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tetrahydropyran-2-O anion


Reaction thermochemistry 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

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Individual Reactions

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

By formula: C5H9O2- + H+ = C5H10O2

Quantity Value Units Method Reference Comment
Deltar1540. ± 13.kJ/molD-EABaer, Brinkman, et al., 1991gas phase; Structure: cyclic H-bonded 5-hydroxypentanal enolate
Deltar1496. ± 8.8kJ/molG+TSBaer, Brinkman, et al., 1991gas phase; For deprotonation of neutral acetal.
Deltar1502. ± 13.kJ/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
Deltar1469. ± 8.4kJ/molIMRBBaer, Brinkman, et al., 1991gas phase; For deprotonation of neutral acetal.
Deltar1452. ± 13.kJ/molIMRBBaer, Brinkman, et al., 1991gas phase; For reprotonation of anion: structure is cyclic H-bonded cyclic enolate
Deltar1474. ± 13.kJ/molIMRBBartmess, Hays, et al., 1981gas phase; Between CF3CH2OH, MeSH for deprotonation, reprotonates at ca. HOAc due to isomerization.

Gas phase ion energetics data

Go To: Top, Reaction thermochemistry data, References, Notes

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
Deltar1540. ± 13.kJ/molD-EABaer, Brinkman, et al., 1991gas phase; Structure: cyclic H-bonded 5-hydroxypentanal enolate
Deltar1496. ± 8.8kJ/molG+TSBaer, Brinkman, et al., 1991gas phase; For deprotonation of neutral acetal.
Deltar1502. ± 13.kJ/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
Deltar1469. ± 8.4kJ/molIMRBBaer, Brinkman, et al., 1991gas phase; For deprotonation of neutral acetal.
Deltar1452. ± 13.kJ/molIMRBBaer, Brinkman, et al., 1991gas phase; For reprotonation of anion: structure is cyclic H-bonded cyclic enolate
Deltar1474. ± 13.kJ/molIMRBBartmess, Hays, et al., 1981gas phase; Between CF3CH2OH, MeSH for deprotonation, reprotonates at ca. HOAc due to isomerization.

References

Go To: Top, Reaction thermochemistry data, 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.

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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