The mechanism of formation of amide-based interlocked compounds: prediction of a new rotaxane-forming motif

Chemistry : a European Journal
David A LeighFrancesco Zerbetto

Abstract

Molecular modeling of four different reagent systems shows that the (free) energies of supramolecular interactions in the gas phase and in solution can explain the different reaction products (i.e., various sized macrocycles, catenanes, and linear oligomers) that are formed in classic amide-catenane-forming reactions. Self-assembly of the catenanes requires the formation of ordered intertwined chains and is driven by bifurcated hydrogen bonds, with pi stacking only playing a lesser role. The understanding gained from the computational study was used to predict the possibility of a new rotaxane-forming system that does not permit catenane formation. The predictions were confirmed by the successful synthesis and characterization (including X-ray crystallography) of two novel rotaxanes.

Citations

Sep 26, 2015·The Journal of Organic Chemistry·Alberto Martinez-CuezvaJose Berna
Jun 21, 2016·Journal of the American Chemical Society·Jamie M CameronLeroy Cronin
Oct 8, 2009·Journal of the American Chemical Society·Stephen M GoldupJhenyi Wu
Jul 11, 2006·Chemistry : a European Journal·Michał J Chmielewski, Janusz Jurczak
Mar 21, 2009·Organic & Biomolecular Chemistry·Ming LiuFeihe Huang
Oct 21, 2009·Chemical Communications : Chem Comm·Jeremiah J GassensmithBradley D Smith
May 17, 2006·Chemical Communications : Chem Comm·Paul D BeerDavid Curiel
Apr 11, 2006·Organic & Biomolecular Chemistry·Mark R SambrookJames A Wisner
Apr 1, 2006·Chemistry : a European Journal·Easwaran ArunkumarBradley D Smith
Apr 17, 2019·Chemistry : a European Journal·Rafał OrłowskiDaniel T Gryko
Jan 30, 2020·Chemistry : a European Journal·Masahide TominagaKentaro Yamaguchi
May 8, 2015·Angewandte Chemie·Guzmán Gil-RamírezAlexander J Stephens
May 1, 2015·Chemical Science·Alberto Martinez-CuezvaJose Berna
Jul 24, 2012·Dalton Transactions : an International Journal of Inorganic Chemistry·Cristina AlvariñoJosé M Quintela
Jun 18, 2010·Journal of the American Chemical Society·Daniel M D'SouzaSongwei Zhang
Apr 11, 2009·The Journal of Physical Chemistry. B·Ganga PeriyasamyFrançoise Remacle
Apr 29, 2011·The Journal of Physical Chemistry. a·Anouk M RijsWybren Jan Buma
Jul 2, 2011·Journal of the American Chemical Society·Rehan AhmedJ Derek Woollins
Mar 21, 2018·Journal of the American Chemical Society·James E M LewisStephen M Goldup
Mar 31, 2006·The Journal of Physical Chemistry. B·Guang-Fu YangChang-Guo Zhan
Mar 10, 2005·Journal of the American Chemical Society·Easwaran ArunkumarBradley D Smith

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