Thiophene

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Reaction thermochemistry 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:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias

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Individual Reactions

C4H3S- + Hydrogen cation = Thiophene

By formula: C4H3S- + H+ = C4H4S

Quantity Value Units Method Reference Comment
Δr381.2 ± 3.1kcal/molG+TSDePuy, Kass, et al., 1988gas phase; Between MeOH, EtOH. D exchange implies anion at C-2.; B
Quantity Value Units Method Reference Comment
Δr373.0 ± 3.0kcal/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
Δr16.9kcal/molPHPMSHiraoka, Takimoto, et al., 1987gas phase; M
Quantity Value Units Method Reference Comment
Δr23.1cal/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
Δr7.5kcal/molPHPMSHiraoka, Takimoto, et al., 1987gas phase; ΔrH<; M

C4H5S+ + Thiophene = (C4H5S+ • Thiophene)

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

Quantity Value Units Method Reference Comment
Δr11.5kcal/molPHPMSHiraoka, Takimoto, et al., 1987gas phase; ΔrH<; M

Gas phase ion energetics data

Go To: Top, 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 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 ± 0.02eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)194.8kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity187.5kcal/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
8.85PEKlasinc, Sabljic, et al., 1982LBLHLM
8.85PEGalasso, Klasinc, et al., 1981LLK
9.0 ± 0.1CEMSTedder and Vidaud, 1980LLK
8.87 ± 0.01PEButler and Baer, 1980LLK
~8.8EIVan Veen, 1976LLK
8.80 ± 0.05EIThorstad and Undheim, 1974LLK
8.90PEClark, Gleiter, et al., 1973LLK
9.05CTSAloisi and Pignataro, 1973LLK
8.874 ± 0.005SDiLonardo, Galloni, et al., 1972LLK
9.12 ± 0.05EILinda, Marino, et al., 1971LLK
8.87 ± 0.01PEDerrick, Asbrink, et al., 1971LLK
8.86 ± 0.01PIPotapov and Bazhenov, 1970RDSH
8.80 ± 0.05PEBaker, Betteridge, et al., 1970RDSH
8.87 ± 0.05PEEland, 1969RDSH
8.860 ± 0.005PIWatanabe, Nakayama, et al., 1962RDSH
8.95 ± 0.02SPrice and Walsh, 1941RDSH
8.85PEBajic, Humski, et al., 1985Vertical value; LBLHLM
8.90PEBock and Roth, 1983Vertical value; LBLHLM
8.90PEMellink and Janssen, 1978Vertical value; LLK
8.85PEBozic, Humski, et al., 1977Vertical value; LLK
8.87PESchafer, Schweig, et al., 1973Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
CHS+13.0 ± 0.2C3H3CEMSTedder and Vidaud, 1980LLK
CHS+13.19 ± 0.04C3H3PEButler and Baer, 1980LLK
CHS+13.0 ± 0.2?EIKhvostenko, 1962RDSH
C2H2S+12.5 ± 0.2C2H2CEMSTedder and Vidaud, 1980LLK
C2H2S+12.1 ± 0.1C2H2PEButler and Baer, 1980LLK
C2H2S+10.8 ± 0.2?EIKhvostenko, 1962RDSH
C3HS+12.95 ± 0.05CH3PEButler and Baer, 1980LLK
C3H3+13.0 ± 0.2CHSCEMSTedder and Vidaud, 1980LLK
C3H3+13.06 ± 0.05CHSPEButler and Baer, 1980LLK
C3H3+12.8 ± 0.2?EIKhvostenko, 1962RDSH
C4H3S+12.93 ± 0.07HPEButler and Baer, 1980LLK
S+20.0 ± 0.5?EIStepanov, Perov, et al., 1988LL

De-protonation reactions

C4H3S- + Hydrogen cation = Thiophene

By formula: C4H3S- + H+ = C4H4S

Quantity Value Units Method Reference Comment
Δr381.2 ± 3.1kcal/molG+TSDePuy, Kass, et al., 1988gas phase; Between MeOH, EtOH. D exchange implies anion at C-2.; B
Quantity Value Units Method Reference Comment
Δr373.0 ± 3.0kcal/molIMRBDePuy, Kass, et al., 1988gas phase; Between MeOH, EtOH. D exchange implies anion at C-2.; B

References

Go To: Top, Reaction thermochemistry 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.

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

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