Thiophene

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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 as indicated in comments:
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Δfgas218.4kJ/molN/AZaheeruddin and Lodhi, 1991Value computed using ΔfHliquid° value of 183.0 kj/mol from Zaheeruddin and Lodhi, 1991 and ΔvapH° value of 35.4 kj/mol from Hubbard, Scott, et al., 1955.; DRB
Δfgas116.4kJ/molN/ASunner, 1963Value computed using ΔfHliquid° value of 81.0±0.6 kj/mol from Sunner, 1963 and ΔvapH° value of 35.4 kj/mol from Hubbard, Scott, et al., 1955.; DRB
Δfgas115.0 ± 1.0kJ/molCcbHubbard, Scott, et al., 1955see Waddington, Knowlton, et al., 1949; ALS
Δfgas116.7kJ/molN/AMoore, Renquist, et al., 1940Value computed using ΔfHliquid° value of 81.3±2.6 kj/mol from Moore, Renquist, et al., 1940 and ΔvapH° value of 35.4 kj/mol from Hubbard, Scott, et al., 1955.; DRB

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
Δfliquid  CcbZaheeruddin and Lodhi, 1991uncertain value: 182.96 kJ/mol; Author's hf_SO2=-320.5 kJ/mol; ALS
Δfliquid80.96 ± 0.63kJ/molCcrSunner, 1963Correction of Sunner, 1955; ALS
Δfliquid79.6 ± 1.0kJ/molCcbHubbard, Scott, et al., 1955Reanalyzed by Cox and Pilcher, 1970, Original value = 80.33 ± 1.0 kJ/mol; see Waddington, Knowlton, et al., 1949; ALS
Δfliquid81.3 ± 2.6kJ/molCcbMoore, Renquist, et al., 1940Reanalyzed by Cox and Pilcher, 1970, Original value = 81.76 kJ/mol; hf_H2SO4=-135.01; ALS
Quantity Value Units Method Reference Comment
Δcliquid  CcbZaheeruddin and Lodhi, 1991uncertain value: -2649.19 kJ/mol; Author's hf_SO2=-320.5 kJ/mol; ALS
Δcliquid-2828.8kJ/molCcrSunner, 1963Correction of Sunner, 1955; ALS
Δcliquid-2827.6 ± 0.92kJ/molCcbHubbard, Scott, et al., 1955Reanalyzed by Cox and Pilcher, 1970, Original value = -2826.5 ± 0.90 kJ/mol; see Waddington, Knowlton, et al., 1949; ALS
Δcliquid-2829.3 ± 2.5kJ/molCcbMoore, Renquist, et al., 1940Reanalyzed by Cox and Pilcher, 1970, Original value = -2792.4 ± 2.5 kJ/mol; hf_H2SO4=-135.01; ALS
Quantity Value Units Method Reference Comment
liquid181.2J/mol*KN/AFiguiere, Szwarc, et al., 1985DH
liquid181.17J/mol*KN/AWaddington, Knowlton, et al., 1949DH
liquid176.6J/mol*KN/AJacobs and Parks, 1934Details of extrapolation below 90 K not given. Scatter in data for solid introduce uncertainty. Value good to about 4 J/mol*K.; DH

