CH2=CHCHCN anion
- Formula: C4H4N-
- Molecular weight: 66.0818
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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 ± 0.30 | D-EA | Luna, Mo, et al., 2006 | Acid CH3CH=CHCN. Between MeSH, EtSH |
| 1.35 ± 0.28 | D-EA | Dahlke and Kass, 1991 | Between MeCHO, HCONH2. Reprotonation site uncertain. |
Protonation reactions
C4H4N- + =
By formula: C4H4N- + H+ = C4H5N
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 357.3 ± 3.0 | kcal/mol | G+TS | Luna, Mo, et al., 2006 | gas phase; Acid CH3CH=CHCN. Between MeSH, EtSH |
| ΔrH° | 358.8 ± 3.1 | kcal/mol | G+TS | Chou, Dahlke, et al., 1993 | gas phase; Acid: CH2=CHCH2CN |
| ΔrH° | 363.5 ± 5.1 | kcal/mol | G+TS | Dahlke and Kass, 1991 | gas phase; Between MeCHO, HCONH2. Reprotonation site uncertain. |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 349.9 ± 3.0 | kcal/mol | IMRB | Luna, Mo, et al., 2006 | gas phase; Acid CH3CH=CHCN. Between MeSH, EtSH |
| ΔrG° | 351.7 ± 3.0 | kcal/mol | IMRB | Chou, Dahlke, et al., 1993 | gas phase; Acid: CH2=CHCH2CN |
| ΔrG° | 356.3 ± 5.0 | kcal/mol | IMRB | Dahlke and Kass, 1991 | gas phase; Between MeCHO, HCONH2. Reprotonation site uncertain. |
| ΔrG° | <365.0 ± 2.0 | kcal/mol | IMRB | Dawson and Nibbering, 1980 | gas phase; Acid: CH2=CHCH2CN |
References
Go To: Top, 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]
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
Go To: Top, Gas phase ion energetics data, References
- Symbols used in this document:
EAneutral Electron affinity of neutral species ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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