Trimethylene oxide
- Formula: C3H6O
- Molecular weight: 58.0791
- IUPAC Standard InChIKey: AHHWIHXENZJRFG-UHFFFAOYSA-N
- 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
The 3d structure may be viewed using Java or Javascript. - 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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Gas phase ion energetics data
Go To: Top, 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:
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)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 9.65 ± 0.01 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 801.3 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 773.9 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.65 | PE | Roszak, Kaufman, et al., 1992 | LL |
9.64 ± 0.05 | EI | Holmes and Lossing, 1991 | LL |
9.6 | PE | Aue and Bowers, 1979 | LLK |
9.63 | PE | Mollere, 1973 | LLK |
9.668 ± 0.005 | S | Hernandez, 1963 | RDSH |
9.679 | PE | Aue, Webb, et al., 1975 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
CHO+ | 12.6 ± 0.2 | ? | EI | Gallegos and Kiser, 1962 | RDSH |
CH3O+ | 13.3 ± 0.2 | ? | EI | Gallegos and Kiser, 1962 | RDSH |
C2H2+ | 15.2 ± 0.2 | ? | EI | Gallegos and Kiser, 1962 | RDSH |
C2H3+ | 14.9 ± 0.3 | ? | EI | Gallegos and Kiser, 1962 | RDSH |
C2H4+ | 12.4 ± 0.3 | ? | EI | Gallegos and Kiser, 1962 | RDSH |
C2H5+ | 12.6 ± 0.2 | ? | EI | Gallegos and Kiser, 1962 | RDSH |
C2H6+ | 10.8 ± 0.3 | CO | EI | Gallegos and Kiser, 1962 | RDSH |
C3H5+ | 11.8 ± 0.2 | OH | EI | Gallegos and Kiser, 1962 | RDSH |
Gas Chromatography
Go To: Top, 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. | 539. | Bogoslovsky, Anvaer, et al., 1978 | Celite 545 |
Packed | Apiezon L | 160. | 544. | Bogoslovsky, Anvaer, et al., 1978 | Celite 545 |
Packed | SE-30 | 125. | 543. | Casteignau and Halary, 1972 | Chromosorb P (60-80 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. | 542. | 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 | 553. | Farkas, Héberger, et al., 2004 | Program: not specified |
References
Go To: Top, 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.
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]
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]
Casteignau and Halary, 1972
Casteignau, G.; Halary, J.-L.,
No. 72 - Identification et dosage par chromatographie en phase gazeuse d'oxetannes disubstitués en 3 et de quelques autres éthers-oxydes,
Bull. Soc. Chim. Fr., 1972, 1, 420-428. [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]
Notes
Go To: Top, Gas phase ion energetics data, Gas Chromatography, References
- Symbols used in this document:
AE Appearance energy IE (evaluated) Recommended ionization energy - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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