Constant pressure heat capacity of liquid

Cp,liquid (J/mol*K) Temperature (K) Reference Comment
122.40298.14Figuiere, Szwarc, et al., 1985T = 13 to 300 K. Value is unsmoothed experimental datum.; DH
123.85297.45Waddington, Knowlton, et al., 1949T = 11 to 336 K. Value is unsmoothed experimental datum.; DH
123.22289.3Jacobs and Parks, 1934T = 93 to 294 K. Data for solid, 90 to 237 K, not given (table omitted, apparently). 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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Tboil357.3 ± 0.6KAVGN/AAverage of 7 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus234.93KN/AGoates, Ott, et al., 1973Uncertainty assigned by TRC = 0.05 K; TRC
Tfus234.94KN/ATimmermans and Hennaut-Roland, 1959Uncertainty assigned by TRC = 0.1 K; TRC
Tfus233.15KN/ATimmermans and Mattaar, 1921Uncertainty assigned by TRC = 0.4 K; TRC
Quantity Value Units Method Reference Comment
Ttriple235.02KN/AFiguiere, Szwarc, et al., 1985, 2Crystal phase 1 phase; Uncertainty assigned by TRC = 0.05 K; TRC
Ttriple234.900KN/AWaddington, Knowlton, et al., 1949, 2Crystal phase 1 phase; Uncertainty assigned by TRC = 0.08 K; TRC
Ttriple234.95KN/AWaddington, Knowlton, et al., 1949, 2Crystal phase 1 phase; Uncertainty assigned by TRC = 0.06 K; TRC
Ttriple233.7KN/AJacobs and Parks, 1934, 2Uncertainty assigned by TRC = 0.4 K; TRC
Quantity Value Units Method Reference Comment
Tc579.4KN/AMajer and Svoboda, 1985 
Tc579.4KN/ACheng, McCoubrey, et al., 1962Uncertainty assigned by TRC = 0.3 K; Visual (5-cm 2-mm bore tubes) in nitrate-nitrite bath, TE or TH cal. vs NPL thermometer J.C.McCoubrey, A.R.Ubbelohde Trans. Faraday Soc. 1960,56,114; TRC
Tc580.KN/AKobe, Ravicz, et al., 1956Uncertainty assigned by TRC = 2. K; TRC
Quantity Value Units Method Reference Comment
Pc57.00barN/AKobe, Ravicz, et al., 1956Uncertainty assigned by TRC = 0.6894 bar; TRC
Quantity Value Units Method Reference Comment
Vc0.220l/molN/AKobe, Ravicz, et al., 1956Uncertainty assigned by TRC = 0.005 l/mol; TRC
Quantity Value Units Method Reference Comment
Δvap34.79kJ/molN/AMajer and Svoboda, 1985 
Δvap34.6kJ/molN/AReid, 1972AC
Δvap34.7 ± 0.03kJ/molVHubbard, Scott, et al., 1955see Waddington, Knowlton, et al., 1949; ALS
Δvap35.4kJ/molN/AHubbard, Scott, et al., 1955DRB

Enthalpy of vaporization

ΔvapH (kJ/mol) Temperature (K) Method Reference Comment
31.48357.3N/AMajer and Svoboda, 1985 
35.8282.N/ADykyj, Svoboda, et al., 1999Based on data from 267. to 381. K.; AC
34.8348.IEon, Pommier, et al., 1971Based on data from 333. to 373. K.; AC
34.1315.EBWhite, Barnard--Smith, et al., 1952Based on data from 300. to 366. K.; AC
33.7326.N/AWaddington, Knowlton, et al., 1949Based on data from 311. to 393. K.; AC
33.6 ± 0.1319.CWaddington, Knowlton, et al., 1949AC
32.7 ± 0.1336.CWaddington, Knowlton, et al., 1949AC
31.5 ± 0.1357.CWaddington, Knowlton, et al., 1949AC
32.6353.N/AFawcett and Rasmussen, 1945Based on data from 344. to 363. K.; AC
35.270.N/AMilazzo, 1944Based on data from 228. to 289. K.; AC

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
319. to 357.49.560.288579.4Majer 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 373.55.067161790.319-2.805Eon, Pommier, et al., 1971Coefficents calculated by NIST from author's data.
312.21 to 392.944.073581239.578-52.585Waddington, Knowlton, et al., 1949Coefficents calculated by NIST from author's data.

