Calix(4)arene-based Zn2+ complexes as shape- and size-selective catalysts of ester cleavage

Roberta Cacciapaglia; Alessandro Casnati; Luigi Mandolini; David Reinhoudt; R. Salvio; Riccardo Salvio; A. Sartori; Rocco Ungaro

doi:10.1021/jo050196r

Calix(4)arene-based Zn2+ complexes as shape- and size-selective catalysts of ester cleavage

Roberta Cacciapaglia, Alessandro Casnati, Luigi Mandolini, David Reinhoudt, R. Salvio, Riccardo Salvio, A. Sartori, Rocco Ungaro

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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-Zn2 to its 1,3-distal regioisomer 2-Zn2, and (iii) provide further evidence for the concurrence of the three metal ions of 3-Zn3 in the catalytic mechanism.

Original language	Undefined
Pages (from-to)	5398-5402
Journal	The journal of organic chemistry
Volume	70
Issue number	14
DOIs	https://doi.org/10.1021/jo050196r
Publication status	Published - 2005

Keywords

METIS-225114
IR-53008

Access to Document

10.1021/jo050196r

Cite this

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title = "Calix(4)arene-based Zn2+ complexes as shape- and size-selective catalysts of ester cleavage",

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-Zn2 to its 1,3-distal regioisomer 2-Zn2, and (iii) provide further evidence for the concurrence of the three metal ions of 3-Zn3 in the catalytic mechanism.",

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year = "2005",

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language = "Undefined",

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pages = "5398--5402",

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publisher = "American Chemical Society",

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TY - JOUR

T1 - Calix(4)arene-based Zn2+ complexes as shape- and size-selective catalysts of ester cleavage

AU - Cacciapaglia, Roberta

AU - Casnati, Alessandro

AU - Mandolini, Luigi

AU - Reinhoudt, David

AU - Salvio, R.

AU - Salvio, Riccardo

AU - Sartori, A.

AU - Ungaro, Rocco

PY - 2005

Y1 - 2005

N2 - 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-Zn2 to its 1,3-distal regioisomer 2-Zn2, and (iii) provide further evidence for the concurrence of the three metal ions of 3-Zn3 in the catalytic mechanism.

AB - 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-Zn2 to its 1,3-distal regioisomer 2-Zn2, and (iii) provide further evidence for the concurrence of the three metal ions of 3-Zn3 in the catalytic mechanism.

KW - METIS-225114

KW - IR-53008

U2 - 10.1021/jo050196r

DO - 10.1021/jo050196r

M3 - Article

SN - 0022-3263

VL - 70

SP - 5398

EP - 5402

JO - The journal of organic chemistry

JF - The journal of organic chemistry

IS - 14

ER -