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“Tail–Tail Dimerization” of Ferrocene Amino Acid Derivatives
Author(s) -
Siebler Daniel,
Förster Christoph,
Heinze Katja
Publication year - 2010
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.201000384
Subject(s) - chemistry , moiety , intramolecular force , hydrogen bond , ferrocene , intermolecular force , ring (chemistry) , crystal structure , molecule , carbamate , stereochemistry , carboxylic acid , crystallography , electrochemistry , polymer chemistry , organic chemistry , electrode
Acid anhydrides of N‐protected 1′‐aminoferrocene‐1‐carboxylic acid (Fca) have been prepared and spectroscopically characterized (protection group Boc, Fmoc, Ac; 4a – 4c ). The structure of the Boc‐derivative 4a has been determined by single‐crystal X‐ray crystallography. An intramolecular N–H ··· O hydrogen bond involving the carbamate units results in a ring structure containing the two ferrocene units, the anhydride moiety, and the hydrogen bond. In the crystal, the individual molecules are connected by intermolecular N–H ··· O hydrogen bonds of the carbamate unit. Experimental and theoretical studies suggest that the ring motif is also a dominant species in solution. Electronic communication across the anhydride moiety is found to be very weak as judged from electrochemical, spectroscopic, and theoretical experiments.