Thiophene, 2,3-dihydro-
- Formula: C4H6S
- Molecular weight: 86.155
- IUPAC Standard InChI: InChI=1S/C4H6S/c1-2-4-5-3-1/h1,3H,2,4H2
- IUPAC Standard InChIKey: OXBLVCZKDOZZOJ-UHFFFAOYSA-N
- CAS Registry Number: 1120-59-8
- 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: 2,3-Dihydrothiophene; Dihydro-2-(3H)-thiophene
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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
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | 90.7 ± 1.3 | kJ/mol | Ccr | Davies and Sunner, 1962 | Reanalyzed by Cox and Pilcher, 1970, Original value = 91.1 ± 1.3 kJ/mol |
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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°liquid | 52.9 ± 1.2 | kJ/mol | Ccr | Davies and Sunner, 1962 | Reanalyzed by Cox and Pilcher, 1970, Original value = 53.4 ± 1.2 kJ/mol |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -3086.8 ± 1.0 | kJ/mol | Ccr | Davies and Sunner, 1962 | Reanalyzed by Cox and Pilcher, 1970, Original value = -3087.2 ± 1.0 kJ/mol |
Phase change 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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| Tboil | 385.2 | K | N/A | Majer and Svoboda, 1985 | |
| Tboil | 385.15 | K | N/A | Davies and Sunner, 1962, 2 | Uncertainty assigned by TRC = 0.6 K; TRC |
| Quantity | Value | Units | Method | Reference | Comment |
| Tfus | 164.45 | K | N/A | Davies and Sunner, 1962, 2 | Uncertainty assigned by TRC = 1.5 K; TRC |
| Tfus | 163.55 | K | N/A | Davies and Sunner, 1962, 2 | Uncertainty assigned by TRC = 1. K; TRC |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔvapH° | 37.79 | kJ/mol | N/A | Majer and Svoboda, 1985 | |
| ΔvapH° | 37.7 ± 0.4 | kJ/mol | C | Davies and Sunner, 1962 | ALS |
| ΔvapH° | 37.8 | kJ/mol | N/A | Davies and Sunner, 1962 | DRB |
Enthalpy of vaporization
| ΔvapH (kJ/mol) | Temperature (K) | Reference |
|---|---|---|
| 33.24 | 385.2 | Majer and Svoboda, 1985 |
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 compiled by: Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
View reactions leading to C4H6S+ (ion structure unspecified)
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 8.11 | PE | Kuhn, Klessinger, et al., 1987 | Vertical value |
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
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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 | Chemical Concepts |
| NIST MS number | 151458 |
Gas Chromatography
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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
Van Den Dool and Kratz RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | CP Sil 8 CB | 767. | Elmore, Campo, et al., 2002 | 60. m/0.25 mm/0.25 μm, He, 40. C @ 2. min, 4. K/min; Tend: 280. C |
| Capillary | BPX-5 | 768. | Ames, Guy, et al., 2001 | 50. m/0.32 mm/0.5 μm, He, 60. C @ 5. min, 4. K/min, 250. C @ 10. min |
Van Den Dool and Kratz RI, non-polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | CP-Sil 8CB-MS | 764. | Elmore, Mottram, et al., 2000 | 60. m/0.25 mm/0.25 μm, He; Program: 0C(5min) => 40C/min => 40C (2min) => 4C/min => 280C |
| Capillary | BPX-5 | 780. | Elmore, Mottram, et al., 1999 | 50. m/0.32 mm/0.5 μm, He; Program: 0C(5min) => 40C/min => 40C(2min) => 4C/min => 280C |
Normal alkane RI, polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | DB-Wax | 1104. | Umano, Hagi, et al., 1995 | He, 40. C @ 2. min, 2. K/min; Column length: 60. m; Column diameter: 0.25 mm; Tend: 200. C |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Davies and Sunner, 1962
Davies, J.V.; Sunner, S.,
Heats of combustion and formation of thiolane and of the thiolenes,
Acta Chem. Scand., 1962, 16, 1870-1876. [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]
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]
Davies and Sunner, 1962, 2
Davies, J.V.; Sunner, S.,
Heats of Combustion and Formation of Thiolane and the Thiolenes,
Acta Chem. Scand., 1962, 16, 1870. [all data]
Kuhn, Klessinger, et al., 1987
Kuhn, H.J.; Klessinger, M.; Ruscic, B.; Klasinc, L.,
On the empirical correlation schemes for ionization energies in ring compounds,
Int. J. Mass Spectrom. Ion Phys., 1987, 43, 147. [all data]
Elmore, Campo, et al., 2002
Elmore, J.S.; Campo, M.M.; Enser, M.; Mottram, D.S.,
Effect of lipid composition on meat-like model systems containing cysteine, ribose, and polyunsaturated fatty acids,
J. Agric. Food Chem., 2002, 50, 5, 1126-1132, https://doi.org/10.1021/jf0108718
. [all data]
Ames, Guy, et al., 2001
Ames, J.M.; Guy, R.C.E.; Kipping, G.J.,
Effect of pH and temperature on the formation of volatile compounds in cysteine/reducing sugar/starch mixtures during extrusion cooking,
J. Agric. Food Chem., 2001, 49, 4, 1885-1894, https://doi.org/10.1021/jf0012547
. [all data]
Elmore, Mottram, et al., 2000
Elmore, J.S.; Mottram, D.S.; Enser, M.; Wood, J.D.,
The effects of diet and breed on the volatile compounds of cooked lamb,
Meat Sci., 2000, 55, 2, 149-159, https://doi.org/10.1016/S0309-1740(99)00137-0
. [all data]
Elmore, Mottram, et al., 1999
Elmore, J.S.; Mottram, D.S.; Enser, M.; Wood, J.D.,
Effect of the polyunsaturated fatty acid composition of beef muscle on the profile of aroma volatiles,
J. Agric. Food Chem., 1999, 47, 4, 1619-1625, https://doi.org/10.1021/jf980718m
. [all data]
Umano, Hagi, et al., 1995
Umano, K.; Hagi, Y.; Nakahara, K.; Shyoji, A.; Shibamoto, T.,
Volatile chemicals formed in the headspace of a heated D-glucose/L-cysteine Maillard model system,
J. Agric. Food Chem., 1995, 43, 8, 2212-2218, https://doi.org/10.1021/jf00056a046
. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, References
- Symbols used in this document:
Tboil Boiling point Tfus Fusion (melting) point ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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