Copper(i)-induced amplification of a [2]catenane in a virtual dynamic library of macrocyclic alkenes

J.A. Berrocal, M.M.L. Nieuwenhuizen, L. Mandolini, E.W. Meijer, S. Di Stefano

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Abstract

Olefin cross-metathesis of diluted dichloromethane solutions (=0.15 M) of the 28-membered macrocyclic alkene C1, featuring a 1,10-phenanthroline moiety in the backbone, as well as of catenand 1, composed of two identical interlocked C1 units, generates families of noninterlocked oligomers Ci. The composition of the libraries is strongly dependent on the monomer concentration, but independent of whether C1 or 1 is used as feedstock, as expected for truly equilibrated systems. Accordingly, the limiting value 0.022 M approached by the equilibrium concentration of C1 when the total monomer concentration approaches the critical value, as predicted by the Jacobson-Stockmayer theory, provides a reliable estimate of the thermodynamically effective molarity. Catenand 1 behaves as a virtual component of the dynamic libraries, in that there is no detectable trace of its presence in the equilibrated mixtures, but becomes the major component-in the form of its copper(i) complex-when olefin cross-metathesis is carried out in the presence of a copper(i) salt. This journal is © the Partner Organisations 2014.
Original languageEnglish
Pages (from-to)6167-6174
Number of pages8
JournalOrganic & Biomolecular Chemistry
Volume12
Issue number32
DOIs
Publication statusPublished - 2014

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Digital Libraries
Alkenes
alkenes
Amplification
Copper
metathesis
copper
Libraries
monomers
Monomers
Methylene Chloride
oligomers
Oligomers
Feedstocks
Salts
salts
estimates
Chemical analysis
catenane

Cite this

Berrocal, J.A. ; Nieuwenhuizen, M.M.L. ; Mandolini, L. ; Meijer, E.W. ; Di Stefano, S. / Copper(i)-induced amplification of a [2]catenane in a virtual dynamic library of macrocyclic alkenes. In: Organic & Biomolecular Chemistry. 2014 ; Vol. 12, No. 32. pp. 6167-6174.
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abstract = "Olefin cross-metathesis of diluted dichloromethane solutions (=0.15 M) of the 28-membered macrocyclic alkene C1, featuring a 1,10-phenanthroline moiety in the backbone, as well as of catenand 1, composed of two identical interlocked C1 units, generates families of noninterlocked oligomers Ci. The composition of the libraries is strongly dependent on the monomer concentration, but independent of whether C1 or 1 is used as feedstock, as expected for truly equilibrated systems. Accordingly, the limiting value 0.022 M approached by the equilibrium concentration of C1 when the total monomer concentration approaches the critical value, as predicted by the Jacobson-Stockmayer theory, provides a reliable estimate of the thermodynamically effective molarity. Catenand 1 behaves as a virtual component of the dynamic libraries, in that there is no detectable trace of its presence in the equilibrated mixtures, but becomes the major component-in the form of its copper(i) complex-when olefin cross-metathesis is carried out in the presence of a copper(i) salt. This journal is {\circledC} the Partner Organisations 2014.",
author = "J.A. Berrocal and M.M.L. Nieuwenhuizen and L. Mandolini and E.W. Meijer and {Di Stefano}, S.",
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Copper(i)-induced amplification of a [2]catenane in a virtual dynamic library of macrocyclic alkenes. / Berrocal, J.A.; Nieuwenhuizen, M.M.L.; Mandolini, L.; Meijer, E.W.; Di Stefano, S.

In: Organic & Biomolecular Chemistry, Vol. 12, No. 32, 2014, p. 6167-6174.

Research output: Contribution to journalArticleAcademicpeer-review

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T1 - Copper(i)-induced amplification of a [2]catenane in a virtual dynamic library of macrocyclic alkenes

AU - Berrocal, J.A.

AU - Nieuwenhuizen, M.M.L.

AU - Mandolini, L.

AU - Meijer, E.W.

AU - Di Stefano, S.

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AB - Olefin cross-metathesis of diluted dichloromethane solutions (=0.15 M) of the 28-membered macrocyclic alkene C1, featuring a 1,10-phenanthroline moiety in the backbone, as well as of catenand 1, composed of two identical interlocked C1 units, generates families of noninterlocked oligomers Ci. The composition of the libraries is strongly dependent on the monomer concentration, but independent of whether C1 or 1 is used as feedstock, as expected for truly equilibrated systems. Accordingly, the limiting value 0.022 M approached by the equilibrium concentration of C1 when the total monomer concentration approaches the critical value, as predicted by the Jacobson-Stockmayer theory, provides a reliable estimate of the thermodynamically effective molarity. Catenand 1 behaves as a virtual component of the dynamic libraries, in that there is no detectable trace of its presence in the equilibrated mixtures, but becomes the major component-in the form of its copper(i) complex-when olefin cross-metathesis is carried out in the presence of a copper(i) salt. This journal is © the Partner Organisations 2014.

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