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
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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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Information on this page:
Other data available:
- Gas phase ion energetics data
- Mass spectrum (electron ionization)
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Reaction thermochemistry data

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^- + = 2H-Pyran-2-ol, tetrahydro-

By formula: C₅H₉O₂^- + H⁺ = C₅H₁₀O₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	368.0 ± 3.2	kcal/mol	D-EA	Baer, Brinkman, et al., 1991	gas phase; Structure: cyclic H-bonded 5-hydroxypentanal enolate; B
Δ_rH°	357.6 ± 2.1	kcal/mol	G+TS	Baer, Brinkman, et al., 1991	gas phase; For deprotonation of neutral acetal.; B
Δ_rH°	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
Δ_rG°	351.0 ± 2.0	kcal/mol	IMRB	Baer, Brinkman, et al., 1991	gas phase; For deprotonation of neutral acetal.; B
Δ_rG°	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
Δ_rG°	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

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

By formula: C₅H₁₀O₂ = C₅H₁₀O₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	5.4	kcal/mol	Eqk	Shono, Godo, et al., 1971	liquid phase; solvent: DMSO-d6; NMR; ALS

References

Go To: Top, Reaction thermochemistry data, Notes

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, References

Symbols used in this document:

Δ_rG° Free energy of reaction at standard conditions

Δ_rH° Enthalpy of reaction at standard conditions
Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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Δ_rG°	Free energy of reaction at standard conditions
Δ_rH°	Enthalpy of reaction at standard conditions