Tetrahydropyran

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Condensed phase 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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Δfliquid-60.9 ± 0.4kcal/molCcbSnelson and Skinner, 1961ALS
Quantity Value Units Method Reference Comment
Δcliquid-750.94 ± 0.31kcal/molCcbSnelson and Skinner, 1961Corresponding Δfliquid = -60.89 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δcliquid-752.8 ± 1.5kcal/molCcbCass, Fletcher, et al., 1958Corresponding Δfliquid = -59.0 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δcliquid-749.90 ± 0.20kcal/molCcbSkuratov, Strepikheev, et al., 1957Reanalyzed by Cox and Pilcher, 1970, Original value = -750.1 ± 0.2 kcal/mol; Combustion at 293 K; Corresponding Δfliquid = -61.93 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS

Constant pressure heat capacity of liquid

Cp,liquid (cal/mol*K) Temperature (K) Reference Comment
35.755298.15Inglese, Grolier, et al., 1984DH
35.662298.15Inglese, Castagnolo, et al., 1981DH
33.60298.Conti, Gianni, et al., 1976DH
36.121297.62Moelwyn-Hughes and Thorpe, 1964T = 297 to 327 K.; DH

Phase change 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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Tboil361.0 ± 0.7KAVGN/AAverage of 8 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus224.KN/AGuieu, Carbonnel, et al., 1985Crystal phase 1 phase; Uncertainty assigned by TRC = 0.1 K; TRC
Tfus224.15KN/ABrooks and Pilcher, 1959Uncertainty assigned by TRC = 1. K; TRC
Tfus223.95KN/AAnonymous, 1942Uncertainty assigned by TRC = 0.3 K; TRC
Quantity Value Units Method Reference Comment
Tc572.2KN/AKobe and Mathews, 1970Uncertainty assigned by TRC = 0.3 K; TRC
Quantity Value Units Method Reference Comment
Pc47.08atmN/AKobe and Mathews, 1970Uncertainty assigned by TRC = 0.1399 atm; TRC
Quantity Value Units Method Reference Comment
ρc3.8124mol/lN/AKobe and Mathews, 1970Uncertainty assigned by TRC = 0.0056 mol/l; TRC
Quantity Value Units Method Reference Comment
Δvap8.286kcal/molN/AMajer and Svoboda, 1985 
Δvap9.13 ± 0.26kcal/molDSCRojas-Aguilar, Ginez-Carbajal, et al., 2005AC
Δvap8.37kcal/molN/ASnelson and Skinner, 1961DRB
Δvap8.35kcal/molVCass, Fletcher, et al., 1958ALS

Enthalpy of vaporization

ΔvapH (kcal/mol) Temperature (K) Method Reference Comment
7.450361.N/AMajer and Svoboda, 1985 
8.6301.N/ARodríguez, Giner, et al., 2006Based on data from 286. to 361. K.; AC
7.93350.N/ARodriguez, Artigas, et al., 2000Based on data from 335. to 412. K.; AC
8.37288.AStephenson and Malanowski, 1987Based on data from 273. to 362. K.; AC
8.37281.N/ADykyj, 1972Based on data from 273. to 288. K. See also Cass, Fletcher, et al., 1958, 2.; AC
8.5293.VSkuratov, Strepikheev, et al., 1957Combustion at 293 K; ALS

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


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 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 ± 0.01eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)196.7kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity190.1kcal/molN/AHunter and Lias, 1998HL

Gas basicity at 298K

Gas basicity (review) (kcal/mol) Reference Comment
191.0 ± 0.02Decouzon, Gal, et al., 1996T = 338K; MM
191.0Decouzon, Gal, et al., 1996T = T(eff) = 430K; MM

Ionization energy determinations

IE (eV) Method Reference Comment
9.24 ± 0.05EIHolmes and Lossing, 1991LL
9.16PEBehan, Dean, et al., 1976LLK
9.25 ± 0.01SHernandez, 1963RDSH
9.26 ± 0.03PIWatanabe, Nakayama, et al., 1962RDSH
9.57PEKimura, Katsumata, et al., 1981Vertical value; LLK
9.46PEPlanckaert, Doucet, et al., 1974Vertical value; LLK
9.48PEKobayashi and Nagakura, 1973Vertical value; LLK
9.50PESweigart and Turner, 1972Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C2H4+~13.8?EICollin and Conde-Caprace, 1966RDSH
C2H5O+11.56?EICollin and Conde-Caprace, 1966RDSH
C3H5+~12.8?EICollin and Conde-Caprace, 1966RDSH
C4H7+~12.2CH2O+HEICollin and Conde-Caprace, 1966RDSH
C4H8+11.88CH2O?EICollin and Conde-Caprace, 1966RDSH
C5H9O+11.22HEICollin and Conde-Caprace, 1966RDSH

Mass spectrum (electron ionization)

Go To: Top, Condensed phase thermochemistry data, Phase change 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

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 Japan AIST/NIMC Database- Spectrum MS-NW-1046
NIST MS number 229215

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References

Go To: Top, Condensed phase thermochemistry data, Phase change 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.

