Tetrahydropyran
- Formula: C5H10O
- Molecular weight: 86.1323
- IUPAC Standard InChIKey: DHXVGJBLRPWPCS-UHFFFAOYSA-N
- CAS Registry Number: 142-68-7
- 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: Oxacyclohexane; Oxane; 2H-Pyran, tetrahydro-; Pentamethylene oxide; Tetrahydro-2H-pyran; THP
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Gas phase thermochemistry data
Go To: Top, Gas phase ion energetics data, Gas Chromatography, 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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -223.8 ± 1.0 | kJ/mol | Cm | Pell and Pilcher, 1965 | ALS |
ΔfH°gas | -220. ± 3. | kJ/mol | Ccb | Snelson and Skinner, 1961 | ALS |
ΔfH°gas | -223.4 ± 1.5 | kJ/mol | Ccb | Cass, Fletcher, et al., 1958 | Reanalyzed by Cox and Pilcher, 1970, Original value = -212. kJ/mol; ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°gas | -3173.3 ± 0.96 | kJ/mol | Cm | Pell and Pilcher, 1965 | Corresponding ΔfHºgas = -223.4 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
Constant pressure heat capacity of gas
Cp,gas (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
33.90 | 50. | Dorofeeva O.V., 1992 | p=1 bar. Selected values are in close agreement with those calculated by [ Vedal D., 1975].; GT |
41.62 | 100. | ||
53.05 | 150. | ||
66.28 | 200. | ||
90.06 | 273.15 | ||
99.1 ± 3.0 | 298.15 | ||
99.82 | 300. | ||
137.09 | 400. | ||
171.01 | 500. | ||
199.70 | 600. | ||
223.66 | 700. | ||
243.80 | 800. | ||
260.83 | 900. | ||
275.32 | 1000. | ||
287.68 | 1100. | ||
298.26 | 1200. | ||
307.34 | 1300. | ||
315.16 | 1400. | ||
321.92 | 1500. |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Gas Chromatography, References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
L - Sharon G. Lias
Data compiled as indicated in comments:
MM - Michael M. Meot-Ner (Mautner)
LL - Sharon G. Lias and Joel F. Liebman
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
View reactions leading to C5H10O+ (ion structure unspecified)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 9.25 ± 0.01 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 822.8 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 795.4 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Gas basicity at 298K
Gas basicity (review) (kJ/mol) | Reference | Comment |
---|---|---|
799.1 ± 0.1 | Decouzon, Gal, et al., 1996 | T = 338K; MM |
799.2 | Decouzon, Gal, et al., 1996 | T = T(eff) = 430K; MM |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.24 ± 0.05 | EI | Holmes and Lossing, 1991 | LL |
9.16 | PE | Behan, Dean, et al., 1976 | LLK |
9.25 ± 0.01 | S | Hernandez, 1963 | RDSH |
9.26 ± 0.03 | PI | Watanabe, Nakayama, et al., 1962 | RDSH |
9.57 | PE | Kimura, Katsumata, et al., 1981 | Vertical value; LLK |
9.46 | PE | Planckaert, Doucet, et al., 1974 | Vertical value; LLK |
9.48 | PE | Kobayashi and Nagakura, 1973 | Vertical value; LLK |
9.50 | PE | Sweigart and Turner, 1972 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C2H4+ | ~13.8 | ? | EI | Collin and Conde-Caprace, 1966 | RDSH |
C2H5O+ | 11.56 | ? | EI | Collin and Conde-Caprace, 1966 | RDSH |
C3H5+ | ~12.8 | ? | EI | Collin and Conde-Caprace, 1966 | RDSH |
C4H7+ | ~12.2 | CH2O+H | EI | Collin and Conde-Caprace, 1966 | RDSH |
C4H8+ | 11.88 | CH2O? | EI | Collin and Conde-Caprace, 1966 | RDSH |
C5H9O+ | 11.22 | H | EI | Collin and Conde-Caprace, 1966 | RDSH |
Gas Chromatography
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics 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
Kovats' RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Packed | Apiezon L | 120. | 709. | Bogoslovsky, Anvaer, et al., 1978 | Celite 545 |
Packed | Apiezon L | 160. | 729. | Bogoslovsky, Anvaer, et al., 1978 | Celite 545 |
Packed | Apiezon L | 130. | 714. | Bogoslovsky, Anvaer, et al., 1978 | |
Packed | Apiezon L | 170. | 720. | Jonas, Janák, et al., 1966 | H2 |
Packed | Apiezon L | 170. | 740. | Jonas, Janák, et al., 1966 | H2 |
Packed | Apiezon L | 170. | 740. | Jonas, Kratochvíl, et al., 1966 | Column length: 2. m |
Packed | Apiezon L | 130. | 714. | Wehrli and Kováts, 1959 | Celite; Column length: 2.25 m |
