Chemo-enzymatic cascade processes are invaluable due to their ability to rapidly construct high-value products from available feedstock chemicals in a one-pot relay manner. In an article, author is Podjed, Nina, once mentioned the application of 120-73-0, Name is Purine, molecular formula is C5H4N4, molecular weight is 120.11, MDL number is MFCD00079221, category is piperidines. Now introduce a scientific discovery about this category, Name: Purine.
From cyclic amines and acetonitrile to amidine zinc(ii) complexes
A seemingly simple combination of [Zn(quin)(2)(H2O)] (quin(-) = quinaldinate) and a selected secondary cyclic amine, piperidine (pipe), pyrrolidine (pyro) or morpholine (morph), afforded in acetonitrile a number of products: anionic homoleptic quinaldinate, neutral heteroleptic quinaldinate/amine and quinaldinate/amidine complexes. The piperidine and pyrrolidine systems underwent reaction with acetonitrile to give amidines. The in situ formed piperidinoacetamidine (pipeam) or pyrrolidinoacetamidine (pyroam) coordinated to zinc(ii). Reactions with piperidine led to trans-[Zn(quin)(2)(pipe)(2)]center dot 2CH(3)CN (1), [Zn(quin)(2)(pipe)]center dot cis-[Zn(quin)(2)(pipe)(2)] (2), pipeH[Zn(quin)(3)]center dot CH3CN (3), [Zn(quin)(2)(pipeam)]center dot CH3CN (4a), [Zn(quin)(2)(pipeam)]center dot 2CHCl(3) (4b), pipeamH[Zn(quin)(3)] (5) and pipeamH[Zn(quin)(2)(CH3COO)]center dot acetamide (6) (pipeH(+) and pipeamH(+) denote protonated amine or amidine). By analogy, [Zn(quin)(2)(pyro)(2)] (7), pyroH[Zn(quin)(3)]center dot CH3CN (8), pyroH[Zn(quin)(2)Cl] (9), [Zn(quin)(2)(pyroam)]center dot CH3CN center dot 0.5pyroam center dot 0.5H(2)O (10a), [Zn(quin)(2)(pyroam)]center dot 2CHCl(3) (10b), [Zn(quin)(2)(pyroam)]center dot CH2Cl2 (10c) and pyroamH[Zn(quin)(3)] (11) were obtained in the pyrrolidine reactions. The morpholine system allowed isolation of only two novel products, trans-[Zn(quin)(2)(morph)(2)] (12) and morphH[Zn(quin)(3)]center dot CH3CN (13). Importantly, no amidine could be isolated. Instead, in autoclaves at 105 degrees C morpholine degraded to ammonia, as confirmed by mass spectrometry of the gas phase. pyroamH[Zn(quin)(3)] exists in two polymorphs which differ in the binding modes of quinaldinate ligands. In 11triclinic, the metal ion of [Zn(quin)(3)](-) features a five-coordinate environment, whereas that in 11monoclinic is surrounded by six donors. Stabilities of the [Zn(quin)(3)](-) isomers were assessed with DFT calculations. The one with a six-coordinate zinc(ii) ion was found to be more stable than its five-coordinate counterpart. Favorable intermolecular interactions in the solid state stabilize both and reduce the energy difference between them. The calculations show the conversion of the five-coordinate [Zn(quin)(3)](-) into its coordinatively saturated isomer to be an almost barrierless process.
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Reference:
Piperidine – Wikipedia,
,Piperidine | C5H11N – PubChem