Inhibition of the Cyclotrimerization of Benzonitrile and the Likely Mechanism of the Cyclotrimerization Process:  Structure of a New Tetrameric α-Amino Lithium Imide Demonstrating <i>Intra</i>molecular Stabilization of the Metal Centers Robert P. Davies Paul R. Raithby Gregory P. Shields Ronald Snaith Andrew E. H. Wheatley 10.1021/om961082w.s002 https://acs.figshare.com/articles/dataset/Inhibition_of_the_Cyclotrimerization_of_Benzonitrile_and_the_Likely_Mechanism_of_the_Cyclotrimerization_Process_Structure_of_a_New_Tetrameric_-Amino_Lithium_Imide_Demonstrating_i_Intra_i_molecular_Stabilization_of_the_Metal_Centers/3779322 Reaction of ((2-(dimethylamino)ethyl)methylamino)lithium (<b>4</b>) with benzonitrile gives a new α-amino lithium imide, <b>5</b>, which in the solid state is a tetrameric cubane. Aggregation is accompanied by chelation of each metal center using a tertiary amino function, yielding stable seven-membered rings. The stability of <b>5</b> limits cyclotrimerization of the benzonitrile moiety to 2,4,6-triphenyl-1,3,5-triazine, thereby suggesting a likely mechanism for the cyclotrimerization process. 1997-05-13 00:00:00 stability tetrameric cubane lithium imide dimethylamino New Lithium Benzonitrile Aggregation mechanism Imide Inhibition Cyclotrimerization Tetrameric Likely Mechanism 5 limits cyclotrimerization function triphenyl cyclotrimerization process Stabilization metal center chelation Metal Centers Reaction benzonitrile moiety Intra Amino