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Experimental and computational studies on the formation of three para-benzyne analogues in the gas phase
Experimental and computational studies on the formation of three gaseous, positively-charged para-benzyne analogues in a Fourier transform ion cyclotron resonance (FT-ICR) mass spectrometer are reported. The structures of the cations were examined by isolating them and allowing them to react with various neutral reagents whose reactions with aromatic carbon-centered sigma-type mono- and biradicals are well understood. Cleavage of two iodine-carbon bonds in N-deuterated 1,4-diiodoisoquinolinium cation by collision-activated dissociation (CAD) produced a long-lived cation that showed nonradical reactivity, which was unexpected for a para-benzyne. However, the reactivity closely resembles that of an isomeric enediyne, N-deuterated 2-ethynylbenzonitrilium cation. A theoretical study on possible rearrangement reactions occurring during CAD revealed that the cation formed upon the first iodine atom loss undergoes ring-opening before the second iodine atom loss to form an enediyne instead of a para-benzyne. Similar results were obtained for the 5,8-didehydroisoquinolinium cation and the 2,5-didehydropyridinium cation. The findings for the 5,8-didehydroisoquinolinium cation are in contradiction with an earlier report on this cation. The cation described in the literature was regenerated by using the literature method and demonstrated to be the isomeric 5,7-didehydro- isoquinolinium cation and not the expected 5,8-isomer. Pick the right isomer! The generation of three positively charged para-benzyne analogues was attempted in an FT-ICR mass spectrometer. The experimental and quantum chemical findings indicate that the monoradical precursors for the para-benzynes undergo ring-opening faster than formation of the para-benzyne by iodine atom elimination, thus generating enediyne isomers of the para-benzynes (see scheme). Copyright
Note that a catalyst decreases the activation energy for both the forward and the reverse reactions and hence accelerates both the forward and the reverse reactions.Safety of Isoquinolin-8-amine, you can also check out more blogs about23687-27-6
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Isoquinoline – Wikipedia,
Isoquinoline | C9H284N – PubChem