Thiophene
- Formula: C4H4S
- Molecular weight: 84.140
- IUPAC Standard InChIKey: YTPLMLYBLZKORZ-UHFFFAOYSA-N
- CAS Registry Number: 110-02-1
- 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: Thiacyclopentadiene; CP 34; Furan, thio-; Huile HSO; Huile H50; Thiaphene; Thiofuram; Thiofuran; Thiofurfuran; Thiole; Thiophen; Thiotetrole; Divinylene sulfide; USAF EK-1860; Thiofen; UN 2414; Hopkin's lactic acid reagent; NSC 405073
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Gas phase thermochemistry data
Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, 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:
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | 52.20 | kcal/mol | N/A | Zaheeruddin and Lodhi, 1991 | Value 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 |
ΔfH°gas | 27.82 | kcal/mol | N/A | Sunner, 1963 | Value 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 |
ΔfH°gas | 27.49 ± 0.24 | kcal/mol | Ccb | Hubbard, Scott, et al., 1955 | see Waddington, Knowlton, et al., 1949; ALS |
ΔfH°gas | 27.89 | kcal/mol | N/A | Moore, Renquist, et al., 1940 | Value 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 |
Reaction thermochemistry data
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, 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- + =
By formula: C4H3S- + H+ = C4H4S
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 381.2 ± 3.1 | kcal/mol | G+TS | DePuy, Kass, et al., 1988 | gas phase; Between MeOH, EtOH. D exchange implies anion at C-2.; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 373.0 ± 3.0 | kcal/mol | IMRB | DePuy, Kass, et al., 1988 | gas phase; Between MeOH, EtOH. D exchange implies anion at C-2.; B |
By formula: C4H4S+ + C4H4S = (C4H4S+ • C4H4S)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 16.9 | kcal/mol | PHPMS | Hiraoka, Takimoto, et al., 1987 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 23.1 | cal/mol*K | PHPMS | Hiraoka, Takimoto, et al., 1987 | gas phase; M |
By formula: (C4H4S+ • C4H4S) + C4H4S = (C4H4S+ • 2C4H4S)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 7.5 | kcal/mol | PHPMS | Hiraoka, Takimoto, et al., 1987 | gas phase; ΔrH<; M |
By formula: C4H5S+ + C4H4S = (C4H5S+ • C4H4S)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 11.5 | kcal/mol | PHPMS | Hiraoka, Takimoto, et al., 1987 | gas phase; ΔrH<; M |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Ion clustering data, IR Spectrum, 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
LL - Sharon G. Lias and Joel F. Liebman
View reactions leading to C4H4S+ (ion structure unspecified)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 8.86 ± 0.02 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 194.8 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 187.5 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.85 | PE | Klasinc, Sabljic, et al., 1982 | LBLHLM |
8.85 | PE | Galasso, Klasinc, et al., 1981 | LLK |
9.0 ± 0.1 | CEMS | Tedder and Vidaud, 1980 | LLK |
8.87 ± 0.01 | PE | Butler and Baer, 1980 | LLK |
~8.8 | EI | Van Veen, 1976 | LLK |
8.80 ± 0.05 | EI | Thorstad and Undheim, 1974 | LLK |
8.90 | PE | Clark, Gleiter, et al., 1973 | LLK |
9.05 | CTS | Aloisi and Pignataro, 1973 | LLK |
8.874 ± 0.005 | S | DiLonardo, Galloni, et al., 1972 | LLK |
9.12 ± 0.05 | EI | Linda, Marino, et al., 1971 | LLK |
8.87 ± 0.01 | PE | Derrick, Asbrink, et al., 1971 | LLK |
8.86 ± 0.01 | PI | Potapov and Bazhenov, 1970 | RDSH |
8.80 ± 0.05 | PE | Baker, Betteridge, et al., 1970 | RDSH |
8.87 ± 0.05 | PE | Eland, 1969 | RDSH |
8.860 ± 0.005 | PI | Watanabe, Nakayama, et al., 1962 | RDSH |
8.95 ± 0.02 | S | Price and Walsh, 1941 | RDSH |
8.85 | PE | Bajic, Humski, et al., 1985 | Vertical value; LBLHLM |
8.90 | PE | Bock and Roth, 1983 | Vertical value; LBLHLM |
