Trimethylene oxide

• Formula: C₃H₆O
• Molecular weight: 58.0791
• IUPAC Standard InChI: InChI=1S/C3H6O/c1-2-4-3-1/h1-3H2 Copy

  
• IUPAC Standard InChIKey: AHHWIHXENZJRFG-UHFFFAOYSA-N Copy
• CAS Registry Number: 503-30-0
• 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: Oxetane; α,γ-Propane oxide; Cyclooxabutane; Oxacyclobutane; Propane, 1,3-epoxy-; 1,3-Epoxypropane; 1,3-Propylene oxide; 1,3-Trimethylene oxide; Trimethylenoxid; Oxetan; NSC 30086; 1,2-epoxypropane
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• Information on this page:
  • Phase change data
  • Gas phase ion energetics data
  • IR Spectrum
  • UV/Visible spectrum
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Mass spectrum (electron ionization)
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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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

Enthalpy of vaporization

Enthalpy of vaporization

Δ_vapH = A exp(-βT_r) (1 − T_r)^β
    Δ_vapH = Enthalpy of vaporization (at saturation pressure) (kJ/mol)
    T_r = reduced temperature (T / T_c)

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Enthalpy of fusion

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:
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 C₃H₆O⁺ (ion structure unspecified)

Ionization energy determinations

Appearance energy determinations

IR Spectrum

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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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Gas Phase Spectrum

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Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.

Additional Data

UV/Visible spectrum

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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 by: Victor Talrose, Eugeny B. Stern, Antonina A. Goncharova, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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Additional Data

References

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc., Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]

Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [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]

Chan, Zinn, et al., 1960
Chan, S.I.; Zinn, J.; Fernandez, J.; Gwinn, W.D., Trimethylene Oxide. I. Microwave Spectrum, Dipole Moment, and Double Minimum Vibration, J. Chem. Phys., 1960, 33, 1643. [all data]

Allen and Hibbert, 1934
Allen, J.S.; Hibbert, H., Studies on reactions relating to carbohydrates and polysaccharides: xlvii the oxygen valence angle and the structure of glucose and related compounds, J. Am. Chem. Soc., 1934, 56, 1398. [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]

Hossenlopp and Scott, 1981
Hossenlopp, I.A.; Scott, D.W., Vapor heat capacities and enthalpies of vaporizaiton of six organic compounds, J. Chem. Thermodyn., 1981, 13, 405-414. [all data]

Handa, 1985
Handa, Y.P., A calorimetric study of trimethylene oxide and its structure I and structure II clathrate hydrates in the temperature range 85 to 270 K, Can. J. Chem., 1985, 63, 1, 68-70, https://doi.org/10.1139/v85-012 . [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]

Roszak, Kaufman, et al., 1992
Roszak, S.; Kaufman, J.J.; Koski, W.S.; Barreto, R.D.; Fehlner, T.P.; Balasubramanian, K., Experimental and theoretical studies of photoelectron spectra of oxetane and some of its halogenated methyl derivatives, J. Phys. Chem., 1992, 96, 7226. [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]

Aue and Bowers, 1979
Aue, D.H.; Bowers, M.T., Chapter 9. Stabilities of positive ions from equilibrium gas phase basicity measurements in Ions Chemistry,, ed. M.T. Bowers, 1979. [all data]

Mollere, 1973
Mollere, P.D., The photoelectron spectrum of oxetane: nondegenerate Walsh orbitals in a four-membered heterocycle, Tetrahedron Lett., 1973, 2791. [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]

Aue, Webb, et al., 1975
Aue, D.H.; Webb, H.M.; Bowers, M.T., Proton affinities, ionization potentials, and hydrogen affinities of nitrogen and oxygen bases. Hybridization effects, J. Am. Chem. Soc., 1975, 97, 4137. [all data]

Gallegos and Kiser, 1962
Gallegos, E.J.; Kiser, R.W., Electron impact spectroscopy of the four- and five-membered, saturated heterocyclic compounds containing nitrogen, oxygen and sulfur, J. Phys. Chem., 1962, 66, 136. [all data]

Fleming, Anderson, et al., 1959
Fleming, G.; Anderson, M.M.; Harrison, A.J.; Pickett, L.W., Effect of ring size on the far ultraviolet absorption and photolysis of cyclic ethers, J. Chem. Phys., 1959, 30, 2, 351-354. [all data]

Notes

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• Symbols used in this document:
  

  AE	Appearance energy
  IE (evaluated)	Recommended ionization energy
  Tboil	Boiling point
  Tc	Critical temperature
  Tfus	Fusion (melting) point
  ΔfusH	Enthalpy of fusion
  ΔvapH	Enthalpy of vaporization
  ΔvapH°	Enthalpy of vaporization at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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