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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

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.

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

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

De-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.

Mass spectrum (electron ionization)

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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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Owner NIST Mass Spectrometry Data Center
Collection (C) 2014 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin CARL DJERASSI DEPT OF CHEM STANFORD UNIV STANFORD CALIF 94305
NIST MS number 46286

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References

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), 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]

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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