Enthalpy of sublimation

ΔsubH (kJ/mol) Temperature (K) Reference Comment
46.8213.Stephenson and Malanowski, 1987Based on data from 195. to 228. K. See also Milazzo, 1956.; AC
49.203.Milazzo, 1944Based on data from 192. to 213. K.; AC

Enthalpy of fusion

ΔfusH (kJ/mol) Temperature (K) Reference Comment
4.97235.2Domalski and Hearing, 1996See also Figuiere, Szwarc, et al., 1985.; AC

Temperature of phase transition

Ttrs (K) Initial Phase Final Phase Reference Comment
90.76crystaline, V'crystaline, IV'Figuiere, Szwarc, et al., 1984Metastable transition.; DH
139.2crystaline, IV'crystaline, III'Figuiere, Szwarc, et al., 1984Metastable transition.; DH
112.35crystaline, Vcrystaline, IVFiguiere, Szwarc, et al., 1984DH
138.5crystaline, IVcrystaline, IIIFiguiere, Szwarc, et al., 1984DH
170.70crystaline, IIIcrystaline, IIFiguiere, Szwarc, et al., 1984DH
175.03crystaline, IIcrystaline, IFiguiere, Szwarc, et al., 1984DH
235.03crystaline, IliquidFiguiere, Szwarc, et al., 1984DH
111.3crystaline, Vcrystaline, IVAndre, Dworkin, et al., 1982DH
136.8crystaline, IVcrystaline, IIIAndre, Dworkin, et al., 1982DH
170.5crystaline, IIIcrystaline, IIAndre, Dworkin, et al., 1982DH
174.5crystaline, IIcrystaline, IAndre, Dworkin, et al., 1982DH

Enthalpy of phase transition

ΔHtrs (kJ/mol) Temperature (K) Initial Phase Final Phase Reference Comment
0.42844. to 170.crystaline, Vcrystaline, IIIFiguiere, Szwarc, et al., 1985DH
0.8097170.70crystaline, IIIcrystaline, IIFiguiere, Szwarc, et al., 1985DH
1.83637. to 216.crystaline, II'crystaline, IFiguiere, Szwarc, et al., 1985DH
5.040235.02crystaline, IliquidFiguiere, Szwarc, et al., 1985DH
0.6376171.6crystaline, IIcrystaline, IWaddington, Knowlton, et al., 1949Anomalous heat capacity 100 to 150 K. Apparently two second order transitions at about 112, 138 K, with small energies involved.; DH
5.0861234.95crystaline, IliquidWaddington, Knowlton, et al., 1949DH
1.209171.1crystaline, IIcrystaline, IJacobs and Parks, 1934DH
4.966233.7crystaline, IliquidJacobs and Parks, 1934DH

Entropy of phase transition

ΔStrs (J/mol*K) Temperature (K) Initial Phase Final Phase Reference Comment
4.044. to 170.crystaline, Vcrystaline, IIIFiguiere, Szwarc, et al., 1985DH
4.74170.70crystaline, IIIcrystaline, IIFiguiere, Szwarc, et al., 1985DH
15.037. to 216.crystaline, II'crystaline, IFiguiere, Szwarc, et al., 1985DH
21.43235.02crystaline, IliquidFiguiere, Szwarc, et al., 1985DH
3.72171.6crystaline, IIcrystaline, IWaddington, Knowlton, et al., 1949Anomalous; DH
21.65234.95crystaline, IliquidWaddington, Knowlton, et al., 1949DH
7.1171.1crystaline, IIcrystaline, IJacobs and Parks, 1934DH
21.3233.7crystaline, IliquidJacobs and Parks, 1934DH

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


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
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias

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

C4H3S- + Hydrogen cation = Thiophene

By formula: C4H3S- + H+ = C4H4S

Quantity Value Units Method Reference Comment
Δr1595. ± 13.kJ/molG+TSDePuy, Kass, et al., 1988gas phase; Between MeOH, EtOH. D exchange implies anion at C-2.; B
Quantity Value Units Method Reference Comment
Δr1561. ± 13.kJ/molIMRBDePuy, Kass, et al., 1988gas phase; Between MeOH, EtOH. D exchange implies anion at C-2.; B

