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Article type: Research Article
Authors: Ioannou, Panayiotis V. | Tsivgoulis, Gerasimos M.
Affiliations: Department of Chemistry, University of Patras, Patras, Greece
Note: [] Corresponding authors: Panayiotis V. Ioannou and Gerasimos M. Tsivgoulis, Department of Chemistry, University of Patras, Patras, Greece. Fax: +30 2610 997 118; E-mails: ioannou@chemistry.upatras.gr (Panayiotis V. Ioannou); tsivgoulis@chemistry.upatras.gr (Gerasimos M. Tsivgoulis).
Note: [] Corresponding authors: Panayiotis V. Ioannou and Gerasimos M. Tsivgoulis, Department of Chemistry, University of Patras, Patras, Greece. Fax: +30 2610 997 118; E-mails: ioannou@chemistry.upatras.gr (Panayiotis V. Ioannou); tsivgoulis@chemistry.upatras.gr (Gerasimos M. Tsivgoulis).
Abstract: Arsenic trioxide, but not bismuth trioxide, reacted with the oral anti-hypertensive drug captopril giving the anhydrous (and in one case the dihydrated) tris(captoprilato)arsenic in good yields. Bismuth(III) nitrate pentahydrate reacted with 1, 2, 3 equivalents of captopril giving solutions containing the corresponding thiolato complexes and nitric acid. Their 1H NMR spectra in CD3OD showed that both major and minor captoprilato conformers existed and the more captoprilato ligands are coordinated to Bi(III) the more up field the CH2S protons resonate. Addition of a calculated amounts of NaOH to the solutions of Bi(III)/captopril 1:1 and 1:2 gave solids insoluble in methanol or DMSO, the structures of which could not be reliably established by IR. The IR spectra of the isolated tris(captoprilato)arsenic and bismuth showed two νC = O bands for the COOH groups implying a complex hydrogen bonding network. These two complexes have sufficient solubility in water to be studied for biochemical or biological activities.
Keywords: Captopril, As(III) trithiolates, Bi(III) thiolates, $^1$H NMR
DOI: 10.3233/MGC-130104
Journal: Main Group Chemistry, vol. 12, no. 3, pp. 221-233, 2013
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