2H-Pyran-2-ol, tetrahydro-
- Formula: C5H10O2
- Molecular weight: 102.1317
- IUPAC Standard InChI: InChI=1S/C5H10O2/c6-5-3-1-2-4-7-5/h5-6H,1-4H2
- IUPAC Standard InChIKey: CELWCAITJAEQNL-UHFFFAOYSA-N
- CAS Registry Number: 694-54-2
- Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript. - Other names: Tetrahydro-2-hydroxy-2H-pyran; Tetrahydro-2-pyranol; Tetrahydro-2H-pyran-2-ol; 2-Hydroxytetrahydropyran; 2-Tetrahydropyranol; δ-Valerolactol; Pyran-2-ol, tetrahydro-
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Gas phase ion energetics data
Go To: Top, 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
De-protonation reactions
C5H9O2- + =
By formula: C5H9O2- + H+ = C5H10O2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 1540. ± 13. | kJ/mol | D-EA | Baer, Brinkman, et al., 1991 | gas phase; Structure: cyclic H-bonded 5-hydroxypentanal enolate |
| ΔrH° | 1496. ± 8.8 | kJ/mol | G+TS | Baer, Brinkman, et al., 1991 | gas phase; For deprotonation of neutral acetal. |
| ΔrH° | 1502. ± 13. | kJ/mol | G+TS | Bartmess, Hays, et al., 1981 | gas phase; Between CF3CH2OH, MeSH for deprotonation, reprotonates at ca. HOAc due to isomerization. |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 1469. ± 8.4 | kJ/mol | IMRB | Baer, Brinkman, et al., 1991 | gas phase; For deprotonation of neutral acetal. |
| ΔrG° | 1452. ± 13. | kJ/mol | IMRB | Baer, Brinkman, et al., 1991 | gas phase; For reprotonation of anion: structure is cyclic H-bonded cyclic enolate |
| ΔrG° | 1474. ± 13. | kJ/mol | IMRB | Bartmess, Hays, et al., 1981 | gas phase; Between CF3CH2OH, MeSH for deprotonation, reprotonates at ca. HOAc due to isomerization. |
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.
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
Go To: Top, Gas phase ion energetics data, References
- Symbols used in this document:
ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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