Main chain ferrocenyl amides from 1-aminoferrocene-1′-carboxylic acid

被引：116

作者：

Heinze, K ^{[1
]}

Schlenker, M ^{[1
]}

机构：

[1] Heidelberg Univ, Inst Anorgan Chem, D-69120 Heidelberg, Germany

来源：

EUROPEAN JOURNAL OF INORGANIC CHEMISTRY | 2004年 / 14期

关键词：

metallocenes; hydrogen bonds; peptides; conformation analysis;

D O I：

10.1002/ejic.200300897

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The non-natural amino acid 1-aminoferrocene-1'-carboxylic acid is synthesised from ferrocene in eight steps. The folding and association phenomena of amido-substituted ferrocenes in the crystal as well as in solution are studied by X-ray crystallography, IR and NMR spectroscopy and DFT calculations. The amino acid is selectively protected at the amino group with the use of the fluorenyl-9-methoxycarbonyl (Fmoc) group. An amide-linked ferrocene dimer is prepared using the HOBt/DCC protocol for amide formation. In the crystal the dimer forms a hydrogen-bonded sheet structure, while in solution dynamic intramolecular hydrogen bonds are observed by VT H-1 NMR and IR spectroscopy. The dynamic flipping process has been rationalised by DFT calculations. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004).

引用

页码：2974 / 2988

页数：15

共 57 条

[1] SOME NITROGEN-CONTAINING FERROCENE DERIVATIVES [J].