Isoxazole
- Formula: C3H3NO
- Molecular weight: 69.0620
- IUPAC Standard InChIKey: CTAPFRYPJLPFDF-UHFFFAOYSA-N
- CAS Registry Number: 288-14-2
- 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: 1-Oxa-2-azacyclopentadiene; Isooxazole
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Gas phase thermochemistry data
Go To: Top, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | 19.6 ± 0.1 | kcal/mol | Ccr | Steele, Chirico, et al., 1996 | |
ΔfH°gas | 18.78 ± 0.13 | kcal/mol | Ccb | McCormick and Hamilton, 1978 | see McCormick, 1977 |
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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 367.2 | K | N/A | Aldrich Chemical Company Inc., 1990 | BS |
Tboil | 368.7 | K | N/A | Weast and Grasselli, 1989 | BS |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 590. | K | N/A | Steele, Chirico, et al., 1996, 2 | Uncertainty assigned by TRC = 3. K; fitting parameter in Wagner equation for vapor pressure; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 60.20 | atm | N/A | Steele, Chirico, et al., 1996, 2 | Uncertainty assigned by TRC = 3.95 atm; from extrapolation of obs. vapor pressure to Tc; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ρc | 5.237 | mol/l | N/A | Steele, Chirico, et al., 1996, 2 | Uncertainty assigned by TRC = 0.29 mol/l; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 8.901 ± 0.053 | kcal/mol | V | Steele, Chirico, et al., 1996 | ALS |
ΔvapH° | 8.89 ± 0.05 | kcal/mol | EB | Steele, Chirico, et al., 1996 | Based on data from 314. to 404. K.; AC |
ΔvapH° | 8.71 ± 0.01 | kcal/mol | C | McCormick and Hamilton, 1978 | see McCormick, 1977; ALS |
ΔvapH° | 8.72 ± 0.02 | kcal/mol | C | McCormick and Hamilton, 1978 | 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:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 10. ± 0.1 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 202.8 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 195.2 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.93 ± 0.05 | EI | Bouchoux and Hoppilliard, 1981 | LLK |
9.99 ± 0.05 | PE | Baker, Betteridge, et al., 1970 | RDSH |
10.20 | PE | Daamen, Oskam, et al., 1979 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
HCO+ | 13.62 | ? | EI | Bouchoux and Hoppilliard, 1981 | LLK |
CNO+ | 12.24 | C2H3 | EI | Bouchoux and Hoppilliard, 1981 | LLK |
C2H2N+ | 13.34 | HCO | EI | Bouchoux and Hoppilliard, 1981 | LLK |
C2H3N+ | 11.34 ± 0.05 | CO | EI | Buschek, Holmes, et al., 1986 | LBLHLM |
C2H3N+ | 11.80 | CO | EI | Bouchoux and Hoppilliard, 1981 | LLK |
C3H2NO+ | 11.24 | H | EI | Bouchoux and Hoppilliard, 1981 | 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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Due to licensing restrictions, this spectrum cannot be downloaded.
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-7367 |
NIST MS number | 233403 |
Gas Chromatography
Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), 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 |
---|---|---|---|---|---|
Capillary | OV-101 | 110. | 590. | Zhuravleva, 2000 | 50. m/0.3 mm/0.4 μm, He |
Capillary | OV-101 | 110. | 590. | Golovnya, Kuz'menko, et al., 1999 | 50. m/0.3 mm/0.4 μm, He |
References
Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Steele, Chirico, et al., 1996
Steele, W.V.; Chirico, R.D.; Knipmeyer, S.E.; Nguyen, A.; Smith, N.K.; Tasker, I.R.,
Thermodynamic properties and ideal-gas enthalpies of formation for cyclohexene, phthalan (2,5-dihydrobenzo-3,4-furan), isoxazole, octylamine, dioctylamine, trioctylamine, phenyl isocyanate, and 1,4,5,6-tetrahydropyrimidine,
J. Chem. Eng. Data, 1996, 41, 1269-1284. [all data]
McCormick and Hamilton, 1978
McCormick, D.G.; Hamilton, W.S.,
The enthalpies of combustion and formation of oxazole and isoxazole,
J. Chem. Thermodyn., 1978, 10, 275-278. [all data]
McCormick, 1977
McCormick, D.G.,
The resonance energies of oxazole and isoxazole determined from the enthalpies of combustion and formation (Order No. 7801771),
Diss. Abstr. Int. B, 1977, 38, 4271. [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]
Steele, Chirico, et al., 1996, 2
Steele, W.V.; Chirico, R.D.; Knipmeyer, S.E.; Nguyen, A.; Smith, N.K.; Tasker, I.R.,
Thermodynamic Properties and Ideal-Gas Enthalpies of Formation for Dioctylamine, trioctylamine, Phenyl Isocyanate, and 1,4,5,6-Tetrahydropyrimidine,
J. Chem. Eng. Data, 1996, 41, 1269-84. [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]
Bouchoux and Hoppilliard, 1981
Bouchoux, G.; Hoppilliard, Y.,
Fragmentation mechanisms of isoxazole,
Org. Mass Spectrom., 1981, 16, 459. [all data]
Baker, Betteridge, et al., 1970
Baker, A.D.; Betteridge, D.; Kemp, N.R.; Kirby, R.E.,
Application of photoelectron spectrometry to pesticide analysis. Photoelectron spectra of fivemembered heterocycles and related molecules,
Anal. Chem., 1970, 42, 1064. [all data]
Daamen, Oskam, et al., 1979
Daamen, H.; Oskam, A.; Stufkens, D.J.; Waaijers, H.W.,
Bonding properties of group VIB metal pentacarbonyl azole complexes studied by electronic absorption, photoelectron, 13C NMR and vibrational spectroscopy,
Inorg. Chim. Acta, 1979, 34, 253. [all data]
Buschek, Holmes, et al., 1986
Buschek, J.M.; Holmes, J.L.; Lossing, F.P.,
The mass spectrometric generation of neutral ethynamine HC≡CNH2 and C2H3N isomers.,
Org. Mass Spectrom., 1986, 21, 729. [all data]
Zhuravleva, 2000
Zhuravleva, I.L.,
Evaluation of the polarity and boiling points of nitrogen-containing heterocyclic compounds by gas chromatography,
Russ. Chem. Bull. (Engl. Transl.), 2000, 49, 2, 325-328, https://doi.org/10.1007/BF02494682
. [all data]
Golovnya, Kuz'menko, et al., 1999
Golovnya, R.V.; Kuz'menko, T.E.; Zhuravleva, I.L.,
Gas chromatographic indicator of the ability of five- and six-membered heterocyclic nitrogen-containing compounds for self-association in pure liquids,
Russ. Chem. Bull. (Engl. Transl.), 1999, 48, 4, 726-729, https://doi.org/10.1007/BF02496256
. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, References
- Symbols used in this document:
AE Appearance energy IE (evaluated) Recommended ionization energy Pc Critical pressure Tboil Boiling point Tc Critical temperature ΔfH°gas Enthalpy of formation of gas at standard conditions ΔvapH° Enthalpy of vaporization at standard conditions ρc Critical density - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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