Is [N+-H...O] hydrogen bonding the most important noncovalent interaction in macrocycle-dibenzylammonium ion complexes?

The Journal of Organic Chemistry
Pin-Nan ChengSheng-Hsien Chiu

Abstract

We report a new host molecule in which one diethylene glycol chain (i.e., a loop possessing only three oxygen atoms) incorporated along with two phenolic aromatic rings is linked by a xylene spacer into a macroring. The design of the molecular structure of this macrocycle "amplifies" any potential [cation...pi], [N+-H...pi], and [N+C-H...pi] interactions between the dibenzylammonium (DBA+) ion and the phenolic rings of the macrocycle; as such, these species display a very strong binding affinity in CD3NO2 (Ka = 15,000 M(-1)). The macroring also coordinates to bipyridinium ions in a [2]pseudorotaxane fashion, which makes it the smallest macrocycle (i.e., a 25-membered ring) known to complex both DBA+ and bipyridinium ions in solution. To confirm unambiguously that these pseudorotaxanes exist in solution, we synthesized their corresponding interlocked molecules, namely rotaxanes and catenanes.

Citations

Sep 30, 2006·Chemical Communications : Chem Comm·Kuang-Wei ChengSheng-Hsien Chiu
Jan 24, 2008·Chemistry : a European Journal·Nai-Chia ChenSheng-Hsien Chiu
Apr 30, 2008·Angewandte Chemie·Sheng-Yao HsuehSheng-Hsien Chiu
May 10, 2008·Physical Chemistry Chemical Physics : PCCP·Seiji Tsuzuki, Asuka Fujii
Jul 18, 2009·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Weidong ZhouYuliang Li
May 8, 2010·Chemistry : a European Journal·Jia-Ling KoSheng-Hsien Chiu
Feb 7, 2008·Chemical Communications : Chem Comm·Shau-Hua UengSheng-Hsien Chiu
May 17, 2013·Chemistry : a European Journal·Liang-Yun WangSheng-Hsien Chiu
Nov 10, 2013·Chemistry : a European Journal·Ji-Na ZhangHe Tian
Dec 25, 2008·Organic Letters·Tzu-Chiun LinSheng-Hsien Chiu
Jul 10, 2012·Journal of the American Chemical Society·Zhixue ZhuJ Fraser Stoddart
Nov 14, 2012·Chemical Reviews·A Subha Mahadevi, G Narahari Sastry

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