New Advances in Chemical Research, April 2021.The transformation of simple hydrocarbons into more complex and valuable products via catalytic C–H bond functionalisation has revolutionised modern synthetic chemistry. 5959-52-4, Name is 3-Amino-2-naphthoic acid, SMILES is NC1=CC2=C(C=CC=C2)C=C1C(O)=O, belongs to naphthyridine compound. In a document, author is Jin, Qiuyan, introduce the new discover, SDS of cas: 5959-52-4.
A combination of gas-phase ion trap mass spectrometry experiments and density functional theory (DFT) calculations have been used to examine the role of substituents on the decarboxylation of 25 different coordinated aromatic carboxylates in binuclear complexes, [(napy)Cu-2(O2CC6H4X)](+), where napy is the ligand 1,8-naphthyridine (molecular formula, C8H6N2) and X=H and the ortho (o), meta (m) and para (p) isomers of F, Br, CN, NO2, CF3, OAc, Me and MeO. Two competing unimolecular reaction pathways were found: decarboxylation to give the organometallic cation [(napy)Cu-2(C6H4X)](+) or loss of the neutral copper benzoate to yield [(napy) Cu](+). The substituents on the aryl group influence the branching ratios of these product channels, but decarboxylation is always the dominant pathway. Density functional theory calculations reveal that decarboxylation proceeds via two transition states. The first enables a change in the coordination mode of the coordinated benzoate in [(napy)Cu-2(O2CC6H4X)](+) from the thermodynamically favoured O, O-bridged form to the O-bound form, which is the reactive conformation for the second transition state which involves extrusion of CO2 with concomitant formation of the CO2 coordinated organometallic cation, [(napy)Cu-2(C6H4X)(CO2)](+), which then loses CO2 in the final step to yield [(napy)Cu-2(C6H4X)](+). In all cases the barrier is highest for the second transition state. The o-substituted benzoates show a lower activation energy than the m-substituted ones, while the p-substituted ones have the highest energy, which is consistent with the experimentally determined normalised collision energy required to induce fragmentation of [(napy)Cu-2(O2CC6H4X)](+).
Therefore, this conceptually novel strategy might open impressive avenues to establish green and sustainable chemistry platforms. If you like, you can also browse other articles about this kind. Thanks for taking the time to read the blog about 5959-52-4, SDS of cas: 5959-52-4.
Reference:
1,8-Naphthyridine – Wikipedia,
,1,8-Naphthyridine | C8H6N2 – PubChem