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

Savage, David; Gallagher, John F.; Ida, Yoshiteru; Kenny, Peter T.M.

doi:10.1016/s1387-7003(02)00638-x

Cited by 28 publications

(46 citation statements)

References 29 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Fragment ions were not observed or were of very low intensity in the MALDI spectra. This is in contrast to the analysis of the related para-ferrocenyl benzoyl amino acid derivatives by FABMS where important fragment ions were observed [28]. The ESI mass spectra displayed [M + H] + species and intense adducts due to sodium and potassium were present 22 and 38 Da higher than the protonated molecular ion species.…”

contrasting

confidence: 73%

“…The 1 H and 13 C NMR spectra for compounds 3-10 showed peaks in the ferrocene region characteristic of a mono substituted ferrocene moiety [11,12,28]. The protons in the ortho position of the (g 5 -C 5 H 4 ) ring appear in the region Table 1.…”

mentioning

confidence: 97%

“…The incorporation of a ferrocene group onto proteins has shown the mediation of electron transfer between electrodes and the protein redox site [3,5]. The synthesis and structural characterization of novel N-ferrocenoyl and N-ferrocenyl amino acid and peptide derivatives has been reported [11][12][13][14][15][16][17][18][19][20][21][22][23][24][25][26][27][28]. The aim of this research is to incorporate three key moieties in the synthesis of unusual biological materials, namely (i) an electroactive core, (ii) a conjugated linker that can act as a chromophore and (iii) an amino acid derivative that can interact with other molecules via hydrogen bonding.…”

mentioning

confidence: 99%

“…In this communication, we report the synthesis and structural characterization of a series of novel Nmeta-ferrocenyl benzoyl amino acid ester derivatives. We recently reported the synthesis and structural characterization of a series of N-para-ferrocenyl benzoyl amino acid ester derivatives [28] and the N-ortho-ferrocenyl benzoyl amino acid derivatives will be reported in due course.The meta-ferrocenyl benzoic acid 2 was prepared using conventional diazonium salt chemistry. Treatment of ethyl-3-aminobenzoate with sodium nitrite in the presence of hydrochloric acid yielded the diazonium salt, which was then reacted with ferrocene in situ to yield the meta-substituted ferrocenyl ethyl benzoate 1.…”

mentioning

confidence: 99%

mentioning

confidence: 99%

See 4 more Smart Citations

The synthesis and structural characterization of novel N-meta-ferrocenyl benzoyl amino acid esters

Savage

Neary

Malone

et al. 2005

Inorganic Chemistry Communications

Self Cite

View full text Add to dashboard Cite

A series of N-meta-ferrocenyl benzoyl amino acid esters 3-10 have been prepared by coupling meta-ferrocenyl benzoic acid 2 to the amino acid esters using the conventional 1,3-dicyclohexylcarbodiimide (DCC), 1-hydroxybenzotriazole (HOBt) protocol. The amino acids employed in the synthesis were glycine, L-alanine, L-leucine, L-phenylalanine, b-alanine, 4-aminobutyric acid, 2-aminobutyric acid and 2-aminoisobutyric acid. The compounds were fully characterized by a range of NMR spectroscopic techniques and mass spectrometry (MALDI-MS, ESI-MS).The organometallic compound ferrocene is a promising candidate for incorporation in novel materials due to its stability, spectroscopic properties, electrochemical properties and ease of use. As a direct consequence of these factors, research in the area of ferrocenyl derivatives has seen a dramatic increase in attention over the past decade, primarily for the ultimate goals of achieving novel sensor compounds, peptide mimetic models and unnatural drugs [1][2][3][4][5][6][7][8][9][10]. The incorporation of a ferrocene group onto proteins has shown the mediation of electron transfer between electrodes and the protein redox site [3,5]. The synthesis and structural characterization of novel N-ferrocenoyl and N-ferrocenyl amino acid and peptide derivatives has been reported [11][12][13][14][15][16][17][18][19][20][21][22][23][24][25][26][27][28]. The aim of this research is to incorporate three key moieties in the synthesis of unusual biological materials, namely (i) an electroactive core, (ii) a conjugated linker that can act as a chromophore and (iii) an amino acid derivative that can interact with other molecules via hydrogen bonding. In this communication, we report the synthesis and structural characterization of a series of novel Nmeta-ferrocenyl benzoyl amino acid ester derivatives. We recently reported the synthesis and structural characterization of a series of N-para-ferrocenyl benzoyl amino acid ester derivatives [28] and the N-ortho-ferrocenyl benzoyl amino acid derivatives will be reported in due course.The meta-ferrocenyl benzoic acid 2 was prepared using conventional diazonium salt chemistry. Treatment of ethyl-3-aminobenzoate with sodium nitrite in the presence of hydrochloric acid yielded the diazonium salt, which was then reacted with ferrocene in situ to yield the meta-substituted ferrocenyl ethyl benzoate 1. The ester group was cleanly cleaved by treatment with 10% sodium hydroxide to yield meta-ferrocenyl benzoic acid 2. The 1 H NMR spectrum showed signals for the aromatic ring protons at d 8.03 (s), d 7.8 (d), d 7.77 (d) and d 7.43 (t), integrating for one proton each, characteristic of a meta-disubstituted aromatic ring. The 1387-7003/$ -see front matter Ó (P.T.M. Kenny). www.elsevier.com/locate/inoche Inorganic Chemistry Communications 8 (2005) 429-432carboxylic acid proton was present at d 13.2. The ferrocenyl ortho and meta protons on the (g 5 -C 5 H 4 ) ring were observed at d 4.84 and d 4.39, respectively, and an intense singlet was present at d 4.03 for ...