8.90 | PE | Mellink and Janssen, 1978 | Vertical value; LLK |
8.85 | PE | Bozic, Humski, et al., 1977 | Vertical value; LLK |
8.87 | PE | Schafer, Schweig, et al., 1973 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
CHS+ | 13.0 ± 0.2 | C3H3 | CEMS | Tedder and Vidaud, 1980 | LLK |
CHS+ | 13.19 ± 0.04 | C3H3 | PE | Butler and Baer, 1980 | LLK |
CHS+ | 13.0 ± 0.2 | ? | EI | Khvostenko, 1962 | RDSH |
C2H2S+ | 12.5 ± 0.2 | C2H2 | CEMS | Tedder and Vidaud, 1980 | LLK |
C2H2S+ | 12.1 ± 0.1 | C2H2 | PE | Butler and Baer, 1980 | LLK |
C2H2S+ | 10.8 ± 0.2 | ? | EI | Khvostenko, 1962 | RDSH |
C3HS+ | 12.95 ± 0.05 | CH3 | PE | Butler and Baer, 1980 | LLK |
C3H3+ | 13.0 ± 0.2 | CHS | CEMS | Tedder and Vidaud, 1980 | LLK |
C3H3+ | 13.06 ± 0.05 | CHS | PE | Butler and Baer, 1980 | LLK |
C3H3+ | 12.8 ± 0.2 | ? | EI | Khvostenko, 1962 | RDSH |
C4H3S+ | 12.93 ± 0.07 | H | PE | Butler and Baer, 1980 | LLK |
S+ | 20.0 ± 0.5 | ? | EI | Stepanov, Perov, et al., 1988 | LL |
De-protonation reactions
C4H3S- + =
By formula: C4H3S- + H+ = C4H4S
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 381.2 ± 3.1 | kcal/mol | G+TS | DePuy, Kass, et al., 1988 | gas phase; Between MeOH, EtOH. D exchange implies anion at C-2.; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 373.0 ± 3.0 | kcal/mol | IMRB | DePuy, Kass, et al., 1988 | gas phase; Between MeOH, EtOH. D exchange implies anion at C-2.; B |
Ion clustering data
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, 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: 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. Searches may be limited to ion clustering reactions. A general reaction search form is also available.
Clustering reactions
By formula: C4H4S+ + C4H4S = (C4H4S+ • C4H4S)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 16.9 | kcal/mol | PHPMS | Hiraoka, Takimoto, et al., 1987 | gas phase |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 23.1 | cal/mol*K | PHPMS | Hiraoka, Takimoto, et al., 1987 | gas phase |
By formula: (C4H4S+ • C4H4S) + C4H4S = (C4H4S+ • 2C4H4S)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 7.5 | kcal/mol | PHPMS | Hiraoka, Takimoto, et al., 1987 | gas phase; ΔrH< |
By formula: C4H5S+ + C4H4S = (C4H5S+ • C4H4S)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 11.5 | kcal/mol | PHPMS | Hiraoka, Takimoto, et al., 1987 | gas phase; ΔrH< |
IR Spectrum
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, References, Notes
Data compiled by: Coblentz Society, Inc.
References
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, 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]
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]
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]
Klasinc, Sabljic, et al., 1982
Klasinc, L.; Sabljic, A.; Kluge, G.; Rieger, J.; Scholz, M.,
Chemistry of excited states. Part 13. Assignment of lowest .PI.-ionizations in photoelectron spectra of thiophen, furan, and pyrrole,
J. Chem. Soc. Perkin Trans. 2, 1982, 539. [all data]
Galasso, Klasinc, et al., 1981
Galasso, V.; Klasinc, L.; Sabluic, A.; Trinajstic, N.; Pappalardo, G.C.; Steglich, W.,
Conformation and photoelectron spectra of 2-(2-Furyl)pyrrole and 2-(2-tThienyl)pyrrole,
J. Chem. Soc. Perkin Trans. 2, 1981, 127. [all data]
Tedder and Vidaud, 1980
Tedder, J.M.; Vidaud, P.H.,
Charge exchange mass spectra of thiophene, pyrrole and furan,
J. Chem. Soc. Faraday Trans. 2, 1980, 76, 1516. [all data]
Butler and Baer, 1980
Butler, J.J.; Baer, T.,
Thermochemistry and dissociation dynamics of state-selected C4H4X ions. 1. Thiophene,
J. Am. Chem. Soc., 1980, 102, 6764. [all data]
Van Veen, 1976
Van Veen, E.H.,
Triplet π-π* transitions in thiophene, furan and pyrrole by low-energy electron-impact spectroscopy,
Chem. Phys. Lett., 1976, 41, 535. [all data]
Thorstad and Undheim, 1974
