N-Methylated Diphenylguanidines: Conformations, Propeller-Type Molecular Chirality, and Construction of Water-Soluble Oligomers with Multilayered Aromatic Structures
N-Methylated Diphenylguanidines: Conformations, Propeller-Type Molecular Chirality, and Construction of Water-Soluble Oligomers with Multilayered Aromatic Structures
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N-甲基化二苯胍：构象、螺旋桨型分子手性以及具有多层芳香结构的水溶性低聚物的构建
DOI：
10.1021/ja9806534
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发表时间：
1998
影响因子：
15
通讯作者：
H. Kagechika
中科院分区：
文献类型：
--
作者：
Aya Tanatani;K. Yamaguchi;I. Azumaya;R. Fukutomi;K. Shudo;H. Kagechika
本文研究了N，N '-二苯基胍（1）及其N-甲基化衍生物的晶体结构，并利用它们的构象特性构建了具有多层芳香结构的水溶性低聚物。N，N '-二苯基胍（1）在乙醇中重结晶后得到两种类型的晶体，手性（P212121）和外消旋（P21/c）。在这两种晶体中，1都以（E，Z）构象存在，其中一个连接到苯环上的C-N键（长度：1.28 - 1.30 A）显示双键特征。相比之下，N，N '-二甲基-N，N'-二苯基胍（4a）以两个芳环彼此面对的（Z，Z）构象存在。从几种N-甲基化化合物的晶体结构判断，二苯基胍的构象偏好似乎与芳族苯胺的构象偏好有关。N，N，N ′，N ″-四甲基-N ′，N ″-二苯基胍碘化物（6）得到手性晶体1和N-甲基-N，N ′-二苯基胍（2）。每个对映体的绝对结构...
The crystal structures of N,N‘-diphenylguanidine (1) and its N-methylated derivatives were investigated, and the conformational properties of these molecules were utilized to construct water-soluble oligomers with multilayered aromatic structures. N,N‘-Diphenylguanidine (1) afforded two types of crystals, chiral (P212121) and racemic (P21/c), upon recrystallization from EtOH. In both crystals, 1 exists in the (E,Z) conformation, in which one C−N bond (length: 1.28−1.30 A) attached to a phenyl ring shows double-bond character. In contrast, N,N‘-dimethyl-N,N‘-diphenylguanidine (4a) exists in the (Z,Z) conformation with the two aromatic rings facing each other. As judged from the crystal structures of several N-methylated compounds, the conformational preferences of diphenylguanidines appear to be related to those of aromatic anilides. N,N,N‘,N‘‘-Tetramethyl-N‘,N‘‘-diphenylguanidinium iodide (6) afforded chiral crystals, like 1 and N-methyl-N,N‘-diphenylguanidine (2). The absolute structure of each enantiom...