C4H4S+ + Thiophene = (C4H4S+ • Thiophene)

By formula: C4H4S+ + C4H4S = (C4H4S+ • C4H4S)

Quantity Value Units Method Reference Comment
Δr70.7kJ/molPHPMSHiraoka, Takimoto, et al., 1987gas phase; M
Quantity Value Units Method Reference Comment
Δr96.7J/mol*KPHPMSHiraoka, Takimoto, et al., 1987gas phase; M

(C4H4S+ • Thiophene) + Thiophene = (C4H4S+ • 2Thiophene)

By formula: (C4H4S+ • C4H4S) + C4H4S = (C4H4S+ • 2C4H4S)

Quantity Value Units Method Reference Comment
Δr31.kJ/molPHPMSHiraoka, Takimoto, et al., 1987gas phase; ΔrH<; M

C4H5S+ + Thiophene = (C4H5S+ • Thiophene)

By formula: C4H5S+ + C4H4S = (C4H5S+ • C4H4S)

Quantity Value Units Method Reference Comment
Δr48.1kJ/molPHPMSHiraoka, Takimoto, et al., 1987gas phase; ΔrH<; M

Henry's Law 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: Rolf Sander

Henry's Law constant (water solution)

kH(T) = H exp(d(ln(kH))/d(1/T) ((1/T) - 1/(298.15 K)))
H = Henry's law constant for solubility in water at 298.15 K (mol/(kg*bar))
d(ln(kH))/d(1/T) = Temperature dependence constant (K)

H (mol/(kg*bar)) d(ln(kH))/d(1/T) (K) Method Reference Comment
0.34 QN/A missing citation give several references for the Henry's law constants but don't assign them to specific species.
0.443700.MN/A 

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Zaheeruddin and Lodhi, 1991
Zaheeruddin, M.; Lodhi, Z.H., Enthalpies of formation of some cyclic compounds, Phys. Chem. (Peshawar Pak.), 1991, 10, 111-118. [all data]

Hubbard, Scott, et al., 1955
Hubbard, W.N.; Scott, D.W.; Frow, F.R.; Waddington, G., Thiophene: Heat of combustion and chemical thermodynamic properties, J. Am. Chem. Soc., 1955, 77, 5855-58. [all data]

Sunner, 1963
Sunner, S., Corrected heat of combustion and formation values for a number of organic sulphur compounds, Acta Chem. Scand., 1963, 17, 728-730. [all data]

Waddington, Knowlton, et al., 1949
Waddington, G.; Knowlton, J.W.; Scott, D.W.; Oliver, G.D.; Todd, S.S.; Hubbard, W.N.; Smith, J.C.; Huffman, H.M., Thermodynamic propertie of thiophene, J. Am. Chem. Soc., 1949, 71, 797-808. [all data]

Moore, Renquist, et al., 1940
Moore, G.E.; Renquist, M.L.; Parks, G.S., Thermal data on organic compounds. XX. Modern combustion data for two methylnonanes, methyl ethyl ketone, thiophene and six cycloparaffins, J. Am. Chem. Soc., 1940, 62, 1505-1507. [all data]

Sunner, 1955
Sunner, S., Thermochemical investigations on organic sulfur compounds. V. On the resonance energy of thiolacetic acid, thiourea, thiosemicarbzaide, thiophene and thianthrene, Acta Chem. Scand., 1955, 9, 847-854. [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]

Figuiere, Szwarc, et al., 1985
Figuiere, P.; Szwarc, H.; Oguni, M.; Suga, H., Calorimetric study of thiophene from 13 to 300 K. Emergence of two glassy crystalline states, J. Chem. Thermodynam., 1985, 17, 949-966. [all data]

