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Thiophene, 2-methyl-

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Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Deltafgas84.35 ± 0.92kJ/molCcrPennington, Finke, et al., 1956 

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
Deltafliquid44.60 ± 0.92kJ/molCcrPennington, Finke, et al., 1956Reanalyzed by Cox and Pilcher, 1970, Original value = 45.44 ± 0.88 kJ/mol; ALS
Quantity Value Units Method Reference Comment
Deltacliquid-3472.0 ± 0.75kJ/molCcrPennington, Finke, et al., 1956Reanalyzed by Cox and Pilcher, 1970, Original value = -3471.3 ± 0.75 kJ/mol; ALS
Quantity Value Units Method Reference Comment
liquid218.49J/mol*KN/APennington, Finke, et al., 1956DH

Constant pressure heat capacity of liquid

Cp,liquid (J/mol*K) Temperature (K) Reference Comment
149.83298.15Pennington, Finke, et al., 1956T = 12 to 340 K.; DH

Constant pressure heat capacity of solid

Cp,solid (J/mol*K) Temperature (K) Reference Comment
97.91199.70Carlson and Westrum, 1968glass phase; T = 110 to 200 K. Value is unsmoothed experimental datum.; DH

Phase change data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible 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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Kenneth Kroenlein director
AC - William E. Acree, Jr., James S. Chickos
DRB - Donald R. Burgess, Jr.
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
Tboil385.8KN/AWeast and Grasselli, 1989BS
Tboil385.7KN/AMajer and Svoboda, 1985 
Tboil385.15KN/ALevi and Nicholls, 1958Uncertainty assigned by TRC = 1.5 K; TRC
Tboil386.KN/AHaines, Helm, et al., 1956Uncertainty assigned by TRC = 0.3 K; TRC
Quantity Value Units Method Reference Comment
Tfus209.77KN/AHaines, Helm, et al., 1956Uncertainty assigned by TRC = 0.06 K; TRC
Quantity Value Units Method Reference Comment
Ttriple209.79KN/APennington, Finke, et al., 1956, 2Uncertainty assigned by TRC = 0.05 K; extrapolate 1/f to zero; TRC
Quantity Value Units Method Reference Comment
Tc606.2KN/AMajer and Svoboda, 1985 
Quantity Value Units Method Reference Comment
Deltavap38.91kJ/molN/AMajer and Svoboda, 1985 
Deltavap38.7kJ/molN/AReid, 1972AC
Deltavap39.8kJ/molN/APennington, Finke, et al., 1956DRB

Enthalpy of vaporization

DeltavapH (kJ/mol) Temperature (K) Method Reference Comment
33.9385.7N/AMajer and Svoboda, 1985 
37.2339.A,EBStephenson and Malanowski, 1987Based on data from 324. - 391. K. See also White, Barnard--Smith, et al., 1952 and Dykyj, Svoboda, et al., 1999.; AC
36.8348.IEon, Pommier, et al., 1971Based on data from 333. - 373. K. See also Boublik, Fried, et al., 1984.; AC
38.9343.VPennington, Finke, et al., 1956ALS

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) beta Tc (K) Reference Comment
344. - 386.54.250.2853606.2Majer 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 - 373.54.843441812.35-10.276Eon, Pommier, et al., 1971Coefficents calculated by NIST from author's data.

Enthalpy of fusion

DeltafusH (kJ/mol) Temperature (K) Reference Comment
11.142207.79Pennington, Finke, et al., 1956DH
9.47207.8Pennington, Finke, et al., 1956AC

Entropy of fusion

DeltafusS (J/mol*K) Temperature (K) Reference Comment
53.62207.79Pennington, Finke, et al., 1956DH

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 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- + Hydrogen cation = Thiophene, 2-methyl-

By formula: C5H5S- + H+ = C5H6S

Quantity Value Units Method Reference Comment
Deltar1589. ± 13.kJ/molG+TSDePuy, Kass, et al., 1988gas phase; Acid: 2-methylthiophene. Between MeOH, EtOH.
Quantity Value Units Method Reference Comment
Deltar1561. ± 13.kJ/molIMRBDePuy, Kass, et al., 1988gas phase; Acid: 2-methylthiophene. Between MeOH, EtOH.

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
0.424000.MN/A

Gas phase ion energetics data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Mass spectrum (electron ionization), UV/Visible 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

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

Quantity Value Units Method Reference Comment
Proton affinity (review)859.0kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity826.5kJ/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
8.61CTSAloisi and Pignataro, 1973LLK
8.63 ± 0.05EILinda, Marino, et al., 1971LLK
8.14PEBaker, Betteridge, et al., 1970RDSH
8.59PEColonna, Distefano, et al., 1979Vertical value; LLK

De-protonation reactions

C5H5S- + Hydrogen cation = Thiophene, 2-methyl-

By formula: C5H5S- + H+ = C5H6S

Quantity Value Units Method Reference Comment
Deltar1589. ± 13.kJ/molG+TSDePuy, Kass, et al., 1988gas phase; Acid: 2-methylthiophene. Between MeOH, EtOH.; B
Quantity Value Units Method Reference Comment
Deltar1561. ± 13.kJ/molIMRBDePuy, Kass, et al., 1988gas phase; Acid: 2-methylthiophene. Between MeOH, EtOH.; B

Mass spectrum (electron ionization)

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, UV/Visible 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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Mass spectrum
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Additional Data

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Owner NIST Mass Spectrometry Data Center
Collection (C) 2014 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin DC-24-1
NIST MS number 19749

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UV/Visible spectrum

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Mass spectrum (electron ionization), 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: 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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UVVis spectrum
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Additional Data

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Source Capaigne and Diedrich, 1951
Owner INEP CP RAS, NIST OSRD
Collection (C) 2007 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS
Source reference RAS UV No. 11097
Instrument Beckman DU
Melting point - 63.4
Boiling point 112.6

References

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

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]

Carlson and Westrum, 1968
Carlson, H.G.; Westrum, E.F., Jr., Thermal study of the glass-type transformation of 2-methylthiophene, J. Chem. Eng. Data, 1968, 13, 273-274. [all data]

Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [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]

Levi and Nicholls, 1958
Levi, L.; Nicholls, R.V.V., Formation of Styrene by Pyrolysis of Aromatic Heterocyclic Aldehyde- Aliphatic Acid Anhydride Mixtures on Morden Bentonite, Ind. Eng. Chem., 1958, 50, 1005. [all data]

Haines, Helm, et al., 1956
Haines, W.E.; Helm, R.V.; Cook, G.L.; Ball, J.S., Purification and Properties of Organic Sulfur Compounds, J. Phys. Chem., 1956, 60, 549-55. [all data]

Pennington, Finke, et al., 1956, 2
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, 2055-60. [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]

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]

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]

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]

Boublik, Fried, et al., 1984
Boublik, T.; Fried, V.; Hala, E., The Vapour Pressures of Pure Substances: Selected Values of the Temperature Dependence of the Vapour Pressures of Some Pure Substances in the Normal and Low Pressure Region, 2nd ed., Elsevier, New York, 1984, 972. [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 «sigma» and «pi» 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 «pi» 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, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible spectrum, References