An amide-linked ferrocene dimer, [(CH3CONHC5H4)Fe(C5H4CONHC5H4)Fe(C5H4CONHCH3)].: Formation of inter- and intramolecular NH•••O=C hydrogen bonds

被引:80
作者
Okamura, TA [1 ]
Sakauye, K [1 ]
Ueyama, N [1 ]
Nakamura, A [1 ]
机构
[1] Osaka Univ, Grad Sch Sci, Dept Macromol Sci, Toyonaka, Osaka 5600043, Japan
关键词
D O I
10.1021/ic9806939
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
An amide-linked ferrocene dimer, [(CH3CONHC5H4)Fe(C5H4CONHC5H4)Fe(C5H4CONHCH3)] (7), and a monomer, [(CH3CONHC5H4)Fe(C5H4CONHCH3)] (5), were synthesized, and their unique structures were determined by X-ray analysis. Amide planes are stacked with respect to each other in both crystal and dilute solution. These complexes form intermolecular NH ... O=C hydrogen bonds in the crystal. On the other hand, they form intramolecular NH ... O=C hydrogen bonds in a dilute solution as established by IR and H-1 NMR measurements. Spectral data suggest the presence of flapping structures in solution. Crystal data for 5: triclinic, P (1) over bar, a = 9.358(3) Angstrom, b = 9.947(4) Angstrom, c = 7.946(3) Angstrom, alpha = 106.86(3)degrees, beta = 113.15(3)degrees, gamma = 76.59(3)degrees, V= 644.9(5) Angstrom(3), Z = 2.7(.1)/2EtCN: orthorhombic, Pna(1), a = 7.467(4) Angstrom, b = 14.048(4) Angstrom, c = 23.400(5) Angstrom, Z = 4.
引用
收藏
页码:6731 / 6736
页数:6
相关论文
共 34 条
[1]   Poly(ferrocenylenevinylene) from ring-opening metathesis polymerization of ansa-(vinylene)ferrocene [J].
Buretea, MA ;
Tilley, TD .
ORGANOMETALLICS, 1997, 16 (07) :1507-1510
[2]   The synthesis and characterisation of heterosubstituted aminoferrocenes [J].
Butler, IR ;
Quayle, SC .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1998, 552 (1-2) :63-68
[3]   SYNTHESIS OF 1,1'-BIS(2-AMINO-2-CARBOXYETHYL)FERROCENE (1,1'-FERROCENYLBIS(ALANINE)) [J].
CARLSTROM, AS ;
FREJD, T .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (13) :4175-4180
[4]   TERT-BUTYL-SUBSTITUTED POLY(FERROCENYLENE PERSULFIDES) [J].
COMPTON, DL ;
RAUCHFUSS, TB .
ORGANOMETALLICS, 1994, 13 (11) :4367-4376
[5]   EXCITED-STATES OF MIXED-LIGAND CHELATES OF RUTHENIUM(II) AND RHODIUM(III) [J].
CROSBY, GA ;
ELFRING, WH .
JOURNAL OF PHYSICAL CHEMISTRY, 1976, 80 (20) :2206-2211
[6]   STRUCTURE AND ELECTROCHEMISTRY OF FERROCENYLOLIGOSILANES - ALPHA,OMEGA-BIS(FERROCENYL)OLIGOSILANES AND ALPHA,OMEGA-(1,1'-FERROCENEDIYL)OLIGOSILANES [J].
DEMENTEV, VV ;
CERVANTESLEE, F ;
PARKANYI, L ;
SHARMA, H ;
PANNELL, KH ;
NGUYEN, MT ;
DIAZ, A .
ORGANOMETALLICS, 1993, 12 (05) :1983-1987
[7]  
DERENBERG M, 1971, TETRAHEDRON LETT, V41, P3835
[8]   RING-OPENING POLYMERIZATION OF STRAINED, RING-TILTED [1]FERROCENOPHANES WITH GERMANIUM IN THE BRIDGE - STRUCTURES OF THE [1]GERMAFERROCENOPHANE FE(ETA-C5H4)(2)GEME(2) AND THE FERROCENYLGERMANE FE(ETA-C(5)H(4)ET(2)CL)(ETA-C5H5) [J].
FOUCHER, DA ;
EDWARDS, M ;
BURROW, RA ;
LOUGH, AJ ;
MANNERS, I .
ORGANOMETALLICS, 1994, 13 (12) :4959-4966
[9]   RING-OPENING POLYMERIZATION OF STRAINED, RING-TILTED FERROCENOPHANES - A ROUTE TO HIGH-MOLECULAR-WEIGHT POLY(FERROCENYLSILANES) [J].
FOUCHER, DA ;
TANG, BZ ;
MANNERS, I .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (15) :6246-6248
[10]   ACETYLATION OF SOME SUBSTITUTED FERROCENES [J].
HALL, DW ;
RICHARDS, JH .
JOURNAL OF ORGANIC CHEMISTRY, 1963, 28 (06) :1549-&