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NMR and DFT Study of the Copper(I)-Catalyzed Cycloaddition Reaction: H/D Scrambling of Alkynes and Variable Reaction Order of the Catalyst

Kalvet, I.; Tammiku-Taul, J.; Mäeorg, U.; Tämm, K.; Burk, P.; Sikk, L. (2016). NMR and DFT Study of the Copper(I)-Catalyzed Cycloaddition Reaction: H/D Scrambling of Alkynes and Variable Reaction Order of the Catalyst. ChemCatChem, 8 (10), 1804−1808. DOI: 10.1002/cctc.201600176.
artikkel ajakirjas
Kalvet, I.; Tammiku-Taul, J.; Mäeorg, U.; Tämm, K.; Burk, P.; Sikk, L.
  • Inglise
ChemCatChem
1867-3899
8
10
2016
18041808
Ilmunud
1.1. Teadusartiklid, mis on kajastatud Web of Science andmebaasides Science Citation Index Expanded, Social Sciences Citation Index, Arts & Humanities Citation Index, Emerging Sources Citation Index ja/või andmebaasis Scopus (v.a. kogumikud)
Ei
SCOPUS

Viited terviktekstile

dx.doi.org/10.1002/cctc.201600176

Lisainfo

Article Mechanism of an efficient and easily applicable catalytic system for the copper(I)-catalyzed azide–alkyne cycloaddition (CuAAC) reaction, consisting of phosphane-ligated CuI carboxylates and apolar/aprotic solvent was investigated by means of 1H NMR reaction monitoring techniques, isotope exchange studies, and DFT calculations (at the M06L/6-311++G(d,p)//B97D/cc-pVDZ (SDD) level of theory). Kinetic analysis indicates 1st order kinetics with respect to [Azide] and nonlinear positive order in [Cu]. H/D scrambling between alkynes reveals a quickly reached equilibrium existing between CuI–carboxylates and CuI–acetylides and that proton transfer processes are mediated by acetate/acetic acid system. According to the computational results, the Cu–triazolide forms a dinuclear structure that equalizes the copper atoms in the catalytic complex.