Thiophene, 2-chloro-
- Formula: C4H3ClS
- Molecular weight: 118.585
- IUPAC Standard InChIKey: GSFNQBFZFXUTBN-UHFFFAOYSA-N
- CAS Registry Number: 96-43-5
- 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: 2-Chlorothiophene; 2-Thienyl chloride
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Phase change 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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 401.5 | K | N/A | Weast and Grasselli, 1989 | BS |
Tboil | 401.65 | K | N/A | Khodeir, Skulski, et al., 1986 | Uncertainty assigned by TRC = 1.5 K; TRC |
Tboil | 465.65 | K | N/A | Khodeir, Skulski, et al., 1986 | Uncertainty assigned by TRC = 1.5 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 201. | K | N/A | Fujimori and Oguni, 1993 | Uncertainty assigned by TRC = 0.1 K; TRC |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
8.29 | 328. | N/A | Dykyj, Svoboda, et al., 1999 | Based on data from 313. to 401. K.; AC |
8.82 | 335. | N/A | Dykyj, Svoboda, et al., 1999 | Based on data from 320. to 401. K. See also Ditsent, Skorokhodov, et al., 1981.; AC |
8.22 | 348. | A,I | Stephenson and Malanowski, 1987 | Based on data from 333. to 374. K. See also Eon, Pommier, et al., 1971 and Dykyj, Svoboda, et al., 1999.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (atm)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
333.4 to 373.5 | 4.52225 | 1792.85 | -0.598 | Eon, Pommier, et al., 1971 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
2.143 | 201.30 | Fujimori and Oguni, 1993, 2 | DH |
2.14 | 201.3 | Fujimori and Oguni, 1993, 3 | AC |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
10.65 | 201.30 | Fujimori and Oguni, 1993, 2 | DH |
Gas phase ion energetics data
Go To: Top, Phase change 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:
L - Sharon G. Lias
Data compiled as indicated in comments:
LL - Sharon G. Lias and Joel F. Liebman
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 |
---|---|---|---|---|---|
IE (evaluated) | 8.74 ± 0.04 | eV | N/A | N/A | L |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.78 | PE | Veszpremi, Nyulaszi, et al., 1988 | LL |
8.83 | CTS | Aloisi and Pignataro, 1973 | LLK |
9.06 ± 0.05 | EI | Linda, Marino, et al., 1971 | LLK |
8.70 ± 0.05 | PE | Baker, Betteridge, et al., 1970 | RDSH |
8.68 ± 0.01 | PI | Watanabe, 1957 | RDSH |
8.89 ± 0.05 | PE | Fringuelli, Marino, et al., 1976 | Vertical value; LLK |
References
Go To: Top, Phase change 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.
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]
Khodeir, Skulski, et al., 1986
Khodeir, N.M.; Skulski, L.; Wroczynski, P.,
Preparation of 2-Chlorofuran and 2-Chlorothiophene from the Respective Furan and Thiophene Mercurials and Disulfur Dichloride,
Bull. Pol. Acad. Sci., Chem., 1986, 34, 443. [all data]
Fujimori and Oguni, 1993
Fujimori, H.; Oguni, M.,
Construction of an adiabatic calorimeter at low-temp and glass transition of crystalline 2-bromothiophene,
J. Phys. Chem. Solids, 1993, 54, 271. [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]
Ditsent, Skorokhodov, et al., 1981
Ditsent, V.E.; Skorokhodov, I.I.; Zolotareva, M.N.; Savuskina, V.I.; Tabenko, B.N.,
Zh. Prikl. Khim. (Leningrad), 1981, 54, 1617. [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]
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]
Fujimori and Oguni, 1993, 2
Fujimori, H.; Oguni, M.,
Thermodynamic study of 2-chlorothiophene: observation of two subsequent glass transitions in the stable crystalline state,
J. Phys. Chem. Solids, 1993, 54(5), 607-612. [all data]
Fujimori and Oguni, 1993, 3
Fujimori, H.; Oguni, M.,
Construction of an adiabatic calorimeter at low temperatures and glass transition of crystalline 2-bromothiophene,
J. Phys. Chem. Solids, 1993, 54(2), 271-280. [all data]
Veszpremi, Nyulaszi, et al., 1988
Veszpremi, T.; Nyulaszi, L.; Zsombok, G.Y.,
Systematic hel UPS study of chlorothiophenes,
J. Electron Spectrosc. Relat. Phenom., 1988, 46, 269. [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]
Watanabe, 1957
Watanabe, K.,
Ionization potentials of some molecules,
J. Chem. Phys., 1957, 26, 542. [all data]
Fringuelli, Marino, et al., 1976
Fringuelli, F.; Marino, G.; Taticchi, A.; Distefano, G.; Colonna, F.P.; Pignataro, S.,
Photoelectron spectra of the α-substituted derivatives of furan, thiophen, selenophen, and tellurophen. A comparative study of the molecular orbital energies,
J. Chem. Soc. Perkin Trans. 2, 1976, 276. [all data]
Notes
Go To: Top, Phase change data, Gas phase ion energetics data, References
- Symbols used in this document:
IE (evaluated) Recommended ionization energy Tboil Boiling point Ttriple Triple point temperature ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔvapH Enthalpy of vaporization - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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