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]

Skuratov, Strepikheev, et al., 1957
Skuratov, S.M.; Strepikheev, A.A.; Kozina, M.P., About the reaction activity of five and six-membered heterocyclic compounds, Dokl. Akad. Nauk SSSR, 1957, 117, 452-454. [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]

Inglese, Grolier, et al., 1984
Inglese, A.; Grolier, J.-P.E.; Wilhelm, E., Excess volumes and excess heat capacities of oxane + cyclohexane and 1,4-dioxane + cyclohexane, Fluid Phase Equilibria, 1984, 15, 287-294. [all data]

Inglese, Castagnolo, et al., 1981
Inglese, A.; Castagnolo, M.; Dell'Atti, A.; DeGiglio, A., Thermochim. Acta, 1981, 77-87. [all data]

Conti, Gianni, et al., 1976
Conti, G.; Gianni, P.; Matteoli, E.; Mengheri, M., Capacita termiche molari di alcuni composti organici mono- e bifunzionali nel liquido puro e in soluzione acquosa a 25C, Chim. Ind. (Milan), 1976, 58, 225. [all data]

Moelwyn-Hughes and Thorpe, 1964
Moelwyn-Hughes, E.A.; Thorpe, P.L., The physical and thermodynamic properties of some associated solutions. II. Heat capacities and compressibilities, Proc. Roy. Soc. (London), 1964, 278A, 574-587. [all data]

Guieu, Carbonnel, et al., 1985
Guieu, R.; Carbonnel, L.; Kehiaian, H.V., Solutions solides organiques I. Etude des diagrammes de phases des systemes oxanne ou 1,4-dioxanne + cyclohexane, Bull. Soc. Chim. Fr., 1985, 1985, 709. [all data]

Brooks and Pilcher, 1959
Brooks, J.H.; Pilcher, G., A Simple Melting Point Calorimeter for Moderately Precise Determination of Purity, J. Chem. Soc., 1959, 1959, 1535. [all data]

Anonymous, 1942
Anonymous, R., , Am. Pet. Inst. Res. Proj. 6, Natl. Bur. Stand., 1942. [all data]

Kobe and Mathews, 1970
Kobe, K.A.; Mathews, J.F., Critical Properties and Vapor Pressures of Some Organic Nitrogen and Oxygen Compounds, J. Chem. Eng. Data, 1970, 15, 182. [all data]

Majer and Svoboda, 1985
Majer, V.; Svoboda, V., Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [all data]

Rojas-Aguilar, Ginez-Carbajal, et al., 2005
Rojas-Aguilar, A.; Ginez-Carbajal, F.; Orozco-Guareno, E.; Flores-Segura, H., Measurement of enthalpies of vaporization of volatile heterocyclic compounds by DSC, J Therm Anal Calorim, 2005, 79, 1, 95-100, https://doi.org/10.1007/s10973-004-0568-3 . [all data]

Rodríguez, Giner, et al., 2006
Rodríguez, S.; Giner, B.; Haro, M.; Martín, S.; Artigas, H., Isobaric vapour--liquid equilibrium for the binary systems formed by a cyclic ether and bromocyclohexane at 40.0 and 101.3 kPa, Physics and Chemistry of Liquids, 2006, 44, 3, 275-285, https://doi.org/10.1080/00319100600574168 . [all data]

Rodriguez, Artigas, et al., 2000
Rodriguez, S.; Artigas, H.; Lafuente, C.; Mainar, A.M.; Royo, F.M., Isobaric vapour--liquid equilibrium of binary mixtures of some cyclic ethers with chlorocyclohexane at 40.0 and 101.3 kPa, Thermochimica Acta, 2000, 362, 1-2, 153-160, https://doi.org/10.1016/S0040-6031(00)00580-3 . [all data]

Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw, Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2 . [all data]

Dykyj, 1972
Dykyj, J., Petrochemia, 1972, 12, 1, 13. [all data]

Cass, Fletcher, et al., 1958, 2
Cass, R.C.; Fletcher, S.E.; Mortimer, C.T.; Quincey, P.G.; Springall, H.D., 193. Heats of combustion and molecular structure. Part IV. Aliphatic nitroalkanes and nitric esters, J. Chem. Soc., 1958, 958, https://doi.org/10.1039/jr9580000958 . [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]


Notes

Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), References