Thorstad, O.; Undheim, K.,
Mass spectrometry of onium compounds. XXIV. Ionisation potential in structure analysis of pyridodiazo-oxides,
Chem. Scr., 1974, 6, 222. [all data]
Clark, Gleiter, et al., 1973
Clark, P.A.; Gleiter, R.; Heilbronner, E.,
Photoelectron spectra of planar sulfur J. Heterocycl. Chem.,
Tetrahedron, 1973, 29, 3085. [all data]
Aloisi and Pignataro, 1973
Aloisi, G.G.; Pignataro, S.,
Molecular complexes of substituted thiophens with σ and π acceptors,
J. Chem. Soc. Faraday Trans. 1, 1973, 69, 534. [all data]
DiLonardo, Galloni, et al., 1972
DiLonardo, G.; Galloni, G.; Trombetti, A.; Zauli, C.,
Electronic spectrum of thiophen and some deuterated thiophens,
J. Chem. Soc. Faraday Trans., 1972, 68, 2009. [all data]
Linda, Marino, et al., 1971
Linda, P.; Marino, G.; Pignataro, S.,
A comparison of sensitivities to substituent effects of five- membered heteroaromatic rings in gas phase ionization,
J. Chem. Soc. B, 1971, 1585. [all data]
Derrick, Asbrink, et al., 1971
Derrick, P.J.; Asbrink, L.; Edqvist, O.; Lindholm, E.,
Photoelectron-spectroscopical study of the vibrations of furan, thiophene, pyrrole and cyclopentadiene,
Spectrochim. Acta, 1971, 27A, 2525. [all data]
Potapov and Bazhenov, 1970
Potapov, V.K.; Bazhenov, B.A.,
The photionization of pyrrole, furan, and thiophene,
High Energy Chem., 1970, 505, In original 553. [all data]
Baker, Betteridge, et al., 1970
Baker, A.D.; Betteridge, D.; Kemp, N.R.; Kirby, R.E.,
Application of photoelectron spectrometry to pesticide analysis. Photoelectron spectra of fivemembered heterocycles and related molecules,
Anal. Chem., 1970, 42, 1064. [all data]
Eland, 1969
Eland, J.H.D.,
Photoelectron spectra of conjugated hydrocarbons and heteromolecules,
Intern. J. Mass Spectrom. Ion Phys., 1969, 2, 471. [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]
Price and Walsh, 1941
Price, W.C.; Walsh, A.D.,
The absorption spectra of the cyclic dienes in the vacuum ultra-violet,
Proc. Roy. Soc. (London), 1941, A179, 201. [all data]
Bajic, Humski, et al., 1985
Bajic, M.; Humski, K.; Klasinc, L.; Ruscic, B.,
Substitution effects on electronic structure of thiophene,
Z. Naturforsch. B:, 1985, 40, 1214. [all data]
Bock and Roth, 1983
Bock, H.; Roth, B.,
Radical ions. 49. Redox reactions of some thiophene derivatives,
Phosphorus Sulfur, 1983, 14, 211. [all data]
Mellink and Janssen, 1978
Mellink, W.A.; Janssen, M.J.,
Photoelectron spectra of aromatic sulphides and sulphones,
J. Chem. Res. Synop., 1978, 422. [all data]
Bozic, Humski, et al., 1977
Bozic, Z.; Humski, K.; Cvitas, T.; Klasinc, L.,
Photoelectron spectra of bromo- and iodo- thiophens,
J. Chem. Soc. Perkin Trans. 2, 1977, 1413. [all data]
Schafer, Schweig, et al., 1973
Schafer, W.; Schweig, A.; Gronowitz, S.; Taticchi, A.; Fringuelli, F.,
Reversal in the sequence of two highest occupied molecular orbitals in the series thiophen, selenophen, and tellurophen,
J. Chem. Soc. Chem. Commun., 1973, 541. [all data]
Khvostenko, 1962
Khvostenko, V.I.,
Ionisation of thiophen and some of its derivatives by electron impact,
Zh. Fiz. Khim., 1962, 36, 384, In original 197. [all data]
Stepanov, Perov, et al., 1988
Stepanov, A.N.; Perov, A.A.; Kabanov, S.P.; Simonov, A.P.,
Formation of long-lived, highly excited atoms during dissociative excitation of CH3CN, CH3CH2OH, CH3COOH, HCOOH, and C4H4S molecules on electron impact,
Russ. J. Phys. Chem., 1988, 22, 81. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, References
- Symbols used in this document:
AE Appearance energy IE (evaluated) Recommended ionization energy ΔfH°gas Enthalpy of formation of gas at standard conditions ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔrS° Entropy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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