SIMes

Last updated
SIMes
SIMes.png
Names
IUPAC name
1,3-Bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene
Other names
IMesH2, H2IMes, 1,3-Dimesityl-imidazol-4,5-dihydro-2-ylidene
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/C21H26N2/c1-14-9-16(3)20(17(4)10-14)22-7-8-23(13-22)21-18(5)11-15(2)12-19(21)6/h9-12H,7-8H2,1-6H3
    Key: LSMWOQFDLBIYPM-UHFFFAOYSA-N
  • Cc1cc(C)c(c(C)c1)N2CCN([C]2)c3c(C)cc(C)cc3C
Properties
C21H26N2
Molar mass 306.453 g·mol−1
Melting point 79 to 85 °C (174 to 185 °F; 352 to 358 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

SIMes (or H2Imes) is an N-heterocyclic carbene. It is a white solid that dissolves in organic solvents. The compound is used as a ligand in organometallic chemistry. It is structurally related to the more common ligand IMes but with a saturated backbone (the S of SIMes indicates a saturated backbone). It is slightly more flexible and is a component in Grubbs II. [1] It is prepared by alkylation of trimethylaniline by dibromoethane followed by ring closure and dehydrohalogenation. [2]

References

  1. ↑ Nolan, Steven P. (2006). N-Heterocyclic Carbenes in Synthesis. Wiley-VCH. ISBN   978-3-527-60940-6.
  2. ↑ "Synthesis of 1,3–bis(2,4,6–trimethylphenyl)–imidazolinium salts : SIMes.HCl, SIMes.HBr, SIMes.HBF4 and SIMes.HPF6. : Protocol Exchange". www.nature.com. 10 October 2012. Retrieved 2017-09-25.
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