Ferrocene compounds. XXXVIII. Dimethyl ferrocene-1,1′-dicarboxylate

Abstract

In the title compound, [Fe(C(7)H(7)O(2))(2)], the cyclopentadienyl rings and the two attached methoxycarbonyl groups, in an anti arrangement, form an extended pi-conjugated system. The Fe-C distances range from 2.035 (3) to 2.061 (3) A and the average value of the C-C bond lengths in the two cyclopentadienyl rings is 1.419 (5) A. The rings are almost parallel to one another [1.0 (2) degrees ] and are mutually twisted from an eclipsed conformation by only 1.8 (3) degrees (average value). The methoxycarbonyl groups are twisted out of the plane of the cyclopentadienyl rings by 6.5 (4) and 15.7 (4) degrees, respectively. The molecules are joined into dimers by intermolecular C-H.O hydrogen bonds that form ten-membered rings. The same types of hydrogen bonds form eight-membered rings and infinite chains along the b axis.

Synthesis, Structure, Electrochemistry, and Cytotoxic Properties of Ferrocenyl Ester Derivatives

“…While the solid structure of Fe(C 5 H 4 CO 2 CH 3 ) 2 has been reported previously, our solid-state structure has a fundamental difference to that published by Cetina et al [22]. That is, in the lattice, they determined a hydrogen bonding network between the carbonyl group and the CH 3 of the adjacent molecule.…”

Polysubstituted ferrocenes as tunable redox mediators

“…DFT calculations (B3LYP, def2-TZVP, RIJCOSX, ZORA, CPCM (CH 2 Cl 2 )) on di-, tri- and tetraesters 2 – 4 suggest an intramolecular coupling of the C=O vibrations of the ester moieties substantiating the number of observed bands (Table S1, Supporting Information File 1 ). Furthermore, crystal packing effects with intermolecular C=O∙∙∙H–C interactions, differing in strengths, can be responsible for the occurrence of distinguishable C=O bands [ 54 , 76 – 77 ]. For example, two different molecules of monoester 1 are present in the asymmetric unit of the solid-state structure [ 76 ], leading to different C=O stretching vibration bands ( Fig.…”

1′-(1-Hydroxyethyl)-N,N-diphenylferrocene-1-carboxamide

“…The coplanar arrangement of a carbonyl group attached to the ring should allow maximum interaction of the two % systems (Lin et al, 1998). In (III), the C11 O1 bond is twisted out of the C1±C5 ring by 39.3 (3) , and the C1ÐC11 bond is longer than the equivalent bond in our previously reported structures where a carbonyl group is attached to the Cp ring (1.46±1.47 A Ê ; Pavlovic  et al, 2002;Baris Ïic  et al, 2003;Cetina et al, 2003;Pavlovic  et al, 2003). In these, the C11 O1 bond is almost coplanar with the Cp ring.…”