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首页> 外文期刊>European journal of organic chemistry >Neutral and Ionic Supramolecular Structures of Unsaturated Dicarboxylic Acids and Acridine:Significance of Molecular Geometry and Proton Transfer
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Neutral and Ionic Supramolecular Structures of Unsaturated Dicarboxylic Acids and Acridine:Significance of Molecular Geometry and Proton Transfer

机译：不饱和二羧酸和A啶的中性和离子超分子结构：分子几何学和质子转移的意义

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摘要

Six supramolecular structures exhibiting distinct architectures have been prepared from acridine and different dicarboxylic acids.The co-crystallization of acridine(1)and con-figurational isomers of dicarboxylic acids such as cis,trans-muconic(a)and trans.trans-muconic acid(b),or fumaric(c)and maleic acid(d)provided strikingly different packing motifs and properties.The supramolecular structures have been rationalized based on the molecular geometry and the constituent synthons.Co-crystallization of acridine and b,c,or terephthalic acid(e)gave neutral assemblies stabilized by the O-H...N hydrogen-bond synthon I.Acridine was found to undergo proton transfer with a,d,and acetylenedicarbox-ylic acid(f)to form ionic supramolecular structures exhibiting synthon II,i.e.charge-assisted carboxylate-acridinium O~-...H-N~+-hydrogen bonding.The packing mode of l~+(center dot)a~-has been inferred from the corresponding acridine-isophthalic acid analog based on the superimposable structure of the ac-ids and the common charge-assisted hydrogen bonding motif.Acetylenedicarboxylic and cis.frcms-muconic acid favor the formation of aatiparallel acridinium K-stacks stabilized by alternating hydrogen bonds with two infinite anionic chains of dicarboxylic acids that also undergo head-to-tail hydrogen bonding.Because of their different structure and geometry,b,c,d,and e form less uniform packing arrangements with 1.Fumaric and trans,trans-muconic acid afford 2:1 neutral co-crystals with parallel acridine rings that are stabilized by pi-pi-interactions,whereas terephthalic acid favors association of antiparallel acridine dimers to adopt a different one-dimensional network.By contrast,d undergoes intramolecular hydrogen bonding which leaves only one carboxyl group available to form a 1:1 ionic supramolecular structure with 1.
机译：由a啶和不同的二羧酸制备了六种具有不同结构的超分子结构..啶（1）与二羧酸的构型异构体如顺式，反式-粘康酸（a）和反式-反式粘康酸共结晶（b）或富马酸（c）和马来酸（d）提供了截然不同的堆积图案和特性。已根据分子几何结构和合成子对超分子结构进行了合理化。a啶和b，c，or的共结晶对苯二酸通过OH ... N氢键合成子I稳定中性组装。发现A啶与a，d和乙炔化的羧酸（f）进行质子转移，形成显示合成子II的离子超分子结构，即电荷辅助的羧酸-基O〜-... HN〜+-氢键。从相应的a啶-间苯二甲酸类似物的可叠加性推导了l〜+（中心点）a〜的堆积方式。一个的结构c-ids和常见的电荷辅助氢键基序。乙炔二羧酸和顺式frcms-粘康酸有助于通过平行的氢键与二元羧酸的两个无限阴离子链交替进行氢键稳定而形成a啶K啶酮叠层尾部氢键。由于它们的结构和几何形状不同，b，c，d和e与1.形成较不均匀的堆积排列。富马酸和反式，反式-粘康酸可提供2：1的中性共晶体和平行的a啶环通过pi-pi相互作用稳定，而对苯二甲酸则有利于反平行a啶二聚体的缔合以采用不同的一维网络。相反，d经历分子内氢键键合，仅留下一个羧基可用于形成1：1离子超分子结构与1。

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