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CH2=CHCHCN anion


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 by: John E. Bartmess

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Individual Reactions

C4H4N- + Hydrogen cation = 3-Butenenitrile

By formula: C4H4N- + H+ = C4H5N

Quantity Value Units Method Reference Comment
Deltar1495. ± 13.kJ/molG+TSLuna, Mo, et al., 2006gas phase; Acid CH3CH=CHCN. Between MeSH, EtSH
Deltar1501. ± 13.kJ/molG+TSChou, Dahlke, et al., 1993gas phase; Acid: CH2=CHCH2CN
Deltar1521. ± 21.kJ/molG+TSDahlke and Kass, 1991gas phase; Between MeCHO, HCONH2. Reprotonation site uncertain.
Quantity Value Units Method Reference Comment
Deltar1464. ± 13.kJ/molIMRBLuna, Mo, et al., 2006gas phase; Acid CH3CH=CHCN. Between MeSH, EtSH
Deltar1472. ± 13.kJ/molIMRBChou, Dahlke, et al., 1993gas phase; Acid: CH2=CHCH2CN
Deltar1491. ± 21.kJ/molIMRBDahlke and Kass, 1991gas phase; Between MeCHO, HCONH2. Reprotonation site uncertain.
Deltar<1527. ± 8.4kJ/molIMRBDawson and Nibbering, 1980gas phase; Acid: CH2=CHCH2CN

Gas phase ion energetics data

Go To: Top, Reaction thermochemistry 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: 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
Deltar1495. ± 13.kJ/molG+TSLuna, Mo, et al., 2006gas phase; Acid CH3CH=CHCN. Between MeSH, EtSH
Deltar1501. ± 13.kJ/molG+TSChou, Dahlke, et al., 1993gas phase; Acid: CH2=CHCH2CN
Deltar1521. ± 21.kJ/molG+TSDahlke and Kass, 1991gas phase; Between MeCHO, HCONH2. Reprotonation site uncertain.
Quantity Value Units Method Reference Comment
Deltar1464. ± 13.kJ/molIMRBLuna, Mo, et al., 2006gas phase; Acid CH3CH=CHCN. Between MeSH, EtSH
Deltar1472. ± 13.kJ/molIMRBChou, Dahlke, et al., 1993gas phase; Acid: CH2=CHCH2CN
Deltar1491. ± 21.kJ/molIMRBDahlke and Kass, 1991gas phase; Between MeCHO, HCONH2. Reprotonation site uncertain.
Deltar<1527. ± 8.4kJ/molIMRBDawson and Nibbering, 1980gas phase; Acid: CH2=CHCH2CN

References

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

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]

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]

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]

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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