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 thermochemistry data
Go To: Top, Phase change data, Gas phase ion energetics data, IR Spectrum, 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 | -19.25 | kcal/mol | Cm | Douslin, Scott, et al., 1976 | ALS |
ΔfH°gas | -19.25 ± 0.15 | kcal/mol | Cm | Pell and Pilcher, 1965 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°gas | -467.85 ± 0.14 | kcal/mol | Cm | Pell and Pilcher, 1965 | Corresponding ΔfHºgas = -19.25 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
Constant pressure heat capacity of gas
Cp,gas (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
9.070 | 50. | Dorofeeva O.V., 1992 | p=1 bar. Selected values of Cp(T) coincide with the calorimetric values within 0.3 J/mol*K. The value of -(G-Ho)/T at 298.15 K obtained from absolute intensity measurements in the microwave spectrum [ Curl R.F., 1973] differs by only 0.2 J/mol*K from the value calculated by [ Dorofeeva O.V., 1992, 2]. Discrepancies with the Cp(T) and S(T) values calculated by [ Zurcher R.F., 1955, Zurcher R.F., 1957] amount to 2-10 J/mol*K.; GT |
9.209 | 100. | ||
9.551 | 150. | ||
10.59 | 200. | ||
13.48 | 273.15 | ||
14.71 ± 0.48 | 298.15 | ||
14.80 | 300. | ||
20.07 | 400. | ||
24.914 | 500. | ||
28.994 | 600. | ||
32.390 | 700. | ||
35.239 | 800. | ||
37.651 | 900. | ||
39.704 | 1000. | ||
41.460 | 1100. | ||
42.966 | 1200. | ||
44.264 | 1300. | ||
45.382 | 1400. | ||
46.350 | 1500. |
Constant pressure heat capacity of gas
Cp,gas (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
14.63 ± 0.029 | 298.15 | Hossenlopp I.A., 1981 | GT |
15.93 ± 0.031 | 323.15 | ||
17.25 ± 0.033 | 348.15 | ||
18.60 ± 0.036 | 373.15 | ||
19.92 ± 0.041 | 398.15 | ||
21.20 ± 0.043 | 423.15 | ||
22.48 ± 0.045 | 448.15 | ||
23.68 ± 0.048 | 473.15 | ||
24.840 ± 0.050 | 498.15 | ||
25.968 ± 0.053 | 523.15 |
Phase change data
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, IR Spectrum, 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:
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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 323.2 | K | N/A | Aldrich Chemical Company Inc., 1990 | BS |
Tboil | 320.7 | K | N/A | Weast and Grasselli, 1989 | BS |
Tboil | 320.8 | K | N/A | Majer and Svoboda, 1985 | |
Tboil | 321.65 | K | N/A | Chan, Zinn, et al., 1960 | Uncertainty assigned by TRC = 0.5 K; TRC |
Tboil | 320.9 | K | N/A | Allen and Hibbert, 1934 | Uncertainty assigned by TRC = 1. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 176.15 | K | N/A | Brooks and Pilcher, 1959 | Uncertainty assigned by TRC = 1. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 507.9 | K | N/A | Majer and Svoboda, 1985 | |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 7.220 | kcal/mol | N/A | Majer and Svoboda, 1985 | |
ΔvapH° | 7.12 | kcal/mol | C | Hossenlopp and Scott, 1981 | AC |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
6.852 | 320.8 | Majer and Svoboda, 1985 |
Enthalpy of vaporization
ΔvapH =
A exp(-βTr) (1 − Tr)β
ΔvapH =
Enthalpy of vaporization (at saturation pressure)
(kcal/mol)
Tr = reduced temperature (T / Tc)
View plot Requires a JavaScript / HTML 5 canvas capable browser.
Temperature (K) | A (kcal/mol) | β | Tc (K) | Reference | Comment |
---|---|---|---|---|---|
272. to 342. | 10.35 | 0.2532 | 507.9 | Majer and Svoboda, 1985 |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
1.50 | 173.2 | Handa, 1985 | Based on data from 85. to 270. K.; AC |
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)
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) | 191.5 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 185.0 | kcal/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 |
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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Additional Data
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Owner | NIST Standard Reference Data Program Collection (C) 2018 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | NIST Mass Spectrometry Data Center |
State | gas |
Instrument | HP-GC/MS/IRD |
Gas Chromatography
Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, 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 thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Douslin, Scott, et al., 1976
Douslin, D.R.; Scott, D.W.; Good, W.D.; Osborn, A.G.,
Thermodynamic properties of organic compounds and thermodynamic properties of fluids,
Gov. Rep. Announce. Index U.S., 1976, 76, 97. [all data]
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]
Dorofeeva O.V., 1992
Dorofeeva O.V.,
Ideal gas thermodynamic properties of oxygen heterocyclic compounds. Part 1. Three-membered, four-membered and five-membered rings,
Thermochim. Acta, 1992, 194, 9-46. [all data]
Curl R.F., 1973
Curl R.F.,
Determination of thermodynamic functions from absolute intensity measurements in microwave spectroscopy,
J. Am. Chem. Soc., 1973, 95, 6182-6190. [all data]
Dorofeeva O.V., 1992, 2
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]
Zurcher R.F., 1955
Zurcher R.F.,
Vibrational spectra and thermodynamic properties of trimethylene oxide,
Helv. Chim. Acta, 1955, 38, 849-865. [all data]
Zurcher R.F., 1957
Zurcher R.F.,
Raman spectrum, normal coordinate analysis and thermodynamic properties of trimethylene oxide. II,
Helv. Chim. Acta, 1957, 40, 89-101. [all data]
Hossenlopp I.A., 1981
Hossenlopp I.A.,
Vapor heat capacities and enthalpies of vaporization of six organic compounds,
J. Chem. Thermodyn., 1981, 13, 405-414. [all data]
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]
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 thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Gas Chromatography, References
- Symbols used in this document:
AE Appearance energy Cp,gas Constant pressure heat capacity of gas IE (evaluated) Recommended ionization energy Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point ΔcH°gas Enthalpy of combustion of gas at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions 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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