Furan, 2-methyl-
- Formula: C5H6O
- Molecular weight: 82.1005
- IUPAC Standard InChIKey: VQKFNUFAXTZWDK-UHFFFAOYSA-N
- CAS Registry Number: 534-22-5
- 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: α-Methylfuran; Silvan; Sylvan; 2-Methylfuran; 5-Methylfuran; Methylfuran; UN 2301; 2-Methylfurane
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Phase change data
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 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
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 337. ± 1. | K | AVG | N/A | Average of 10 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 181.9 | K | N/A | Carlson and Westrum, 1965 | Uncertainty assigned by TRC = 0.1 K; TRC |
Ttriple | 181.90 | K | N/A | Carlson, 1962 | Uncertainty assigned by TRC = 0.2 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 528. | K | N/A | Kobe, Ravicz, et al., 1956 | Uncertainty assigned by TRC = 2. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 47.20 | bar | N/A | Kobe, Ravicz, et al., 1956 | Uncertainty assigned by TRC = 1.034 bar; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Vc | 0.247 | l/mol | N/A | Kobe, Ravicz, et al., 1956 | Uncertainty assigned by TRC = 0.005 l/mol; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 32.2 | kJ/mol | N/A | Moiseev and Antonova, 1970 | Based on data from 215. to 360. K.; AC |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
32.4 | 304. | N/A | Loras, Aucejo, et al., 2002 | Based on data from 289. to 337. K.; AC |
34.4 | 266. | A | Stephenson and Malanowski, 1987 | Based on data from 251. to 338. K.; AC |
31.5 | 324. | N/A | Krevor and Prausnitz, 1986 | Based on data from 309. to 339. K.; AC |
32.5 | 295. | N/A | Dykyj, 1972 | Based on data from 288. to 303. K.; AC |
30.9 | 348. | N/A | Eon, Pommier, et al., 1971 | Based on data from 333. to 373. K. See also Boublik, Fried, et al., 1984.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)
View plot Requires a JavaScript / HTML 5 canvas capable browser.
Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
333.4 to 373.5 | 4.81528 | 1643.082 | 3.234 | Eon, Pommier, et al., 1971 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
8.552 | 181.90 | Carlson and Westrum, 1965, 2 | DH |
8.55 | 181.9 | Carlson and Westrum, 1965, 2 | AC |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
47.01 | 181.90 | Carlson and Westrum, 1965, 2 | DH |
Gas phase ion energetics data
Go To: Top, Phase change data, 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:
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
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 8.38 ± 0.01 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 865.9 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 833.5 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.38 | PE | Veszpremi, Nyulaszi, et al., 1987 | LBLHLM |
8.57 | EI | Spilker and Grutzmacher, 1986 | LBLHLM |
8.38 | PE | Kobayashi, Kubota, et al., 1982 | LBLHLM |
8.39 ± 0.01 | EQ | Lias and Ausloos, 1978 | LLK |
8.39 ± 0.01 | PI | Watanabe, Nakayama, et al., 1962 | RDSH |
8.31 ± 0.09 | EI | Varsel, Morrell, et al., 1960 | RDSH |
8.37 | PE | Zykov, Erchak, et al., 1983 | Vertical value; LBLHLM |
8.54 | PE | Colonna, Distefano, et al., 1979 | Vertical value; LLK |
8.37 ± 0.05 | PE | Fringuelli, Marino, et al., 1976 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C5H5O+ | 10.65 | H | EI | Spilker and Grutzmacher, 1986 | LBLHLM |
De-protonation reactions
C5H5O- + =
By formula: C5H5O- + H+ = C5H6O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1606. ± 13. | kJ/mol | G+TS | DePuy, Kass, et al., 1988 | gas phase; Anion of 2-methylfuran. Order: H2O<furan<2-Me-furan<MeOH.; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1577. ± 13. | kJ/mol | IMRB | DePuy, Kass, et al., 1988 | gas phase; Anion of 2-methylfuran. Order: H2O<furan<2-Me-furan<MeOH.; B |
References
Go To: Top, Phase change data, Gas phase ion energetics data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Carlson and Westrum, 1965
Carlson, H.G.; Westrum, E.F., Jr.,
2-Methylfuran-Heat Capacity and Thermodynamic Properties from 5°to 310° K.,
J. Chem. Eng. Data, 1965, 10, 2, 134, https://doi.org/10.1021/je60025a018
. [all data]
Carlson, 1962
Carlson,
, Ph.D. Thesis, Univ. Mich., Ann Arbor, MI, 1962. [all data]
Kobe, Ravicz, et al., 1956
Kobe, K.A.; Ravicz, A.E.; Vohra, S.P.,
Critical Properties and Vapor Pressures of Some Ethers and Heterocyclic Compounds,
J. Chem. Eng. Data, 1956, 1, 50. [all data]
