The kinetics of methanolysis of a number of esters endowed with a carboxylate anchoring group have been investigated in the presence of di- and trinuclear Zn2+ complexes of calix[4]arenes functionalized at the upper rim with nitrogen ligands. The results (i) emphasize the importance of a good match between ester size and intermetal distance, (ii) reveal a substrate independent superiority of the 1,2-vicinal dinuclear catalyst 1-Zn-2 to its 1,3-distal regioisomer 2-Zn-2, and (iii) provide further evidence for the concurrence of the three metal ions of 3-Zn-3 in the catalytic mechanism.
Cacciapaglia, R., Casnati, A., Mandolini, L., Reinhoudt, D.n., Salvio, R., Sartori, A., et al. (2005). Calix[4]arene-based Zn2+ complexes as shape- and size-selective catalysts of ester cleavage. JOURNAL OF ORGANIC CHEMISTRY, 70(14), 5398-5402 [10.1021/jo050196r].
Calix[4]arene-based Zn2+ complexes as shape- and size-selective catalysts of ester cleavage
Salvio R.;
2005-01-01
Abstract
The kinetics of methanolysis of a number of esters endowed with a carboxylate anchoring group have been investigated in the presence of di- and trinuclear Zn2+ complexes of calix[4]arenes functionalized at the upper rim with nitrogen ligands. The results (i) emphasize the importance of a good match between ester size and intermetal distance, (ii) reveal a substrate independent superiority of the 1,2-vicinal dinuclear catalyst 1-Zn-2 to its 1,3-distal regioisomer 2-Zn-2, and (iii) provide further evidence for the concurrence of the three metal ions of 3-Zn-3 in the catalytic mechanism.| File | Dimensione | Formato | |
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