Packed | Apiezon L | 70. | 697. | Wehrli and Kováts, 1959 | Celite; Column length: 2.25 m |
Kovats' RI, polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Packed | PEG-2000 | 150. | 972. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
Packed | PEG-2000 | 152. | 988. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
Packed | PEG-2000 | 179. | 1010. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
Packed | PEG-2000 | 180. | 969. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
Packed | PEG-2000 | 200. | 965. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
Normal alkane RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Packed | Apieson L | 120. | 736. | Kurdina, Markovich, et al., 1969 | not specified, not specified |
Packed | Apieson L | 120. | 714. | Kurdina, Markovich, et al., 1969 | not specified, not specified |
Packed | Apieson L | 120. | 714. | Kurdina, Markovich, et al., 1969 | not specified, not specified |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Methyl Silicone | 689. | Farkas, Héberger, et al., 2004 | Program: not specified |
Capillary | SE-30 | 690. | Vinogradov, 2004 | Program: not specified |
Capillary | Methyl Silicone | 689. | Zenkevich, 1998 | Program: not specified |
Normal alkane RI, polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Carbowax 20M | 930. | Vinogradov, 2004 | Program: not specified |
Capillary | Carbowax 400, Carbowax 20M, Carbowax 1540, Carbowax 4000, Superox 06, PEG 20M, etc. | 930. | Waggott and Davies, 1984 | Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified |
References
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Pell and Pilcher, 1965
Pell, A.S.; Pilcher, G.,
Measurements of heats of combustion by flame calorimetry. Part 3.-Ethylene oxide, trimethylene oxide, tetrahydrofuran and tetrahydropy,
Trans. Faraday Soc., 1965, 61, 71-77. [all data]
Snelson and Skinner, 1961
Snelson, A.; Skinner, H.A.,
Heats of combustion: sec-propanol, 1,4-dioxan, 1,3-dioxan and tetrahydropyran,
Trans. Faraday Soc., 1961, 57, 2125-2131. [all data]
Cass, Fletcher, et al., 1958
Cass, R.C.; Fletcher, S.E.; Mortimer, C.T.; Springall, H.D.; White, T.R.,
Heats of combustion and molecular structure. Part V. The mean bond energy term for the C-O bond in ethers, and the structures of some cyclic ethers,
J. Chem. Soc., 1958, 1406-1410. [all data]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]
Dorofeeva O.V., 1992
Dorofeeva O.V.,
Ideal gas thermodynamic properties of oxygen heterocyclic compounds. Part 2. Six-membered, seven-membered and eight-membered rings,
Thermochim. Acta, 1992, 200, 121-150. [all data]
Vedal D., 1975
Vedal D.,
Vibrational spectra of pentamethylene sulfide and selenide,
Spectrochim. Acta, 1975, A31, 355-372. [all data]
Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G.,
Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update,
J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018
. [all data]
Decouzon, Gal, et al., 1996
Decouzon, M.; Gal, J.E.; Herreros, M.; Marai, P.C.; Murrell, J.; Todd, J.F.J.,
On the Use of the Kinetic Method for the Determination of Proton Affinities by Fourier-Transfrom Ion Cyclotron Resonance Mass Spectrometry,
Rapid. Comm. Mass Spectrom., 1996, 10, 242. [all data]
Holmes and Lossing, 1991
Holmes, J.L.; Lossing, F.P.,
Ionization energies of homologous organic compounds and correlation with molecular size,
Org. Mass Spectrom., 1991, 26, 537. [all data]
Behan, Dean, et al., 1976
Behan, J.M.; Dean, F.M.; Johnstone, R.A.W.,
Photoelectron spectra of cyclic aromatic ethers. The question of the Mills-Nixon effect,
Tetrahedron, 1976, 32, 167. [all data]
Hernandez, 1963
Hernandez, G.J.,
Vacuum-ultraviolet absorption spectra of the cyclic ethers: trimethylene oxide, tetrahydrofuran, and tetrahydropyran,
J. Chem. Phys., 1963, 38, 2233. [all data]
Watanabe, Nakayama, et al., 1962
Watanabe, K.; Nakayama, T.; Mottl, J.,
Ionization potentials of some molecules,
J. Quant. Spectry. Radiative Transfer, 1962, 2, 369. [all data]
Kimura, Katsumata, et al., 1981
Kimura, K.; Katsumata, S.; Achiba, Y.; Yamazaki, T.; Iwata, S.,
Ionization energies, Ab initio assignments, and valence electronic structure for 200 molecules
