IMes

IMes
Names
Preferred IUPAC name
1,3-Bis(2,4,6-trimethylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene
Other names
1,3-Dimesitylimidazol-2-ylidene, 1,3-bis(2,4,6-trimethylphenyl)-imidazolium, 1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.154.201 Edit this at Wikidata
  • InChI=1S/C21H24N2/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/h7-12H,1-6H3
    Key: JCYWCSGERIELPG-UHFFFAOYSA-N
  • InChI=1/C21H24N2/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/h7-12H,1-6H3
    Key: JCYWCSGERIELPG-UHFFFAOYAJ
  • Cc1cc(c(c(c1)C)N2C=CN([C]2)c3c(cc(cc3C)C)C)C
Properties
C21H24N2
Molar mass 304.43
Appearance white solid
Melting point 150 to 155 °C (302 to 311 °F; 423 to 428 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

IMes is an abbreviation for an organic compound that is a common ligand in organometallic chemistry. It is an N-heterocyclic carbene (NHC). The compound, a white solid, is often not isolated but instead is generated upon attachment to the metal centre.[1]

First prepared by Arduengo,[2] the heterocycle is synthesized by condensation of 2,4,6-trimethylaniline and glyoxal to give the diimine. In the presence of acid, the resulting glyoxal-bis(mesitylimine) condenses with formaldehyde to give the dimesitylimidazolium cation. This cation is the conjugate acid of the NHC.[3][4]

  1. ^ Cite error: The named reference Nolan was invoked but never defined (see the help page).
  2. ^ Arduengo, Anthony J.; Dias, H. V. Rasika; Harlow, Richard L.; Kline, Michael (1992). "Electronic stabilization of nucleophilic carbenes". Journal of the American Chemical Society. 114 (14): 5530–5534. doi:10.1021/ja00040a007.
  3. ^ Ison, Elon A.; Ison, Ana (2012). "Synthesis of Well-Defined Copper N-Heterocyclic Carbene Complexes and Their Use as Catalysts for a "Click Reaction": A Multistep Experiment That Emphasizes the Role of Catalysis in Green Chemistry". Journal of Chemical Education. 89 (12): 1575–1577. Bibcode:2012JChEd..89.1575I. doi:10.1021/ed300243s.
  4. ^ Chen, Junting; Ritter, Tobias (2019). "Late-Stage Deoxyfluorination of Phenols with PhenoFluorMix". Org. Synth. 96: 16. doi:10.15227/orgsyn.096.0016.