In this study we synthesized three macrocyclic tetralactams 1, possessing two phenylenedioxydiacetamide units and various spacers, for use as hydrogen bond accepting hosts for mono- and bis-dialkylammonium ions. The cyclic tetralactam 1b, featuring propylene spacers, bound secondary mono- and bis-dialkylammonium ions efficiently to form corresponding pseudo[2]rotaxanes stabilized through hydrogen bonding between the two components. The cyclic tetralactams bearing other spacers (1a and 1d) also bound these dialkylammonium ions, but the macrocycle 1a (ethylene spacer) predominantly constructed a face-to-face complex, while the macrocycle 1d (3-oxypentalene spacer) formed a non-selective complex. We synthesized three [2]rotaxanes, through imine and oxime formation, from pseudo[2]rotaxanes self-assembled from the propylene-spacer tetralactam 1b and mono- and bis-alkylammonium ions. ¹H NMR spectroscopy and X-ray crystallography revealed that hydrogen bonds between the dumbbell-shaped and macrocyclic components restricted the conformation of the amide units in the [2]rotaxanes in solution and in the solid state.

中文翻译：

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包含环苯二氧基二乙酰胺和仲单和双二烷基铵离子的轮烷：大环尺寸对假轮烷形成的影响

在这项研究中，我们合成了三个具有两个苯二氧基二乙酰胺单元和各种间隔基的大环四内酰胺1，用作单-和双-二烷基铵离子的氢键接受主体。具有丙烯间隔基的环状四内酰胺1b有效地结合了仲单-和双-二烷基铵离子，形成了通过两个组分之间的氢键稳定的相应的假[2]轮烷。带有其他间隔基（1a和1d）的环状四内酰胺也结合了这些二烷基铵离子，但大环1a（乙烯间隔基）主要构成了面对面的配合物，而大环1d（3-氧戊烯间隔基）形成非选择性络合物。我们通过亚胺和肟的合成，从由丙烯-间隔四内酰胺1b和单-和双-烷基铵离子自组装的假[2]轮烷中合成了三种[2]轮烷。¹ H NMR谱和X射线晶体学表明，哑铃形和大环组分之间的氢键限制了溶液中和固态的[2]轮烷中酰胺单元的构象。