M. Sheehy, J. Gallagher, M. Yamashita
May 1, 2004
Citations
0
Influential Citations
20
Citations
Journal
Journal of Organometallic Chemistry
Abstract
Abstract 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)CO 1.224(6) and 1.231(6) A, ester CO 1.220(10) and 1.190(7) A, with N–H⋯OC(amide) as the primary intermolecular hydrogen bond, N⋯O 2.992(6) and 2.971(6) A and with graph set C(4).