Chemistry:Tetramethylthiourea
From HandWiki
Tetramethylthiourea is an organosulfur compound with the formula ((CH
3)
2N)
2C=S. This commercially available compound is used as a ligand in homogeneous catalysis and in organic synthesis.
Structure
The core of the compound is thiourea, with each nitrogen connected to two methyl groups. The molecule is planar. The C=S bond is 0.02 Å shorter than in thiourea itself.[1]
Reactions
Sulfur is the basic site in tetramethylthiourea. Alkylation occurs at S, affording isothiouronium salts.[2]
Tetramethylthiourea forms many coordination complexes. Two examples tetrahedral CoCl
2L
2 and linear AuBrL, where L = ((CH
3)
2N)
2C=S.[3][4]
References
- ↑ Jones, Peter G.; Taouss, Christina; Teschmit, Nicole; Thomas, Lena (2013). "Methylthioureas and Their Morpholine and Dioxane Adducts; Hydrogen-Bonding Patterns". Acta Crystallographica Section B Structural Science, Crystal Engineering and Materials 69 (4): 405–413. doi:10.1107/S2052519213013481. PMID 23873066.
- ↑ Clovis Peppe; Rafael Pavão das Chagas; Claudio Martins Pereira de Pereira (15 March 2007). "Tetramethylthiourea". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/9780470842898.rn00711. ISBN 978-0-471-93623-7.
- ↑ Vaidya, Shefali; Shukla, Pragya; Tripathi, Shalini; Rivière, Eric; Mallah, Talal; Rajaraman, Gopalan; Shanmugam, Maheswaran (2018). "Substituted versus Naked Thiourea Ligand Containing Pseudotetrahedral Cobalt(II) Complexes: A Comparative Study on Its Magnetization Relaxation Dynamics Phenomenon". Inorganic Chemistry 57 (6): 3371–3386. doi:10.1021/acs.inorgchem.8b00160. PMID 29485862.
- ↑ Fabretti, Antonio C.; Giusti, Aleardo; Malavasi, Wanda (1990). "Reaction Products Between Gold(III) Bromide and Tetramethylthiourea: Dibromobis(tetramethylthiourea)gold(III) Dibromoaurate(I) and Bromo(tetramethylthiourea)gold(I). Synthesis, Crystal and Molecular Structure, and Infrared Spectra". Journal of the Chemical Society, Dalton Transactions (10): 3091. doi:10.1039/dt9900003091.
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