1-Propene, 3-methoxy-
- Formula: C4H8O
- Molecular weight: 72.1057
- IUPAC Standard InChIKey: FASUFOTUSHAIHG-UHFFFAOYSA-N
- CAS Registry Number: 627-40-7
- 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: Ether, allyl methyl; Allyl methyl ether; Methyl allyl ether; Methyl 2-propenyl ether; 1-Methoxy-2-propene; 3-Methoxypropene; 4-Oxapent-1-ene; CH2=CHCH2OCH3; 3-Methoxy-1-propene
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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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 319.2 | K | N/A | Weast and Grasselli, 1989 | BS |
Tboil | 319.15 | K | N/A | Katritzky, Pinzelli, et al., 1970 | Uncertainty assigned by TRC = 2. K; TRC |
Tboil | 320. | K | N/A | Shikhmamedbekova and Sultanov, 1970 | Uncertainty assigned by TRC = 3. K; TRC |
Reaction 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 as indicated in comments:
B - John E. Bartmess
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.
Individual Reactions
C4H7O- + =
By formula: C4H7O- + H+ = C4H8O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 388.7 ± 4.1 | kcal/mol | G+TS | Dahlke and Kass, 1991 | gas phase; Between H2O, furan. Reprotonation site uncertain; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 382.0 ± 4.0 | kcal/mol | IMRB | Dahlke and Kass, 1991 | gas phase; Between H2O, furan. Reprotonation site uncertain; B |
By formula: C4H8O = C4H8O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -4.83 ± 0.05 | kcal/mol | Eqk | Taskinen, 1993 | liquid phase; solvent: DMSO; Isomerization; ALS |
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:
B - John E. Bartmess
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
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 |
---|---|---|---|
9.56 | EI | Holmes and Lossing, 1986 | LBLHLM |
9.84 ± 0.05 | PE | McAlduff, Caramella, et al., 1978 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C2H5O+ | 10.74 ± 0.05 | C2H3 | EI | Holmes and Lossing, 1984 | LBLHLM |
De-protonation reactions
C4H7O- + =
By formula: C4H7O- + H+ = C4H8O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 388.7 ± 4.1 | kcal/mol | G+TS | Dahlke and Kass, 1991 | gas phase; Between H2O, furan. Reprotonation site uncertain; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 382.0 ± 4.0 | kcal/mol | IMRB | Dahlke and Kass, 1991 | gas phase; Between H2O, furan. Reprotonation site uncertain; B |
IR Spectrum
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Data compiled by: Coblentz Society, Inc.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
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
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | OV-101 | 529. | Zenkevich, 2005 | 25. m/0.20 mm/0.10 μm, N2/He, 6. K/min; Tstart: 50. C; Tend: 250. C |
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.
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]
Katritzky, Pinzelli, et al., 1970
Katritzky, A.R.; Pinzelli, R.F.; Sinnot, M.V.; Topsom, R.D.,
Infrared INtensities as a Quantitative Measure of Intramoelcular Inter- actions XV. Monosubstituted Ethylenes,
J. Am. Chem. Soc., 1970, 92, 6861. [all data]
Shikhmamedbekova and Sultanov, 1970
Shikhmamedbekova, A.Z.; Sultanov, R.A.,
Addition of α-Chloromethyl Ethersto Trialkylenylsilanes,
Zh, Obshch, Khim., 1970, 40, 77-84. [all data]
Dahlke and Kass, 1991
Dahlke, G.D.; Kass, S.R.,
Substituent Effects in the Gas Phase - 1-Substituted Allyl Anions,
J. Am. Chem. Soc., 1991, 113, 15, 5566, https://doi.org/10.1021/ja00015a008
. [all data]
Taskinen, 1993
Taskinen, E.,
Relative thermodynamic stabilities of isomeric alkyl allyl and alkyl (Z)-propenyl ethers,
Tetrahedron, 1993, 49, 11389-11394. [all data]
Holmes and Lossing, 1986
Holmes, J.L.; Lossing, F.P.,
Title unavailable,
Personal communication to S.G. Lias, 1986. [all data]
McAlduff, Caramella, et al., 1978
McAlduff, E.J.; Caramella, P.; Houk, K.N.,
Photoelectron spectra of 3-substituted cyclopentenes. Correlations between ionization potentials and cycloaddition regioselectivity,
J. Am. Chem. Soc., 1978, 100, 105. [all data]
Holmes and Lossing, 1984
Holmes, J.L.; Lossing, F.P.,
Heats of formation of organic radicals from appearance energies,
Int. J. Mass Spectrom. Ion Processes, 1984, 58, 113. [all data]
Zenkevich, 2005
Zenkevich, I.G.,
Experimentally measured retention indices., 2005. [all data]
Notes
Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Gas Chromatography, References
- Symbols used in this document:
AE Appearance energy Tboil Boiling point ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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