The influence of constitutional isomerism and change on molecular recognition processes

Chemistry : a European Journal
Avril R WilliamsDavid J Williams

Abstract

Three constitutionally isomeric bis(naphthylmethyl)ammonium ions, in which the two naphthyl groups are substituted 1) both at their 1-positions, 2) one at its 1-position and the other at its 2-position, and 3) both at their 2-positions, have been investigated separately in solution for their propensities to undergo spontaneous self-assembly with three different [24]crown-8 derivatives, namely, pyrido[24]crown-8 (P24C8), dipyrido[24]crown-8 (DP24C8) and dibenzo[24]crown-8 (DB24C8), in turn to form [2]pseudorotaxanes. The strengths of the 1:1 complexes depend on the composition of the secondary dialkylammonium ions and on the nature of the crown ether hosts; generally, as far as the guest cation is concerned, the 1/1- and 2/2-isomers form stronger complexes, as indicated by stability constant measurements, than the 1/2-isomer and, as far as the crown ethers are concerned, the more flexible P24C8 is a much more efficient host than either DP24C8 or DB24C8. The rates of formation of the [2]pseudorotaxanes are fast (i.e., taking no more than a few minutes) in solution with the exception of one case, that is, in which the crown ether host is DB24C8 and the guest cation is the 1/1-isomer, when it can take upwards of one month for the c...Continue Reading

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Citations

Feb 23, 2007·The Journal of Chemical Physics·Yu LiuGe Wang
Dec 29, 2007·Angewandte Chemie·Xingwang Wang, Benjamin List
Dec 7, 2005·Chemistry : a European Journal·Matthias LobertFrank-Gerrit Klärner
Jan 5, 2006·Organic & Biomolecular Chemistry·Pierre MobianJérôme Lacour
Oct 19, 2013·Chemical Communications : Chem Comm·Yasuyuki YamadaKentaro Tanaka
Dec 3, 2011·Angewandte Chemie·Yasuyuki YamadaKentaro Tanaka
Jul 14, 2006·Organic Letters·Thoi D NguyenJeffrey I Zink

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