Syntheses,characterization of and studies on the electrochemical behaviour of ferrocenyl dithiophosphonates and 4-methoxyphenyl dithiophosphonates |
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Authors: | Ertuğrul Gazi Sağlam Sevcan Erden Özgür Tutsak Dilek Eskiköy Bayraktepe Zehra Yazan Durmuş Hakan Dal |
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Institution: | 1. Department of Chemistry, Bozok University, Yozgat, Turkeysaglameg@gmail.com;3. Department of Chemistry, Ankara University, Tando?an, Ankara, Turkey;4. Department of Chemistry, Bozok University, Yozgat, Turkey;5. Department of Chemistry, Anadolu University, Yeniba?lar, Eski?ehir, Turkey |
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Abstract: | Some 1,3-dithiadiphosphetane 2,4-disulfides (X2P2S4, X: Fc, FcLR; X: CH3O?C6H4?, LR) were allowed to react with alcohols to obtain dithiophosphonic acids (X(OR)PS2H). These were converted to the corresponding ammonium salts. The salts were of the structures Fc(OR)PS2]?NH4]+, R: 3-methyl-1-butyl- for I; 1-phenyl-1-propyl- for II; 3-pentyl- for III; 3-phenyl-1-propyl- for IV and CH3O?C6H4(OR)PS2]?NH4]+, R: 3-methyl-1-butyl- for V and 1-phenyl-1-propyl- for VI. To the best of our knowledge, all the compounds except V were prepared for the first time.The compounds synthesized were characterized by elemental analysis, NMR (1H, 13C, 31P), MS, FTIR, and Raman spectroscopies. Electrochemical behaviors of I–VI at disposable pencil graphite electrode (PGE) were investigated by using cyclic voltammetry (CV) and square-wave voltammetry (SWV). Adsorption and diffusion patterns of all the compounds on the PGE were also studied.Two electroactive groups were identified in the compounds I–IV and only one in V and VI. The ferrocenyl groups of I-IV were oxidized at around 0.4 V. The same compounds display a second, more intense CV band at 0.8 V. The corresponding band for the compounds V–VI appears at around 0.6 V with a much weaker intensity. It is suggested that the ferrocenyl group introduced into the structures stabilizes the radical species formed as the product of the oxidation of the dithiophosphonato group. |
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Keywords: | Ferrocenyl Lawesson reagent Lawesson reagent ferrocenyl-dithiophosphonate thio-phosphorus compounds cyclic voltammetry |
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