in Handbook of HeI Photoelectron Spectra of Fundamental Organic Compounds, Japan Scientific Soc. Press, Tokyo, 1981. [all data]
Planckaert, Doucet, et al., 1974
Planckaert, A.A.; Doucet, J.; Sandorfy, C.,
Comparative study of the vacuum ultraviolet absorption and photoelectron spectra of some simple ethers and thioethers,
J. Chem. Phys., 1974, 60, 4846. [all data]
Kobayashi and Nagakura, 1973
Kobayashi, T.; Nagakura, S.,
Photoelectron spectra of tetrahydropyran, 1,3-dioxane, and 1,4-dioxane,
Bull. Chem. Soc. Jpn., 1973, 46, 1558. [all data]
Sweigart and Turner, 1972
Sweigart, D.A.; Turner, D.W.,
Lone pair orbitals and their interactions studied by photoelectron spectroscopy. II. Equivalent orbitals in saturated oxygen and sulfur J. Heterocycl. Chem.,
J. Am. Chem. Soc., 1972, 94, 5599. [all data]
Collin and Conde-Caprace, 1966
Collin, J.E.; Conde-Caprace, G.,
Ionization and dissociation of cyclic ethers by electron impact,
Intern. J. Mass Spectrom. Ion Phys., 1966, 1, 213. [all data]
Bogoslovsky, Anvaer, et al., 1978
Bogoslovsky, Yu.N.; Anvaer, B.I.; Vigdergauz, M.S.,
Chromatographic constants in gas chromatography (in Russian), Standards Publ. House, Moscow, 1978, 192. [all data]
Jonas, Janák, et al., 1966
Jonas, J.; Janák, J.; Kratochvíl, M.,
Structural investigations with the aid of Kovats retention index system on one (nonpolar) stationary phase,
J. Gas Chromatogr., 1966, 4, 9, 332-335, https://doi.org/10.1093/chromsci/4.9.332
. [all data]
Jonas, Kratochvíl, et al., 1966
Jonas, J.; Kratochvíl, M.; Gross, H.; Janák, J.,
Über α-halogenäther XXV. Verwendung des Kovatsschen retentionsiondexsystems zur identifizierung von acetalen der tetrahydropyranreihe,
Collect. Czech. Chem. Commun., 1966, 31, 6, 2399-2409, https://doi.org/10.1135/cccc19662399
. [all data]
Wehrli and Kováts, 1959
Wehrli, A.; Kováts, E.,
Gas-chromatographische Charakterisierung ogranischer Verbindungen. Teil 3: Berechnung der Retentionsindices aliphatischer, alicyclischer und aromatischer Verbindungen,
Helv. Chim. Acta, 1959, 7, 7, 2709-2736, https://doi.org/10.1002/hlca.19590420745
. [all data]
Anderson, Jurel, et al., 1973
Anderson, A.; Jurel, S.; Shymanska, M.; Golender, L.,
Gas-liquid chromatography of some aliphatic and heterocyclic mono- and pollyfunctional amines. VII. Retention indices of amines in some polar and unpolar stationary phases,
Latv. PSR Zinat. Akad. Vestis Kim. Ser., 1973, 1, 51-63. [all data]
Kurdina, Markovich, et al., 1969
Kurdina, Z.G.; Markovich, V.E.; Sakharov, V.M.,
Gas chromatography of cyclic O-containing compounds
in Gas chromatography, Issue # 10, NIITEKhim, Moscow, 1969, 128-133. [all data]
Farkas, Héberger, et al., 2004
Farkas, O.; Héberger, K.; Zenkevich, I.G.,
Quantitative structure-retention relationships. XIV. Prediction of gas chromatographic retention indices for saturated O-, N-, and S-heterocyclic compounds,
Chemom. Intell. Lab. Syst., 2004, 72, 2, 173-184, https://doi.org/10.1016/j.chemolab.2004.01.012
. [all data]
Vinogradov, 2004
Vinogradov, B.A.,
Production, composition, properties and application of essential oils, 2004, retrieved from http://viness.narod.ru. [all data]
Zenkevich, 1998
Zenkevich, I.G.,
Reciprocally Unambiguous Conformity Between GC Retention Indices and Boiling Points within Two- and Multidimensional Taxonomic Groups of Organic Compounds,
J. Hi. Res. Chromatogr., 1998, 21, 10, 565-568, https://doi.org/10.1002/(SICI)1521-4168(19981001)21:10<565::AID-JHRC565>3.0.CO;2-6
. [all data]
Waggott and Davies, 1984
Waggott, A.; Davies, I.W.,
Identification of organic pollutants using linear temperature programmed retention indices (LTPRIs) - Part II, 1984, retrieved from http://dwi.defra.gov.uk/research/completed-research/reports/dwi0383.pdf. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, Gas Chromatography, References
- Symbols used in this document:
AE Appearance energy Cp,gas Constant pressure heat capacity of gas IE (evaluated) Recommended ionization energy ΔcH°gas Enthalpy of combustion of gas at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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