tetrahydropyran-2-O anion


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
2.15 ± 0.11LPDBaer, Brinkman, et al., 1991Structure: cyclic H-bonded 5-hydroxypentanal enolate
2.60 ± 0.13D-EABaer, Brinkman, et al., 1991For deprotonation of neutral acetal.

Protonation reactions

C5H9O2- + Hydrogen cation = 2H-Pyran-2-ol, tetrahydro-

By formula: C5H9O2- + H+ = C5H10O2

Quantity Value Units Method Reference Comment
Δr368.0 ± 3.2kcal/molD-EABaer, Brinkman, et al., 1991gas phase; Structure: cyclic H-bonded 5-hydroxypentanal enolate
Δr357.6 ± 2.1kcal/molG+TSBaer, Brinkman, et al., 1991gas phase; For deprotonation of neutral acetal.
Δr358.9 ± 3.1kcal/molG+TSBartmess, Hays, et al., 1981gas phase; Between CF3CH2OH, MeSH for deprotonation, reprotonates at ca. HOAc due to isomerization.
Quantity Value Units Method Reference Comment
Δr351.0 ± 2.0kcal/molIMRBBaer, Brinkman, et al., 1991gas phase; For deprotonation of neutral acetal.
Δr347.0 ± 3.0kcal/molIMRBBaer, Brinkman, et al., 1991gas phase; For reprotonation of anion: structure is cyclic H-bonded cyclic enolate
Δr352.3 ± 3.0kcal/molIMRBBartmess, Hays, et al., 1981gas phase; Between CF3CH2OH, MeSH for deprotonation, reprotonates at ca. HOAc due to isomerization.

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.

Baer, Brinkman, et al., 1991
Baer, S.; Brinkman, E.A.; Brauman, J.I., Hemiacetal Anions: A Model for Tetrahedral Reaction Intermediates, J. Am. Chem. Soc., 1991, 113, 3, 805, https://doi.org/10.1021/ja00003a012 . [all data]

Bartmess, Hays, et al., 1981
Bartmess, J.E.; Hays, R.L.; Caldwell, G., The Addition of Carbanions to Carbonyl Groups in the Gas Phase, J. Am. Chem. Soc., 1981, 103, 6, 1338, https://doi.org/10.1021/ja00396a006 . [all data]


Notes

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