Piperidine, 2,2,6,6-tetramethyl-

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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:
HL - Edward P. Hunter and 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

Quantity Value Units Method Reference Comment
Proton affinity (review)987.0kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity953.9kJ/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
7.59 ± 0.05PERozeboom and Houk, 1982LBLHLM
7.39PEBodor, Kaminski, et al., 1974LLK
8.14PEAue and Bowers, 1979Vertical value; LLK

De-protonation reactions

C9H18N- + Hydrogen cation = Piperidine, 2,2,6,6-tetramethyl-

By formula: C9H18N- + H+ = C9H19N

Quantity Value Units Method Reference Comment
Δr1630.5 ± 3.0kJ/molG+TSGrimm and Bartmess, 1992gas phase; B
Quantity Value Units Method Reference Comment
Δr1599.5 ± 1.7kJ/molIMREGrimm and Bartmess, 1992gas phase; B

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.

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]

Rozeboom and Houk, 1982
Rozeboom, M.D.; Houk, K.N., Stereospecific alkyl group effects on amine lone-pair ionization potentials: Photoelectron spectra of alkylpiperidines, J. Am. Chem. Soc., 1982, 104, 1189. [all data]

Bodor, Kaminski, et al., 1974
Bodor, N.; Kaminski, J.J.; Worley, S.D.; Colton, R.J.; Lee, T.H.; Rabalais, J.W., Photoelectron spectra, hydrolytic stability, and antimicrobial activity of N-chlorinated piperidines, J. Pharm. Sci., 1974, 63, 1387. [all data]

Aue and Bowers, 1979
Aue, D.H.; Bowers, M.T., Chapter 9. Stabilities of positive ions from equilibrium gas phase basicity measurements in Ions Chemistry,, ed. M.T. Bowers, 1979. [all data]

Grimm and Bartmess, 1992
Grimm, D.T.; Bartmess, J.E., The Intrinsic (Gas Phase) Basicity of some Anions Commonly Used in Condensed-Phase Synthesis, J. Am. Chem. Soc., 1992, 114, 4, 1227, https://doi.org/10.1021/ja00030a016 . [all data]


Notes

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