Thiiran
Structural formula | ||||||||||||||||
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General | ||||||||||||||||
Surname | Thiiran | |||||||||||||||
other names |
Ethylene sulfide |
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Molecular formula | C 2 H 4 S | |||||||||||||||
Brief description |
clear colorless liquid with an unpleasant odor |
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External identifiers / databases | ||||||||||||||||
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properties | ||||||||||||||||
Molar mass | 60.12 g mol −1 | |||||||||||||||
Physical state |
liquid |
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density |
1.01 g cm −3 |
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boiling point |
55-56 ° C |
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Vapor pressure |
287 h Pa (20 ° C) |
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Refractive index |
1.495 (20 ° C) |
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safety instructions | ||||||||||||||||
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Toxicological data | ||||||||||||||||
Thermodynamic properties | ||||||||||||||||
ΔH f 0 |
51.6 kJ / mol |
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As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C |
Thiirane , also called ethylene sulfide , is a sulfur-containing saturated three-membered heterocycle and thus the simplest representative of the thiirane group .
presentation
Thiirane is prepared by reacting ethylene oxide with thiourea in an aqueous medium with cooling. This creates thiirane and urea .
Another possibility is the reaction of ethylene carbonate with potassium thiocyanate , which produces carbon dioxide and potassium cyanate in addition to thiirane .
properties
Ethylene sulfide is a liquid at room temperature compound having a boiling point at 55-56 ° C. The bond length between carbon and sulfur is 181.9 pm , between two carbons 149.2 pm. The bond angle at the sulfur atom is 65 ° 48 '.
Reactions
Thiirane reacts with nucleophiles with ring opening. It can therefore be used for the synthesis of terminal thiols . Amines or thiols, for example, can act as nucleophiles .
It reacts with imines to form thiazolidines.
However, the sulfur atom of thiirane can also serve as a nucleophile itself.
Individual evidence
- ↑ a b c d e f g h data sheet Ethylene sulfide from Sigma-Aldrich , accessed on April 24, 2011 ( PDF ).
- ↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Standard Thermodynamic Properties of Chemical Substances, pp. 5-22.
- ↑ JF Olin, FB Dains in: J. Am. Chem. Soc. 1930, 52, 3322-3327. doi : 10.1021 / ja01371a047
- ↑ GL Cunningham, AW Boyd, RJ Myers, WD Gwinn in: J. Chem. Phys. 1951, 19, 6, 676-685; doi : 10.1063 / 1.1748331 .
- ^ MD Rozwadowska, A. Sulima in: Tetrahedron 2001 , 57 , 3499-3506. doi : 10.1016 / S0040-4020 (01) 00224-1