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Designing Multistep Transformations Using the Hammett Equation:  Imine Exchange on a Copper(I) Template

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Contribution from the Department of Organic Chemistry, University of Geneva, 30 Quai Ernest Ansermet, 1211 Genève 4, Switzerland
Cite this: J. Am. Chem. Soc. 2006, 128, 30, 9887–9892
Publication Date (Web):July 7, 2006
https://doi.org/10.1021/ja061841u
Copyright © 2006 American Chemical Society

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    Herein, we quantify how imine exchange may be used to selectively transform one metallo−organic structure into another. A series of imine exchange reactions were studied, involving a set of 4-substituted anilines, their 2-pyridylimines and 1,10-phenanthrolyl-2,9-diimines, as well as the copper complexes of these imine ligands. Electron-rich anilines were found to displace electron-poor anilines in all cases. Linear free energy relationships (LFERs) were discovered connecting the electron-donating or -withdrawing character of the 4-substituent of an aniline, as measured by the Hammett σpara parameter, to that aniline's ability to compete with unsubstituted aniline to form imines. The quality of these LFERs allowed for quantitative predictions:  to obtain the desired degree of selectivity in an imine exchange between anilines A and B, the required σpara differential could be predicted using a variant of the Hammett equation, log(KAB) = ρ(σA − σB). We validated this methodology by designing and executing a three-step transformation of a series of copper(I)-containing structures. Each step proceeded in predictably high yield, as calculated from σ differentials. At each step in the series of transformations, macrocyclic structures could be created or destroyed through the selection of mono- or di-amines as subcomponents. The same methodology could be used to predict the formation of a diverse dynamic library of helicates from a set of four aniline precursors, as well as the collapse of this library into one helicate upon the addition of a fifth aniline.

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    Characterization data for copper(I) complexes of all of the 2-pyridylimine complexes derived from the 4-substituted anilines studied, details as to the determination of equilibrium constants, and a table of the data used for the Hammett plots of Figures 1 and 2. This material is available free of charge via the Internet at http://pubs.acs.org.

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