230951-82-3Relevant academic research and scientific papers
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
Sheehy, Michael J.,Gallagher, John F.,Yamashita, Mashita,Ida, Yoshiteru,White-Colangelo, Jennifer,Johnson, Jeremi,Orlando, Ron,Kenny, Peter T.M.
, p. 1511 - 1520 (2004)
The N-ferrocenoyl amino acid ester derivatives FcCOR {Fc=(η5-C5H5) Fe(η5-C5H4)} where R=Gly(OMe) 1, Gly(OEt) 2, Gly(OBn) 3, l-Ala(OMe) 4, l-Ala(OEt) 5, l-Leu(OMe) 6, l-Leu(OEt) 7, l-Leu(OBn) 8, l-Phe(OMe) 9 and l-Phe(OEt) 10, were prepared by coupling ferrocene carboxylic acid with the appropriate amino acid ester starting materials using the 1,3-dicyclohexylcarbodiimide (DCC), 1-hydroxybenzotriazole (HOBt) protocol and these have been characterised by spectroscopic techniques. The electrochemical anion sensing behaviour of compounds 1-10 with several anions using a platinum microdisk working electrode is described, together with 1H NMR anion complexation studies. The X-ray single crystal structure of N-ferrocenoyl-l-alanine methyl ester 4 has been determined and contains two molecules which differ slightly in conformation in the asymmetric unit of space group P21 (No. 4); principal dimensions are amide N(H)C=O 1.224(6) and 1.231(6) A?, ester C=O 1.220(10) and 1.190(7) A?, with N-H?O=C(amide) as the primary intermolecular hydrogen bond, N?O 2.992(6) and 2.971(6) A? and with graph set C(4).
