CH2=CHCHCN anion


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 compiled by: John E. Bartmess

Electron affinity of neutral species

EAneutral (eV) Method Reference Comment
1.62 ± 0.30D-EALuna, Mo, et al., 2006Acid CH3CH=CHCN. Between MeSH, EtSH
1.35 ± 0.28D-EADahlke and Kass, 1991Between MeCHO, HCONH2. Reprotonation site uncertain.

Protonation reactions

C4H4N- + Hydrogen cation = 3-Butenenitrile

By formula: C4H4N- + H+ = C4H5N

Quantity Value Units Method Reference Comment
Δr357.3 ± 3.0kcal/molG+TSLuna, Mo, et al., 2006gas phase; Acid CH3CH=CHCN. Between MeSH, EtSH
Δr358.8 ± 3.1kcal/molG+TSChou, Dahlke, et al., 1993gas phase; Acid: CH2=CHCH2CN
Δr363.5 ± 5.1kcal/molG+TSDahlke and Kass, 1991gas phase; Between MeCHO, HCONH2. Reprotonation site uncertain.
Quantity Value Units Method Reference Comment
Δr349.9 ± 3.0kcal/molIMRBLuna, Mo, et al., 2006gas phase; Acid CH3CH=CHCN. Between MeSH, EtSH
Δr351.7 ± 3.0kcal/molIMRBChou, Dahlke, et al., 1993gas phase; Acid: CH2=CHCH2CN
Δr356.3 ± 5.0kcal/molIMRBDahlke and Kass, 1991gas phase; Between MeCHO, HCONH2. Reprotonation site uncertain.
Δr<365.0 ± 2.0kcal/molIMRBDawson and Nibbering, 1980gas phase; Acid: CH2=CHCH2CN

References

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

Luna, Mo, et al., 2006
Luna, A.; Mo, O.; Yanez, M.; Gal, J.F.; Maria, P.C.; Guillemin, J.C., Gas-phase protonation and deprotonation of acrylonitrile derivatives N equivalent to C-CH=CH-X (X=CH3, NH2, PH2, SiH3), Chem. Eur. J., 2006, 12, 36, 9254-9261, https://doi.org/10.1002/chem.200600154 . [all data]

Dahlke and Kass, 1991
Dahlke, G.D.; Kass, S.R., Substituent Effects in the Gas Phase - 1-Substituted Allyl Anions, J. Am. Chem. Soc., 1991, 113, 15, 5566, https://doi.org/10.1021/ja00015a008 . [all data]

Chou, Dahlke, et al., 1993
Chou, P.K.; Dahlke, G.D.; Kass, S.R., Unimolecular Rearrangements of Carbanions in the Gas Phase .2. Cyclopropyl Anions, J. Chem. Soc. Chem. Comm., 1993, 115, 1, 315, https://doi.org/10.1021/ja00054a045 . [all data]

Dawson and Nibbering, 1980
Dawson, J.H.J.; Nibbering, N.M.M., The gas phase anionic chemistry of saturated and unsaturated aliphatic nitriles, Int. J. Mass Spectrom. Ion Phys., 1980, 33, 3. [all data]


Notes

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