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Abstract : The reaction of (NHC)ZnEt 2 (1)with 2,6-dimethylphenol in the molar ratio 1:2 at room temperature resulted in a monomeric zinc dimethylphenoxide [(NHC)Zn(OC 6 H 3 -2,6-Me 2 ) 2 ](NHC = 1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene)(2). Whereas, the reaction of 1 with 2,6-dimethylphenol in the presence of water in the molar ratios 1:2:0.5 or 1:2:1 afforded [(NHC) 2 Zn 2 (μ-OH)(μ-OC 6 H 3 -2,6-Me 2 )(OC 6 H 3 -2,6-Me 2 ) 2 ](3)and [(NHC)Zn(μ-OH)(OC 6 H 3 -2,6-Me 2 )] 2 (4)respectively. Moreover, reaction of 1 with 2,6-diisopropylphenol in the presence of a base led to the isolation of [(NHC)Zn(μ-OH)(OC 6 H 3 -2,6- i Pr 2 )] 2 (5). Compounds 2–5 have been fully characterized by spectroscopic and single crystal X-ray diffraction studies. In this paper, we have discussed the synthesis, structural characterizations of 2–5 and the mechanism for the formation of compounds 3–5 from 2. © 2019 Elsevier B.V.