Oxirane, 2,3-dimethyl-, trans-
- Formula: C4H8O
- Molecular weight: 72.1057
- IUPAC Standard InChIKey: PQXKWPLDPFFDJP-IMJSIDKUSA-N
- CAS Registry Number: 21490-63-1
- 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. - Species with the same structure:
- Stereoisomers:
- Other names: Butane, 2,3-epoxy-, trans-; trans-2-Butene Oxide; trans-2-Butylene Oxide; trans-2,3-Dimethyloxirane; trans-2,3-Epoxybutane; 2,3-Butylene oxide (trans); 2,3-Dimethyloxirane, trans; 2,3-Dimethyl-oxirane (E)
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Gas 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 by: Glushko Thermocenter, Russian Academy of Sciences, Moscow
Constant pressure heat capacity of gas
Cp,gas (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
48.53 | 100. | Durig J.R., 1982 | The impression is formed that authors did not take into account the existence of optical isomers for trans-isomer. In this case, the Rln2 (5.76 J/mol*K) should be added to values of S(T). |
73.22 | 200. | ||
98.32 | 298.15 | ||
124.68 | 400. | ||
147.28 | 500. | ||
166.52 | 600. | ||
182.84 | 700. | ||
196.65 | 800. | ||
208.78 | 900. | ||
218.82 | 1000. |
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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 327.7 | K | N/A | Aldrich Chemical Company Inc., 1990 | BS |
Tboil | 327. to 328. | K | N/A | Farchan Laboratories, 1990 | BS |
Tboil | 330.15 | K | N/A | Cottle and Powell, 1936 | Uncertainty assigned by TRC = 3. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 190.55 | K | N/A | Timmermans, 1952 | Uncertainty assigned by TRC = 0.5 K; TRC |
Tfus | 188.15 | K | N/A | Wilson and Lucas, 1936 | Uncertainty assigned by TRC = 6. K; TRC |
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 compiled as indicated in comments:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
View reactions leading to C4H8O+ (ion structure unspecified)
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.98 | PE | McAlduff and Houk, 1977 | Vertical value; LLK |
Mass spectrum (electron ionization)
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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
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. |
---|---|
NIST MS number | 296 |
Gas Chromatography
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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
Kovats' RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | OV-101 | 70. | 544. | Tarjan, Nyiredy, et al., 1989 | |
Capillary | OV-101 | 80. | 544. | Tarjan, Nyiredy, et al., 1989 | |
Capillary | OV-101 | 90. | 544. | Tarjan, Nyiredy, et al., 1989 | |
Capillary | OV-101 | 70. | 543.5 | Boneva and Dimov, 1987 | 100. m/0.27 mm/0.9 μm |
Capillary | OV-101 | 80. | 543.6 | Boneva and Dimov, 1987 | 100. m/0.27 mm/0.9 μm |
Capillary | OV-101 | 90. | 543.7 | Boneva and Dimov, 1987 | 100. m/0.27 mm/0.9 μm |
Packed | Apiezon L | 120. | 518. | Bogoslovsky, Anvaer, et al., 1978 | Celite 545 |
Packed | Apiezon L | 160. | 517. | Bogoslovsky, Anvaer, et al., 1978 | Celite 545 |
Normal alkane RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Packed | Apieson L | 120. | 520. | 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 | 574. | Farkas, Héberger, et al., 2004 | Program: not specified |
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.
Durig J.R., 1982
Durig J.R.,
Vibrational spectra and torsional analysis of cis-2,3-dimethyloxirane and trans-2,3-dimethyloxirane,
J. Mol. Struct., 1982, 95, 59-84. [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]
Farchan Laboratories, 1990
Farchan Laboratories,
Research Chemicals Catalog, Farchan Laboratories, Gainesville, FL, 1990, 91. [all data]
Cottle and Powell, 1936
Cottle, D.L.; Powell, L.S.,
The Reaction of 2,3-Epoxybutane with Grignard Reagent,
J. Am. Chem. Soc., 1936, 58, 2267. [all data]
Timmermans, 1952
Timmermans, J.,
Freezing points of organic compounds. VVI New determinations.,
Bull. Soc. Chim. Belg., 1952, 61, 393. [all data]
Wilson and Lucas, 1936
Wilson, C.E.; Lucas, H.J.,
Stereochemical Relationships of the Isomeric 2,3-Butanediols and Related Compounds; Evidence of Walden Inversion,
J. Am. Chem. Soc., 1936, 58, 2396. [all data]
McAlduff and Houk, 1977
McAlduff, E.J.; Houk, K.N.,
Photoelectron spectra of substituted oxiranes and thiiranes. Substituent effects on ionization potentials involving σ orbitals,
Can. J. Chem., 1977, 55, 318. [all data]
Tarjan, Nyiredy, et al., 1989
Tarjan, G.; Nyiredy, Sz.; Gyor, M.; Lombosi, E.R.; Lombosi, T.S.; Budahegyi, M.V.; Meszaros, S.Y.; Takacs, J.M.,
Review. Thirtieth Anniversary of the Retention Index According to Kovats in Gas-Liquid Chromatography,
J. Chromatogr., 1989, 472, 1-92, https://doi.org/10.1016/S0021-9673(00)94099-8
. [all data]
Boneva and Dimov, 1987
Boneva, S.; Dimov, N.,
Gas chromatographic separation of C4-C5 epoxides on a glass capillary column coated with OV-101 methylsilicone,
Chromatographia, 1987, 23, 10, 770-772, https://doi.org/10.1007/BF02312672
. [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]
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
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- Symbols used in this document:
Cp,gas Constant pressure heat capacity of gas Tboil Boiling point Tfus Fusion (melting) point - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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