Jacobs and Parks, 1934
Jacobs, C.J.; Parks, G.S., Thermal data on organic compounds. XIV. Some heat capacity, entropy and free energy data for cyclic substances, J. Am. Chem. Soc., 1934, 56, 1513-1517. [all data]

Goates, Ott, et al., 1973
Goates, J.R.; Ott, J.B.; Reeder, J., Solid + liquid phae equilibria and solid compound formation in hexafluorobenzene + benzene, + pyridine, + furan, and + thiophen, J. Chem. Thermodyn., 1973, 5, 135. [all data]

Timmermans and Hennaut-Roland, 1959
Timmermans, J.; Hennaut-Roland, M., Work of the International Bureau of Physico-Chemical Properties physical constants of twenty organic compounds, J. Chim. Phys. Phys.-Chim. Biol., 1959, 56, 984-1023. [all data]

Timmermans and Mattaar, 1921
Timmermans, J.; Mattaar, J.F., Freezing points of orgainic substances VI. New experimental determinations., Bull. Soc. Chim. Belg., 1921, 30, 213. [all data]

Figuiere, Szwarc, et al., 1985, 2
Figuiere, P.; Szwarc, H.; Oguni, M.; Suga, H., Calorimetric study of thiophene from 13 to 300 K. Emergence of two glassy crystalline states, J. Chem. Thermodyn., 1985, 17, 10, 949, https://doi.org/10.1016/0021-9614(85)90008-4 . [all data]

Waddington, Knowlton, et al., 1949, 2
Waddington, G.; Knowlton, J.W.; Scott, D.W.; Oliver, G.D.; Todd, S.S.; Hubbard, W.N.; Smith, J.C.; Huffman, H.M., Thermodynamic Properties of Thiophene, J. Am. Chem. Soc., 1949, 71, 797. [all data]

Jacobs and Parks, 1934, 2
Jacobs, C.J.; Parks, G.S., Thermal data on organic compounds. XIV. Some heat capacity, entropy and free energy data for cyclic substances, J. Am. Chem. Soc., 1934, 56, 1513-17. [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]

Cheng, McCoubrey, et al., 1962
Cheng, D.C.H.; McCoubrey, J.C.; Phillips, D.G., Critical Temperatures of Some Organic Cyclic Compounds, Trans. Faraday Soc., 1962, 58, 224. [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]

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]

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]

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]

Fawcett and Rasmussen, 1945
Fawcett, Frank S.; Rasmussen, Herbert E., Physical Properties of Thiophene 1, J. Am. Chem. Soc., 1945, 67, 10, 1705-1709, https://doi.org/10.1021/ja01226a026 . [all data]

Milazzo, 1944
Milazzo, G., Gazz. Chim. Ital., 1944, 74, 58. [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]

Milazzo, 1956
Milazzo, G., Ann. Chim. (Rome), 1956, 46, 1105. [all data]

Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D., Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III, J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985 . [all data]

Figuiere, Szwarc, et al., 1984
Figuiere, P.; Szwarc, H.; Oguni, M.; Suga, H., Crystalline thiophene - calorimetric evidence for a glassy crystalline state in both phase sequences, J. Phys., Lett., 1984, 45(24), L1167-L1173. [all data]

Andre, Dworkin, et al., 1982
Andre, D.; Dworkin, A.; Figuiere, P.; Fuchs, A.H.; Szwarc, H., Heat capacity of stable and metastable phases of crystalline thiophene, C. R. Seances Acad. Sci., Ser. 2, 1982, 295, 145-147. [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]

Hiraoka, Takimoto, et al., 1987
Hiraoka, K.; Takimoto, H.; Yamabe, S., Stabilities and Structures in Cluster Ions of Five-Membered Heterocyclic Compounds Containing O, N and S Atoms, J. Am. Chem. Soc., 1987, 109, 24, 7346, https://doi.org/10.1021/ja00258a018 . [all data]


Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, References