Crystal structure of methyl ferrocenemonocarboxylate, [Fe(C5H5)(C5H4C2O2H3)]

Beck, W.; Woisetschläger, Oliver E.; Mayer, Péter

doi:10.1524/ncrs.2001.216.14.425

Cited by 3 publications

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“…The values of the bond angles in the Cp rings are in the range 106.9 (3)±109.3 (3) . The structural parameters are consistent with those of similar structures that have a methoxycarbonyl group on one of the Cp rings (Luo et al, 1990;Podlaha et al, 1996;Hobi et al, 1997;Beck et al, 2001;Costa et al, 2001) and with the structure of methyl 3-ferrocenylpropanoate (Cetina et al, 2002). Selected geometric parameters for (I) are listed in Table 1.…”

Section: Figuresupporting

confidence: 79%

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

et al. 2003

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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.

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Section: Figuresupporting

confidence: 79%

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

et al. 2003

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“…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.…”

Section: Resultsmentioning

confidence: 99%

“…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. 3 ).…”

Section: Resultsmentioning

confidence: 99%

Polysubstituted ferrocenes as tunable redox mediators

Waniek¹,

Klett²,

Förster³

et al. 2018

Beilstein J. Org. Chem.

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A series of four ferrocenyl ester compounds, 1-methoxycarbonyl- (1), 1,1’-bis(methoxycarbonyl)- (2), 1,1’,3-tris(methoxycarbonyl)- (3) and 1,1’,3,3’-tetrakis(methoxycarbonyl)ferrocene (4), has been studied with respect to their potential use as redox mediators. The impact of the number and position of ester groups present in 1–4 on the electrochemical potential E 1/2 is correlated with the sum of Hammett constants. The 1/1 +–4/4 + redox couples are chemically stable under the conditions of electrolysis as demonstrated by IR and UV–vis spectroelectrochemical methods. The energies of the C=O stretching vibrations of the ester moieties and the energies of the UV–vis absorptions of 1–4 and 1 +–4 + correlate with the number of ester groups. Paramagnetic 1H NMR redox titration experiments give access to the chemical shifts of 1 +–4 + and underline the fast electron self-exchange of the ferrocene/ferrocenium redox couples, required for rapid redox mediation in organic electrosynthesis.

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“…The angles between the least-square plane of O1, O2, C6, C7, and C8 and the C 5H5 units are 9.58(13)°and 10.22(17) Å, respectively, indicating slight deviation from coplanarity. A stronger deviation is found in methyl ferrocenemonocarboxylate [3] for the ester and C 5 H 5 units (13.07 (18) …”

Section: Discussionmentioning

confidence: 96%

Crystal structure of 1,6-di(ferrocenyl)-3,4-dihydroxy-hexa-2,4-diene- 1,6-dion, Fe2(C5H5)2(C16H12O4)

Mayer

Woisetschläger²,

Beck

2002

Zeitschrift Für Kristallographie - New Crystal Structures

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Source of materialThe title complex was synthesized from acetylferrocene, potassium hydride and diethyloxalate in thf, as described in [1]. Violet plates were obtained from a concentrated solution of the title compound in dichloromethane. DiscussionThe title molecule Fe 2(C5H5)2(C16H12O4) 1 possesses an inversion centre (figure). The bond lengths and bond angles clearly show that the title complex has also in the solid state the keto enol structure and that the two hydroxy groups are in 3,4 positions of the hexadiene-dion rather than in 1,6. Important bond lengths and bond angles are:The bond lengths in 1 are very similar to those in a bis(palladium) complex of the dianion of 1-with the exception that in that complex the four C-O distances are almost identical (1.282(4) Å, 1.279(4) Å), as expected. In the structure of 1, there is no symmetrical hydrogen bridge between the carbonyl groups. The bond length of O2-H82 is 0.88(3) Å while the distance between H82 and the acceptor O1 is 1.70(3) Å. The bond angle ÐO2-H82-O1 is 155(3)°. The angles between the least-square plane of O1, O2, C6, C7, and C8 and the C 5H5 units are 9.58 (13)

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Crystal structure of methyl ferrocenemonocarboxylate, [Fe(C5H5)(C5H4C2O2H3)]

Cited by 3 publications

References 0 publications

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

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

Polysubstituted ferrocenes as tunable redox mediators

Crystal structure of 1,6-di(ferrocenyl)-3,4-dihydroxy-hexa-2,4-diene- 1,6-dion, Fe2(C5H5)2(C16H12O4)

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