichen Detektoren, Chromatographia, 1983, 17, 3, 160-165, https://doi.org/10.1007/BF02271041 . [all data]

Xu, van Stee, et al., 2003
Xu, X.; van Stee, L.L.P.; Williams, J.; Beens, J.; Adahchour, M.; Vreuls, R.J.J.; Brinkman, U.A.Th.; Lelieveld, J., Comprehensive two-dimensional gas chromatography (GC×GC) measurements of volatile organic compounds in the atmosphere, Atmos. Chem. Phys., 2003, 3, 3, 665-682, https://doi.org/10.5194/acp-3-665-2003 . [all data]

Fischer and Kusch, 1990
Fischer, W.G.; Kusch, P., Automatic sampler for Curie-point pyrolysis-gas chromatography with on-column introduction of pyrolysates, J. Chromatogr., 1990, 518, 9-19, https://doi.org/10.1016/S0021-9673(01)93158-9 . [all data]

Blazso, Ujszaszi, et al., 1980
Blazso, M.; Ujszaszi, K.; Jakab, E., Isomeric structure of styrene-acrylonitrile and styrene-methylacrylate copolymer pyrolysis products, Chromatographia, 1980, 13, 3, 151-156, https://doi.org/10.1007/BF02259304 . [all data]

Dufka, Malinsky, et al., 1971
Dufka, O.; Malinsky, J.; Vladyka, J., Sorpcni materialy pro plynovou chromatographii - III, Chemicky promysl., 1971, 21/46, 9, 459-463. [all data]

Bramston-Cook, 2013
Bramston-Cook, R., Kovats indices for C2-C13 hydrocarbons and selected oxygenated/halocarbons with 100 % dimethylpolysiloxane columns, 2013, retrieved from http://lotusinstruments.com/monographs/List .... [all data]

Zenkevich, 2005
Zenkevich, I.G., Experimentally measured retention indices., 2005. [all data]

Jung, Wichmann, et al., 1999
Jung, A.; Wichmann, K.-H.; Kolb, M., VOC emission of polymeric packaging materials, LaborPraxis, 1999, 23, 9, 20-22. [all data]

Zenkevich, 1999
Zenkevich, I.G., New Application of the Retention Index Concept in Gas and High Performance Liquid Chromatography, Fresenius' J. Anal. Chem., 1999, 365, 4, 305-309, https://doi.org/10.1007/s002160051491 . [all data]

Flanagan, Streete, et al., 1997
Flanagan, R.J.; Streete, P.J.; Ramsey, J.D., Volatile Substance Abuse, UNODC Technical Series, No 5, United Nations, Office on Drugs and Crime, Vienna International Centre, PO Box 500, A-1400 Vienna, Austria, 1997, 56, retrieved from http://www.odccp.org/pdf/technicalseries1997-01-011.pdf. [all data]

Zenkevich, 1997
Zenkevich, I.G., Influence of the Variations of Dynamics Molecular Parameterts on the Additivity of Chromatigraphic Retention Indices of Products of Organic Reactions Relative to Initial Reagents, Dokl. Akad. Nauk (Rus.), 1997, 353, 5, 625-627. [all data]

Strete, Ruprah, et al., 1992
Strete, P.J.; Ruprah, M.; Ramsey, J.D.; Flanagan, R.J., Detection and identification of volatile substances by headspace capillary gas chromatography to aid the diagnosis of acute poisoning, Analyst, 1992, 117, 7, 1111-1127, https://doi.org/10.1039/an9921701111 . [all data]

Waggott and Davies, 1984
Waggott, A.; Davies, I.W., Identification of organic pollutants using linear temperature programmed retention indices (LTPRIs) - Part II, 1984, retrieved from http://dwi.defra.gov.uk/research/completed-research/reports/dwi0383.pdf. [all data]

Ramsey and Flanagan, 1982
Ramsey, J.D.; Flanagan, R.J., Detection and Identification of Volatile Organic Compounds in Blood by Headspace Gas Chromatography as an Aid to the Diagnosis of Solvent Abuse, J. Chromatogr., 1982, 240, 2, 423-444, https://doi.org/10.1016/S0021-9673(00)99622-5 . [all data]

Notes

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