Trithiocarbonic acid

Structural formula
General
Surname	Trithiocarbonic acid
other names	Carbonotrithioic acid; Thiocarbonic acid;
Molecular formula	H 2 CS 3
Brief description	red, oily, pungent smelling liquid
External identifiers / databases
EC number	209-822-6
ECHA InfoCard	100.008.931
PubChem	68982
Wikidata	Q6582745
properties
Molar mass	110.21 g mol −1
density	1.47 g cm −3
Melting point	-26.9 ° C
boiling point	57 ° C (decomposition)
solubility	soluble in diethyl ether , chloroform and toluene
Refractive index	1.8225 (20 ° C)
safety instructions
GHS hazard labeling ; no classification available
GHS hazard labeling ; no classification available
Thermodynamic properties
ΔH f 0	24.0 kJ / mol
	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

The trithiocarbonic acid is one of carbonic acid analog acid, in which the three oxygen atoms are substituted by sulfur. In contrast to thio and dithiocarbonic acid, it is relatively stable. In 1928 Mills and Robinson succeeded for the first time in the synthesis of the pure substance from ammonium trithiocarbonate and hydrogen sulfide .

Extraction and presentation

Trithiocarbonic acid can be obtained by reacting barium trithiocarbonate with hydrogen chloride in water.

Derivatives

The anhydride of trithiocarbonic acid is carbon disulfide .

literature

Franz Runge, Zaki El-Hewehi: On the knowledge of trithiocarbonic acid. I. About aliphatic and araliphatic trithiocarbonic acid diesters. In: Journal for practical chemistry . 7, 1959, pp. 268-278, doi : 10.1002 / prac.19590070504 ( PDF ).

Franz Runge, Zaki El-Hewehi, Eberhard Taeger: On the knowledge of trithiocarbonic acid. II. Preparation of trithiocarbonic acid diester through the reaction of thiophosgene with thiols and thiophenols. In: J. Prakt. Chem. 7, 1959, pp. 279-285, doi : 10.1002 / prac.19590070505 ( PDF ).

Zaki El-Hewehi, Franz Runge: On the knowledge of trithiocarbonic acid. III. About the usability of trithiocarbonic acid diesters as "additives" and pickling agents. In: J. Prakt. Chem. 9, 1959, pp. 33-42, doi : 10.1002 / prac.19590090108 ( PDF ).

Franz Runge, Zaki El-Hewehi, Hans-Joachim Renner, Eberhard Taeger: On the knowledge of trithiocarbonic acid. IV. About the production and properties of trithiocarbonic acid diesters and their usability as pesticides. In: J. Prakt. Chem. 11, 1960, pp. 284-308, doi : 10.1002 / prac.19600110507 ( PDF ).

Franz Runge, Zaki El-Hewehi, Eberhard Taeger: On the knowledge of trithiocarbonic acid. V. On the synthesis and biological properties of heterocyclic trithiocarbonic acid diesters. In: J. Prakt. Chem. 18, 1962, pp. 262-268, doi : 10.1002 / prac.19620180504 . ( PDF )

Eberhard Taeger, Zaki El-Hewehi, Franz Runge: On the knowledge of trithiocarbonic acid. VI. About the reaction of aromatic and heterocyclic trithiocarbonic acid diesters with diazomethane and phenyldiazomethane. In: J. Prakt. Chem. 18, 1962, pp. 269-274, doi : 10.1002 / prac.19620180505 ( PDF ).

Zaki El-Hewehi, Eberhard Taeger, Franz Runge: On the knowledge of trithiocarbonic acid. VII. About the reaction of aromatic and heterocyclic trithiocarbonic acid diesters with primary and secondary amines, hydrazine and phenylhydrazine. In: J. Prakt. Chem. 18, 1962, pp. 275–282, doi : 10.1002 / prac.19620180506 ( PDF )

Zaki El-Hewehi, Eberhard Taeger, Franz Runge: On the knowledge of trithiocarbonic acid. VIII. On the effect of halogen on trithiocarbonic acid diesters. In: J. Prakt. Chem. 18, 1962, pp. 283-286, doi : 10.1002 / prac.19620180507 ( PDF ).

Individual evidence

↑ ^a ^b ^c ^d Entry on trithiocarbonic acid. In: Römpp Online . Georg Thieme Verlag, accessed on January 17, 2014.
^ ^A ^b A. F. Holleman , E. Wiberg , N. Wiberg : Textbook of Inorganic Chemistry . 101st edition. Walter de Gruyter, Berlin 1995, ISBN 3-11-012641-9 , p. 872.
↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-514.
↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
↑ 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. 5-20.
↑ Trithiocarbonates: Synthesis and structure elucidation of inorganic salts of the anion of trithiocarbonic acid.
↑ H. Mills, PC Robinson, J. Chem. Soc. 1928, 1, 2326-2332.
↑ Peter Paetzold: Chemistry an introduction . Walter de Gruyter, 2009, ISBN 978-3-11-020268-7 , pp. 501 ( limited preview in Google Book search).

[Römpp-1] Entry on trithiocarbonic acid. In: Römpp Online . Georg Thieme Verlag, accessed on January 17, 2014.

[Holleman-Wiberg_101-2] A ^b A. F. Holleman , E. Wiberg , N. Wiberg : Textbook of Inorganic Chemistry . 101st edition. Walter de Gruyter, Berlin 1995, ISBN 3-11-012641-9 , p. 872.

[CRC90_3_514-3] David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-514.

[NV-4] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[CRC90_5_20-5] 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. 5-20.

[6] Trithiocarbonates: Synthesis and structure elucidation of inorganic salts of the anion of trithiocarbonic acid.

[7] H. Mills, PC Robinson, J. Chem. Soc. 1928, 1, 2326-2332.

[Peter_Paetzold-8] Peter Paetzold: Chemistry an introduction . Walter de Gruyter, 2009, ISBN 978-3-11-020268-7 , pp. 501 ( limited preview in Google Book search).