Thiophene, 2-methyl-
- Formula: C5H6S
- Molecular weight: 98.166
- IUPAC Standard InChIKey: XQQBUAPQHNYYRS-UHFFFAOYSA-N
- CAS Registry Number: 554-14-3
- 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: 2-Methylthiophene; 2-Methylthiacyclopentadiene; 2-methylthiacyclopentadiene (2-methylthiophene)
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | 84.35 ± 0.92 | kJ/mol | Ccr | Pennington, Finke, et al., 1956 |
Condensed 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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°liquid | 44.60 ± 0.92 | kJ/mol | Ccr | Pennington, Finke, et al., 1956 | Reanalyzed by Cox and Pilcher, 1970, Original value = 45.44 ± 0.88 kJ/mol; ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -3472.0 ± 0.75 | kJ/mol | Ccr | Pennington, Finke, et al., 1956 | Reanalyzed by Cox and Pilcher, 1970, Original value = -3471.3 ± 0.75 kJ/mol; ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 218.49 | J/mol*K | N/A | Pennington, Finke, et al., 1956 | DH |
Constant pressure heat capacity of liquid
Cp,liquid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
149.83 | 298.15 | Pennington, Finke, et al., 1956 | T = 12 to 340 K.; DH |
Constant pressure heat capacity of solid
Cp,solid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
97.91 | 199.70 | Carlson and Westrum, 1968 | glass phase; T = 110 to 200 K. Value is unsmoothed experimental datum.; DH |
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
AC - William E. Acree, Jr., James S. Chickos
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 385.8 | K | N/A | Weast and Grasselli, 1989 | BS |
Tboil | 385.7 | K | N/A | Majer and Svoboda, 1985 | |
Tboil | 385.15 | K | N/A | Levi and Nicholls, 1958 | Uncertainty assigned by TRC = 1.5 K; TRC |
Tboil | 386. | K | N/A | Haines, Helm, et al., 1956 | Uncertainty assigned by TRC = 0.3 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 209.77 | K | N/A | Haines, Helm, et al., 1956 | Uncertainty assigned by TRC = 0.06 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 209.79 | K | N/A | Pennington, Finke, et al., 1956, 2 | Uncertainty assigned by TRC = 0.05 K; extrapolate 1/f to zero; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 606.2 | K | N/A | Majer and Svoboda, 1985 | |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 38.91 | kJ/mol | N/A | Majer and Svoboda, 1985 | |
ΔvapH° | 38.7 | kJ/mol | N/A | Reid, 1972 | AC |
ΔvapH° | 39.8 | kJ/mol | N/A | Pennington, Finke, et al., 1956 | DRB |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
33.9 | 385.7 | N/A | Majer and Svoboda, 1985 | |
37.2 | 339. | A,EB | Stephenson and Malanowski, 1987 | Based on data from 324. to 391. K. See also White, Barnard--Smith, et al., 1952 and Dykyj, Svoboda, et al., 1999.; AC |
36.8 | 348. | I | Eon, Pommier, et al., 1971 | Based on data from 333. to 373. K. See also Boublik, Fried, et al., 1984.; AC |
38.9 | 343. | V | Pennington, Finke, et al., 1956 | ALS |
Enthalpy of vaporization
ΔvapH =
A exp(-βTr) (1 − Tr)β
ΔvapH =
Enthalpy of vaporization (at saturation pressure)
(kJ/mol)
Tr = reduced temperature (T / Tc)
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Temperature (K) | A (kJ/mol) | β | Tc (K) | Reference | Comment |
---|---|---|---|---|---|
344. to 386. | 54.25 | 0.2853 | 606.2 | Majer and Svoboda, 1985 |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
333.4 to 373.5 | 4.84344 | 1812.35 | -10.276 | Eon, Pommier, et al., 1971 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
11.142 | 207.79 | Pennington, Finke, et al., 1956 | DH |
9.47 | 207.8 | Pennington, Finke, et al., 1956 | AC |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
53.62 | 207.79 | Pennington, Finke, et al., 1956 | DH |
Reaction thermochemistry data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, 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 compiled by: John E. Bartmess
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
C5H5S- + =
By formula: C5H5S- + H+ = C5H6S
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1589. ± 13. | kJ/mol | G+TS | DePuy, Kass, et al., 1988 | gas phase; Acid: 2-methylthiophene. Between MeOH, EtOH. |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1561. ± 13. | kJ/mol | IMRB | DePuy, Kass, et al., 1988 | gas phase; Acid: 2-methylthiophene. Between MeOH, EtOH. |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Pennington, Finke, et al., 1956
Pennington, R.E.; Finke, H.L.; Hubbard, W.N.; Messerly, J.F.; Frow, F.R.; Hossenlopp, I.A.; Waddington, G.,
The chemical thermodynamic properties of 2-methylthiophene,
J. Am. Chem. Soc., 1956, 78, 2055-2060. [all data]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]
Carlson and Westrum, 1968
Carlson, H.G.; Westrum, E.F., Jr.,
Thermal study of the glass-type transformation of 2-methylthiophene,
J. Chem. Eng. Data, 1968, 13, 273-274. [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]
Levi and Nicholls, 1958
Levi, L.; Nicholls, R.V.V.,
Formation of Styrene by Pyrolysis of Aromatic Heterocyclic Aldehyde- Aliphatic Acid Anhydride Mixtures on Morden Bentonite,
Ind. Eng. Chem., 1958, 50, 1005. [all data]
Haines, Helm, et al., 1956
Haines, W.E.; Helm, R.V.; Cook, G.L.; Ball, J.S.,
Purification and Properties of Organic Sulfur Compounds,
J. Phys. Chem., 1956, 60, 549-55. [all data]
Pennington, Finke, et al., 1956, 2
Pennington, R.E.; Finke, H.L.; Hubbard, W.N.; Messerly, J.F.; Frow, F.R.; Hossenlopp, I.A.; Waddington, G.,
The Chemical Thermodynamic Properties of 2-Methylthiophene,
J. Am. Chem. Soc., 1956, 78, 2055-60. [all data]
Reid, 1972
Reid, Robert C.,
Handbook on vapor pressure and heats of vaporization of hydrocarbons and related compounds, R. C. Wilhort and B. J. Zwolinski, Texas A Research Foundation. College Station, Texas(1971). 329 pages.$10.00,
AIChE J., 1972, 18, 6, 1278-1278, https://doi.org/10.1002/aic.690180637
. [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]
White, Barnard--Smith, et al., 1952
White, P.T.; Barnard--Smith, D.G.; Fidler, F.A.,
Vapor Pressure--Temperature Relationships of Sulfur Compounds Related to Petroleum,
Ind. Eng. Chem., 1952, 44, 6, 1430-1438, https://doi.org/10.1021/ie50510a064
. [all data]
Dykyj, Svoboda, et al., 1999
Dykyj, J.; Svoboda, J.; Wilhoit, R.C.; Frenkel, M.L.; Hall, K.R.,
Vapor Pressure of Chemicals: Part A. Vapor Pressure and Antoine Constants for Hydrocarbons and Sulfur, Selenium, Tellurium and Hydrogen Containing Organic Compounds, Springer, Berlin, 1999, 373. [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]
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, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, References
- Symbols used in this document:
Cp,liquid Constant pressure heat capacity of liquid Cp,solid Constant pressure heat capacity of solid S°liquid Entropy of liquid at standard conditions Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point Ttriple Triple point temperature ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions 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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