Moiseev and Antonova, 1970
Moiseev, V.D.; Antonova, N.D.,
Zh. Fiz. Khim., 1970, 44, 11, 2912. [all data]
Loras, Aucejo, et al., 2002
Loras, Sonia; Aucejo, Antonio; Montón, Juan B.; Wisniak, Jaime; Segura, Hugo,
Phase Equilibria for 1,1,1,2,3,4,4,5,5,5-Decafluoropentane + 2-Methylfuran, 2-Methylfuran + Oxolane, and 1,1,1,2,3,4,4,5,5,5- Decafluoropentane + 2-Methylfuran + Oxolane at 35 kPa,
J. Chem. Eng. Data, 2002, 47, 5, 1256-1262, https://doi.org/10.1021/je0255325
. [all data]
Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw,
Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2
. [all data]
Krevor and Prausnitz, 1986
Krevor, David H.; Prausnitz, John M.,
Vapor-liquid equilibria for model mixtures of coal-derived liquids. 1. Binary systems with 2-methylfuran,
J. Chem. Eng. Data, 1986, 31, 3, 349-353, https://doi.org/10.1021/je00045a027
. [all data]
Dykyj, 1972
Dykyj, J.,
Petrochemia, 1972, 12, 1, 13. [all data]
Eon, Pommier, et al., 1971
Eon, C.; Pommier, C.; Guiochon, G.,
Vapor pressures and second virial coefficients of some five-membered heterocyclic derivatives,
J. Chem. Eng. Data, 1971, 16, 4, 408-410, https://doi.org/10.1021/je60051a008
. [all data]
Boublik, Fried, et al., 1984
Boublik, T.; Fried, V.; Hala, E.,
The Vapour Pressures of Pure Substances: Selected Values of the Temperature Dependence of the Vapour Pressures of Some Pure Substances in the Normal and Low Pressure Region, 2nd ed., Elsevier, New York, 1984, 972. [all data]
Carlson and Westrum, 1965, 2
Carlson, H.G.; Westrum, E.F., Jr.,
2-Methylfuran. Heat capacity and thermodynamic properties from 5 to 310 K,
J. Chem. Eng. Data, 1965, 10, 134-135. [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]
Veszpremi, Nyulaszi, et al., 1987
Veszpremi, T.; Nyulaszi, L.; Nagy, J.,
Ultraviolet photoelectron spectroscopy and quantum-mechanical study of alkyl- and trimethylsilyl-furanes,
J. Organomet. Chem., 1987, 331, 175. [all data]
Spilker and Grutzmacher, 1986
Spilker, R.; Grutzmacher, H.-F.,
Isomerization and fragmentation of methylfuran ions and pyran ions in the gas phase,
Org. Mass Spectrom., 1986, 21, 459. [all data]
Kobayashi, Kubota, et al., 1982
Kobayashi, T.; Kubota, T.; Ezumi, K.; Utsunomiya, C.,
Photoelectron angular distribution study of some isoxazoles combined with perturbation theoretic approach,
Bull. Chem. Soc. Jpn., 1982, 55, 3915. [all data]
Lias and Ausloos, 1978
Lias, S.G.; Ausloos, P.J.,
eIonization energies of organic compounds by equilibrium measurements,
J. Am. Chem. Soc., 1978, 100, 6027. [all data]
Watanabe, Nakayama, et al., 1962
Watanabe, K.; Nakayama, T.; Mottl, J.,
Ionization potentials of some molecules,
J. Quant. Spectry. Radiative Transfer, 1962, 2, 369. [all data]
Varsel, Morrell, et al., 1960
Varsel, C.J.; Morrell, F.A.; Resnik, F.E.; Powell, W.A.,
Qualitative and quantitative analysis of organic compounds. Use of low-voltage mass spectrometry,
Anal. Chem., 1960, 32, 182. [all data]
Zykov, Erchak, et al., 1983
Zykov, B.G.; Erchak, N.P.; Khvostenko, V.I.; Lukevits, E.; Matorykina, V.F.; Asfandiarov, N.L.,
Photoelectron spectra of furylsilanes and their carbon analogs,
J. Organomet. Chem., 1983, 253, 301. [all data]
Colonna, Distefano, et al., 1979
Colonna, F.P.; Distefano, G.; Guerra, M.; Jones, D.; Modelli, A.,
Furyl- and thienyl-mercury derivatives studied by means of ultraviolet photoelectron spectroscopy. Evidence for the participation in bonding of the vacant 6p π orbitals of mercury in bis-2-furyl-bis-2-thienylmercury,
J. Chem. Soc. Dalton Trans., 1979, 2037. [all data]
Fringuelli, Marino, et al., 1976
Fringuelli, F.; Marino, G.; Taticchi, A.; Distefano, G.; Colonna, F.P.; Pignataro, S.,
Photoelectron spectra of the α-substituted derivatives of furan, thiophen, selenophen, and tellurophen. A comparative study of the molecular orbital energies,
J. Chem. Soc. Perkin Trans. 2, 1976, 276. [all data]
DePuy, Kass, et al., 1988
DePuy, C.H.; Kass, S.R.; Bean, G.P.,
Formation and Reactions of Heteroaromatic Anions in the Gas Phase,
J. Org. Chem., 1988, 53, 19, 4427, https://doi.org/10.1021/jo00254a001
. [all data]
Notes
Go To: Top, Phase change data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy IE (evaluated) Recommended ionization energy Pc Critical pressure Tboil Boiling point Tc Critical temperature Ttriple Triple point temperature Vc Critical volume ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions 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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