show abstract

contrasting

confidence: 73%

mentioning

confidence: 97%

mentioning

confidence: 99%

mentioning

confidence: 99%

mentioning

confidence: 99%

See 3 more Smart Citations

The synthesis and structural characterization of novel N-meta-ferrocenyl benzoyl amino acid esters

Savage

Neary

Malone

et al. 2005

Inorganic Chemistry Communications

Self Cite

View full text Add to dashboard Cite

show abstract

Recent advances in the synthesis, biological activities and various applications of ferrocene derivatives

Larik

Saeed

Fattah

et al. 2016

Applied Organom Chemis

129

View full text Add to dashboard Cite

Ferrocene derivatives constitute an important class of organometallic compounds with not only an extensive range of biological activities but also diverse industrial as well as material science applications. These stimulating features of ferrocene derivatives spurred us to review the recent advances in synthesis methods and biological and other applications reported in the latest literature. An effort has been made to summarize the recent developments in synthetic methods providing access to ferrocene scaffolds and the useful medicinal and material applications, including agricultural, catalytic, polymer, conducting, redox mediating, ferrocenyl stationary phase, rocket propellant and ion sensing applications. Ferrocene‐based bulky metallocenes are also discussed.

show abstract

Heteroleptic Dirhodium(II) Complexes with Redox‐Active Ferrocenyl Ligands: Synthesis, Electrochemical Properties, and Redox‐Responsive Chemoselectivity in Carbene C−H Insertion

et al. 2022

View full text Add to dashboard Cite

A series of original heteroleptic dirhodium(II) complexes (4 a–j) of formula [Rh2(OAc)3(L)], where L is a redox‐active ferrocenecarboxylate ligand, has been prepared. These dirhodium(II) complexes have been characterised by NMR, mass spectrometry and cyclic voltammetry. All complexes show a quasi‐reversible redox behaviour for the ferrocenyl unit. The latter can be selectively oxidised by [N(4‐C6H4Br)3]+BF4−. Four selected heteroleptic complexes 4 a, 4 b, 4 f and 4 i, have been evaluated as catalysts for the intramolecular decomposition of a diazo compound 5. The ratio between the aromatic substitution product 6 and the aliphatic C−H insertion product 7 increases (up to 19 % increase) when using the in situ generated oxidised form of the dirhodium(II) complexes (4 a+BF4− to 4 i+BF4−). This shows that the oxidation of the ferrocenecarboxylate ligand has an effect on the chemoselectivity of the dirhodium‐catalysed diazo decomposition, and thus that the electronic properties of a complex can be tuned without exchanging ligands.

show abstract

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

Cited by 28 publications

References 29 publications

The synthesis and structural characterization of novel N-meta-ferrocenyl benzoyl amino acid esters

The synthesis and structural characterization of novel N-meta-ferrocenyl benzoyl amino acid esters

Recent advances in the synthesis, biological activities and various applications of ferrocene derivatives

Heteroleptic Dirhodium(II) Complexes with Redox‐Active Ferrocenyl Ligands: Synthesis, Electrochemical Properties, and Redox‐Responsive Chemoselectivity in Carbene C−H Insertion

Contact Info

Product

Resources

About