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Piperidine

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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
L - Sharon G. Lias

Data compiled as indicated in comments:
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)8.03 ± 0.11eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)228.0kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity220.kcal/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
8.20 ± 0.05PERozeboom and Houk, 1982LBLHLM
8.05 ± 0.05PEPesterev, Gabdrakipov, et al., 1979LLK
7.8PEAue and Bowers, 1979LLK
7.9 ± 0.1PEAue, Webb, et al., 1976LLK
8.7EIKiser and Gallegos, 1962RDSH
9.15CTSCollin, 1960RDSH
8.65 ± 0.10PEGan and Peel, 1979Vertical value; LLK
8.67PEDaamen and Oskam, 1978Vertical value; LLK
8.64 ± 0.05PEMorishima, Yoshikawa, et al., 1975Vertical value; LLK
8.66 ± 0.03PEColonna, Distefano, et al., 1975Vertical value; LLK
8.660PEAue, Webb, et al., 1975Vertical value; LLK
8.64 ± 0.02PEYoshikawa, Hashimoto, et al., 1974Vertical value; LLK

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.

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]

Pesterev, Gabdrakipov, et al., 1979
Pesterev, V.I.; Gabdrakipov, V.Z.; Artyukhin, V.I.; Agashkin, O.V., The ionisation and excitation of the conformers of piperidine and its alkyl derivatives, Russ. J. Phys. Chem., 1979, 53, 845. [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]

Aue, Webb, et al., 1976
Aue, D.H.; Webb, H.M.; Bowers, M.T., Quantitative proton affinities, ionization potentials, and hydrogen affinities of alkylamines, J. Am. Chem. Soc., 1976, 98, 311. [all data]

Kiser and Gallegos, 1962
Kiser, R.W.; Gallegos, E.J., A technique for the rapid determination of ionization and appearance potentials, J. Phys. Chem., 1962, 66, 947. [all data]

Collin, 1960
Collin, J.E., Relations between charge-transfer spectra and ionization potentials of some electron-donor organic molecules, Z. Elektrochem., 1960, 64, 936. [all data]

Gan and Peel, 1979
Gan, T.-H.; Peel, J.B., Photoelectron spectroscopic studies of piperidine and its N-halo derivatives, Aust. J. Chem., 1979, 32, 475. [all data]

Daamen and Oskam, 1978
Daamen, H.; Oskam, A., Bonding properties of some monosubstituted chromium and tungsten hexacarbonyls M(CO)5L (L=amine, substituted pyridine, azine), Inorg. Chim. Acta, 1978, 26, 81. [all data]

Morishima, Yoshikawa, et al., 1975
Morishima, I.; Yoshikawa, K.; Hashimoto, M.; Bekki, K., Homoallylic interaction between the nitrogen lone pair and the nonadjacent «pi» bond in cyclic and bicyclic amines. I. Photoelectron spectroscopic study, J. Am. Chem. Soc., 1975, 97, 4283. [all data]

Colonna, Distefano, et al., 1975
Colonna, F.P.; Distefano, G.; Pignataro, S.; Pitacco, G.; Valentin, E., Ionization energies of some amines and enamines and an estimation of their relative basicity in gaseous phase, J. Chem. Soc. Faraday Trans. 2, 1975, 71, 1572. [all data]

Aue, Webb, et al., 1975
Aue, D.H.; Webb, H.M.; Bowers, M.T., Proton affinities, ionization potentials, and hydrogen affinities of nitrogen and oxygen bases. Hybridization effects, J. Am. Chem. Soc., 1975, 97, 4137. [all data]

Yoshikawa, Hashimoto, et al., 1974
Yoshikawa, K.; Hashimoto, M.; Morishima, I., Photoelectron spectroscopic study of cyclic amines. The relation between ionization potentials, basicities, and s character of the nitrogen lone pair electrons, J. Am. Chem. Soc., 1974, 96, 288. [all data]


Notes

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