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2H-Pyran-2-ol, tetrahydro-


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 as indicated in comments:
B - John E. Bartmess
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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

2H-Pyran-2-ol, tetrahydro- = 5-hydroxyvaleraldehyde

By formula: C5H10O2 = C5H10O2

Quantity Value Units Method Reference Comment
Deltar23.kJ/molEqkShono, Godo, et al., 1971liquid phase; solvent: DMSO-d6; NMR; ALS

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]

Shono, Godo, et al., 1971
Shono, T.; Godo, M.; Shinra, K., High resolution NMR studies of ring-chain tautomerism in «omega»-hydroxy aldehydes, Bunseki Kagaku, 1971, 20, 1183-1186. [all data]


Notes

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