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.
Calix[4]arene-Based Zn2+ Complexes as Shape and Size Selective Catalysts of Ester Cleavage / Cacciapaglia, R.; Casnati, Alessandro; Mandolini, L.; Reinhoudt, D. N.; Salvio, R.; Sartori, Andrea; Ungaro, Rocco. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 70:(2005), pp. 5398-5402. [10.1021/jo050196r]
Calix[4]arene-Based Zn2+ Complexes as Shape and Size Selective Catalysts of Ester Cleavage
CASNATI, Alessandro;SARTORI, Andrea;UNGARO, Rocco
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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