Helical aromatic urea and guanidine

被引:72
作者
Tanatani, A
Kagechika, H
Azumaya, I
Fukutomi, R
Ito, Y
Yamaguchi, K
Shudo, K
机构
[1] UNIV TOKYO,FAC PHARMACEUT SCI,BUNKYO KU,TOKYO 113,JAPAN
[2] CHIBA UNIV,CTR CHEM ANAL,INAGE KU,CHIBA 263,JAPAN
关键词
D O I
10.1016/S0040-4039(97)00922-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
N,N'-Dimethyl-N,N'-dipheylurea (1) and N,N'-Dimethyl N,N'-diphenylguanidinium bromide (2) each have folded structures with the two phenyl groups located face-to-face. Oligomeric compounds 3 and 4, having five benzene rings connected at the mera positions by cis-urea or guanidino groups, form aromatic layered helices in the crystal state. The crystals are racemic with a I : 1 enantiomer ratio. They exhibit stacked (3) or zigzag chain (4) packing, reflecting displaced parallel structure for the terminal phenyl groups of neighboring molecules of 3 and tilted T-shaped structure for those of 4, respectively. (C) 1997 Elsevier Science.
引用
收藏
页码:4425 / 4428
页数:4
相关论文
共 30 条
[12]   A SELF-ASSEMBLING, HYDROGEN-BONDED HELIX [J].
GEIB, SJ ;
VICENT, C ;
FAN, E ;
HAMILTON, AD .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1993, 32 (01) :119-121
[13]   NOVEL MOLECULAR SCAFFOLDS - FORMATION OF HELICAL SECONDARY STRUCTURE IN A FAMILY OF OLIGOANTHRANILAMIDES [J].
HAMURO, Y ;
GEIB, SJ ;
HAMILTON, AD .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1994, 33 (04) :446-448
[14]   MOLECULAR RECOGNITION AND SELF-ASSEMBLY BY WEAK HYDROGEN-BONDING - UNPRECEDENTED SUPRAMOLECULAR HELICATE STRUCTURES FROM DIAMINE/DIOL MOTIFS [J].
HANESSIAN, S ;
GOMTSYAN, A ;
SIMARD, M ;
ROELENS, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (10) :4495-4496
[15]   POTENTIAL-ENERGY SURFACE OF THE BENZENE DIMER - AH INITIO THEORETICAL-STUDY [J].
HOBZA, P ;
SELZLE, HL ;
SCHLAG, EW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (08) :3500-3506
[16]   CYCLOPHANES .37. STRAIN-ACTIVATED FORMATION OF A TRIPLE-LAYERED PHANE [J].
HOPF, H ;
WITULSKI, B ;
BUBENITSCHEK, P ;
JONES, PG .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1992, 31 (08) :1073-1074
[17]   PREFERENCE OF CIS-AMIDE STRUCTURE IN N-ACYL-N-METHYLANILINES [J].
ITAI, A ;
TORIUMI, Y ;
SAITO, S ;
KAGECHIKA, H ;
SHUDO, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (26) :10649-10650
[18]   AROMATIC AROMATIC INTERACTIONS - FREE-ENERGY PROFILES FOR THE BENZENE DIMER IN WATER, CHLOROFORM, AND LIQUID BENZENE [J].
JORGENSEN, WL ;
SEVERANCE, DL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (12) :4768-4774
[19]  
Kagechika H, 1996, CHEM PHARM BULL, V44, P460
[20]  
Lehn J., 1995, SUPRAMOLECULAR CHEM, V1st