Thiophene, 2-methyl-

• Formula: C₅H₆S
• Molecular weight: 98.166
• IUPAC Standard InChI: InChI=1S/C5H6S/c1-5-3-2-4-6-5/h2-4H,1H3 Copy

  
• IUPAC Standard InChIKey: XQQBUAPQHNYYRS-UHFFFAOYSA-N Copy
• 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
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• Other names: 2-Methylthiophene; 2-Methylthiacyclopentadiene; 2-methylthiacyclopentadiene (2-methylthiophene)
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• Information on this page:
  • Gas phase thermochemistry data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
  • Phase change data
  • Henry's Law data
  • Gas Chromatography
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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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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 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

Gas phase ion energetics 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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

Ionization energy determinations

De-protonation reactions

C₅H₅S^- +  =

By formula: C₅H₅S^- + H⁺ = C₅H₆S

Mass spectrum (electron ionization)

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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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Additional Data

UV/Visible spectrum

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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: Victor Talrose, Alexander N. Yermakov, Alexy A. Usov, Antonina A. Goncharova, Axlexander N. Leskin, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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Additional Data

References

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible spectrum, 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]

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]

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]

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]

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]

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]

Colonna, Distefano, et al., 1979
Colonna, F.P.; Distefano, G.; Guerra, M.; Jones, D.; Modelli, A., Furyl- and thienyl-mercury derivatives studied by means of ultraviolet photoelectron spectroscopy. Evidence for the participation in bonding of the vacant 6p π orbitals of mercury in bis-2-furyl-bis-2-thienylmercury, J. Chem. Soc. Dalton Trans., 1979, 2037. [all data]

Capaigne and Diedrich, 1951
Capaigne, E.; Diedrich, J.L., J. Am. Chem. Soc., 1951, 73, 5240. [all data]

Notes

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible spectrum, References

• Symbols used in this document:
  

  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

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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