Intramolecular C—H...O and intermolecular N—H...O and C—H...O interactions in<i>N</i>-ferrocenoylglycine benzyl ester, an effective dihydrogen phosphate anion sensing agent

Gallagher, John F.; Kenny, Peter T.M.; Sheehy, Michael J.

doi:10.1107/s010827019900520x

Cited by 4 publications

(5 citation statements)

References 8 publications

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“…Relevant geometric data are given in Table . The overall molecular geometries compare favorably with those of Hdpf, its P-chalcogen derivatives, , and the related ferrocenecarboxylic derivatives: FcCONHCH 2 CO 2 R (R = Me and CH 2 Ph; Fc = ferrocenyl) and fc(CONHCH 2 CONH 2 ) 2 ·2H 2 O (fc = ferrocene-1,1′-diyl) …”

Section: Resultsmentioning

confidence: 87%

Phosphinoferrocenyl Carboxamides Bearing Glycine Pendant Groups: Synthesis, Palladium(II) Complexes, and Catalytic Use in Polar and Aqueous Reaction Media

2009

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The reaction of 1′-(diphenylphosphino)-1-ferrocenecarboxylic acid (Hdpf) with H2NCH2CO2CR3 mediated by peptide coupling agents (EDC/HOBt) afforded novel glycine phosphino-carboxamides Ph2PfcCONHCH2CO2CR3 (fc = ferrocene-1,1′-diyl; R = H (1) and Me (2*)). Compound 1 was converted to its corresponding phosphine oxide (3*) and sulfide (4*), to N-acyl glycine Ph2PfcCONHCH2CO2H (5), and to bis-amide Ph2PfcCONHCH2CONH2 (6*). Compounds 1 and 6 reacted with [PdCl2(cod)] (cod = η2:η2-cycloocta-1,5-diene) and 5 reacted with Na2[PdCl4] to afford the respective, mostly solvated bis-phosphine complexes trans-[PdCl2(L-κP)2] (7: L = 1; 8: L = 5, 9: L = 6). Two different solvatomorphs of 9 were isolated in crystalline form and structurally characterized (9* and 9a*). Furthermore, bridge cleavage reaction of [{Pd(μ-Cl)(LNC)}2] (LNC = 2-[(dimethylamino-κN)methyl]phenyl-κC 1) with 1 gave [(LNC)Pd(Cl)(1-κP)] (10*), which was further reacted with AgClO4 or KOt-Bu to afford bis-chelate complexes [(LNC)Pd(1-κ2 O,P)]ClO4 (11*) and [(LNC)Pd(L-κ2 N,P)] (12*; L = 1 deprotonated at the NH group), respectively. All compounds were characterized by spectroscopic methods (multinuclear NMR, MS, and IR) and by elemental analyses; the asterisk indicates that the crystal structure has been determined. Compounds 1, 3−6, and 10−12 were studied by electrochemical methods, while phosphines 1, 5, and 6 in combination with palladium(II) acetate were shown to be highly active catalysts for the Suzuki−Miyaura cross-coupling of aryl bromides with phenylboronic acid in polar solvents (ethanol and dioxane), in their aqueous mixtures, and in pure water.

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Section: Resultsmentioning

confidence: 87%

Phosphinoferrocenyl Carboxamides Bearing Glycine Pendant Groups: Synthesis, Palladium(II) Complexes, and Catalytic Use in Polar and Aqueous Reaction Media

2009

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“…The molecular structure of 4 can be directly compared with the related glycine ester analogues [14,28], and related derivatives [7,12]. As can be evidenced by analysis of the interplanar angles which are 16.7(2)°and 16.6(2)°in the glycine methyl and benzyl ester derivatives, respectively, the overall molecular conformation is broadly similar in the ferrocenyl amide moieties.…”

Section: X-ray Crystallographic Studies Ofmentioning

confidence: 95%

“…4. The structure can be directly compared with the glycine methyl and benzyl esters that have been communicated previously by the authors [14,28] and related structures that are available in the literature [7,12].…”

Section: X-ray Crystallographic Studies Ofmentioning

confidence: 99%

“…The compounds are reasonably stable however they slowly decompose over a period of time. Crystals suitable for X-ray crystallographic analysis were obtained for compounds 1 [14], 3 [28] and 4. The products were characterised by spectroscopic techniques prior to the electrochemical studies to confirm their structures.…”

Section: Synthesismentioning

confidence: 99%

“…The electrochemical properties of these unnatural amino acid esters as anion receptors has been investigated using a platinum microdisk working microelectrode which represents a relatively new departure from the widespread use of conventional platinum macroelectrodes in metal-organic analytical studies (electrochemical details in experimental). The 1 H NMR anion coordination properties of compounds 1-10 are also reported, and the X-ray crystal structure of N -ferrocenoyl alanine methyl ester 4 has been determined for comparison with related structures [7,12] and the reported N -ferrocenoyl glycine ester derivatives [14,28]. The benefit of such crystal structure analysis is that it can provide an understanding of the possible interactions present in the structure of a potential anion receptor as well as yield valuable information for hydrogen binding modes and binding sites in solution studies.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and structural characterisation of redox-responsive N-ferrocenoyl amino acid esters; the X-ray crystal structure of N-ferrocenoyl alanine methyl ester; electrochemical anion recognition and 1H NMR complexation studies

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Semi-rigid N-para-ferrocenyl(benzoyl)amino-acid esters for biomaterials: synthesis and characterization of Fc-C6H4CONHCH(R)CO2Me where Fc=(η5-C5H5)Fe(η5-C5H4) and R=H, CH3,CH2CH(CH3)2,CH2C6H5 and the X-ray crystal structures of Fc-C6H4CO2Me and the l-alanine derivative Fc-C6H4CONHCH(CH3)CO2Me

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Ida

et al. 2002

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Intramolecular C—H...O and intermolecular N—H...O and C—H...O interactions inN-ferrocenoylglycine benzyl ester, an effective dihydrogen phosphate anion sensing agent

Cited by 4 publications

References 8 publications

Phosphinoferrocenyl Carboxamides Bearing Glycine Pendant Groups: Synthesis, Palladium(II) Complexes, and Catalytic Use in Polar and Aqueous Reaction Media

Phosphinoferrocenyl Carboxamides Bearing Glycine Pendant Groups: Synthesis, Palladium(II) Complexes, and Catalytic Use in Polar and Aqueous Reaction Media

Synthesis and structural characterisation of redox-responsive N-ferrocenoyl amino acid esters; the X-ray crystal structure of N-ferrocenoyl alanine methyl ester; electrochemical anion recognition and 1H NMR complexation studies

Semi-rigid N-para-ferrocenyl(benzoyl)amino-acid esters for biomaterials: synthesis and characterization of Fc-C6H4CONHCH(R)CO2Me where Fc=(η5-C5H5)Fe(η5-C5H4) and R=H, CH3,CH2CH(CH3)2,CH2C6H5 and the X-ray crystal structures of Fc-C6H4CO2Me and the l-alanine derivative Fc-C6H4CONHCH(CH3)CO2Me

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