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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
Deltafgas218.4kJ/molN/AZaheeruddin and Lodhi, 1991Value computed using «DELTA»fHliquid° value of 183.0 kj/mol from Zaheeruddin and Lodhi, 1991 and «DELTA»vapH° value of 35.4 kj/mol from Hubbard, Scott, et al., 1955.; DRB
Deltafgas116.4kJ/molN/ASunner, 1963Value computed using «DELTA»fHliquid° value of 81.0±0.6 kj/mol from Sunner, 1963 and «DELTA»vapH° value of 35.4 kj/mol from Hubbard, Scott, et al., 1955.; DRB
Deltafgas115.0 ± 1.0kJ/molCcbHubbard, Scott, et al., 1955see Waddington, Knowlton, et al., 1949; ALS
Deltafgas116.7kJ/molN/AMoore, Renquist, et al., 1940Value computed using «DELTA»fHliquid° value of 81.3±2.6 kj/mol from Moore, Renquist, et al., 1940 and «DELTA»vapH° 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
Deltafliquid  CcbZaheeruddin and Lodhi, 1991uncertain value: 182.96 kJ/mol; Author's hf_SO2=-320.5 kJ/mol; ALS
Deltafliquid80.96 ± 0.63kJ/molCcrSunner, 1963Correction of Sunner, 1955; ALS
Deltafliquid79.6 ± 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
Deltafliquid81.3 ± 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
Deltacliquid  CcbZaheeruddin and Lodhi, 1991uncertain value: -2649.19 kJ/mol; Author's hf_SO2=-320.5 kJ/mol; ALS
Deltacliquid-2828.8kJ/molCcrSunner, 1963Correction of Sunner, 1955; ALS
Deltacliquid-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
Deltacliquid-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

Reaction thermochemistry data

Go To: Top, Gas phase thermochemistry data, Condensed phase 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 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
Deltar1595. ± 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
Deltar1561. ± 13.kJ/molIMRBDePuy, Kass, et al., 1988gas phase; Between MeOH, EtOH. D exchange implies anion at C-2.; B

C4H4S+ + Thiophene = (C4H4S+ bullet Thiophene)

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

Quantity Value Units Method Reference Comment
Deltar70.7kJ/molPHPMSHiraoka, Takimoto, et al., 1987gas phase; M
Quantity Value Units Method Reference Comment
Deltar96.7J/mol*KPHPMSHiraoka, Takimoto, et al., 1987gas phase; M

(C4H4S+ bullet Thiophene) + Thiophene = (C4H4S+ bullet 2Thiophene)

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

Quantity Value Units Method Reference Comment
Deltar31.kJ/molPHPMSHiraoka, Takimoto, et al., 1987gas phase; «DELTA»rH<; M

C4H5S+ + Thiophene = (C4H5S+ bullet Thiophene)

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

Quantity Value Units Method Reference Comment
Deltar48.1kJ/molPHPMSHiraoka, Takimoto, et al., 1987gas phase; «DELTA»rH<; M

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry 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.

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]

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, Reaction thermochemistry data, References