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3-Butenenitrile

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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 evaluated as indicated in comments:
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

Quantity Value Units Method Reference Comment
IE (evaluated)10.20 ± 0.02eVN/AN/AL

Ionization energy determinations

IE (eV) Method Reference Comment
10.22PEWillett and Baer, 1980LLK
10.18PELake and Thompson, 1970RDSH
10.39 ± 0.01PIWatanabe, Nakayama, et al., 1962RDSH
10.55PEOhno, Matumoto, et al., 1984Vertical value; LBLHLM

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
CH2N+11.90?PIWillett and Baer, 1980LLK
C2H3+12.90?PIWillett and Baer, 1980LLK
C2H3N+11.10C2H2EISakurai and Jennings, 1981LLK
C2H3N+11.10?PIWillett and Baer, 1980LLK
C3H2N+12.05?PIWillett and Baer, 1980LLK
C3H3+12.10?PIWillett and Baer, 1980LLK
C3H4+11.50?PIWillett and Baer, 1980LLK
C4H4N+12.30HPIWillett and Baer, 1980LLK

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

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.

Willett and Baer, 1980
Willett, G.D.; Baer, T., Thermochemistry and dissociation dynamics of state-selected C4H4X ions. 3. C4H5N+, J. Am. Chem. Soc., 1980, 102, 6774. [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]

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]

Sakurai and Jennings, 1981
Sakurai, H.; Jennings, K.R., A study of the structures of decomposing and non-decomposing [C4H5N]+ ions formed from different neutral species, Org. Mass Spectrom., 1981, 16, 393. [all data]

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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