2H-Pyran-2-ol, tetrahydro-
- Formula: C5H10O2
- Molecular weight: 102.1317
- 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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Reaction thermochemistry data
Go To: Top, Mass spectrum (electron ionization), References, Notes
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- + =
By formula: C5H9O2- + H+ = C5H10O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 368.0 ± 3.2 | kcal/mol | D-EA | Baer, Brinkman, et al., 1991 | gas phase; Structure: cyclic H-bonded 5-hydroxypentanal enolate; B |
ΔrH° | 357.6 ± 2.1 | kcal/mol | G+TS | Baer, Brinkman, et al., 1991 | gas phase; For deprotonation of neutral acetal.; B |
ΔrH° | 358.9 ± 3.1 | kcal/mol | G+TS | Bartmess, Hays, et al., 1981 | gas phase; Between CF3CH2OH, MeSH for deprotonation, reprotonates at ca. HOAc due to isomerization.; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 351.0 ± 2.0 | kcal/mol | IMRB | Baer, Brinkman, et al., 1991 | gas phase; For deprotonation of neutral acetal.; B |
ΔrG° | 347.0 ± 3.0 | kcal/mol | IMRB | Baer, Brinkman, et al., 1991 | gas phase; For reprotonation of anion: structure is cyclic H-bonded cyclic enolate; B |
ΔrG° | 352.3 ± 3.0 | kcal/mol | IMRB | Bartmess, Hays, et al., 1981 | gas phase; Between CF3CH2OH, MeSH for deprotonation, reprotonates at ca. HOAc due to isomerization.; B |
By formula: C5H10O2 = C5H10O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 5.4 | kcal/mol | Eqk | Shono, Godo, et al., 1971 | liquid phase; solvent: DMSO-d6; NMR; ALS |
Mass spectrum (electron ionization)
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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
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Additional Data
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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 |
References
Go To: Top, Reaction thermochemistry 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 ω-hydroxy aldehydes,
Bunseki Kagaku, 1971, 20, 1183-1186. [all data]
Notes
Go To: Top, Reaction thermochemistry data, Mass spectrum (electron ionization), 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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