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Synthesis of phosphinic acids
Kruliš, Tomáš ; Kubíček, Vojtěch (advisor) ; Schulz, Jiří (referee)
Two types of phosphinic acids were prepared: N,N-bis(carboxymethyl)aminomethyl phosphinic acid and carboxyethylphosphinic acid. Afterwards they were used to synthesize bisphosphinic acids: 1-hydroxy-ethan-1,1-bis[N,N-bis(carboxymethyl)aminomethyl phosphinic] acid and 1-hydroxy-ethan-1,1-bis(carboxyethyl)phosphinic acid. All compounds were characterized by NMR and mass spectroscopy. N,N-bis(carboxymethyl)aminomethylphosphinic acid was synthesized by Mannich type reaction. Carboxyethylphosphinic acid was prepared by alkylation of bis(trimethylsilyloxy)phosphine. Both bisphosphinic acids were prepared by reaction of silylesters of phosphinic acids with acetylchloride. All compounds were prepared in moderate or good yields. Keywords: Organophosphorus synthesis, phosphinic acids, bisphosphinic acids
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Symmetrical aminophosphinates
Procházková, Soňa ; Kubíček, Vojtěch (advisor) ; Vojtíšek, Pavel (referee)
Title: Symmetrical aminophosphinates Author: Bc. Soňa Procházková Department of Inorganic Chemistry, Faculty of Science, Charles University Supervisor: RNDr. Vojtěch Kubíček, Ph.D. Supervisor's email address: kubicek@natur.cuni.cz ABSTRACT Two types of α-aminophosphinates were prepared and studied: phosphinate analogues of iminodiacetic acid − aminobis(methyl(hydroxymethyl)phosphinic acid) (IDPhm ) and aminobis(methyl(2-carboxyethyl)phosphinic acid) (IDPce ), and bis(aminomethyl- phosphinates) − (hydroxy(fenyl)methylen)bis(aminomethylphosphinic acid) (PheOHABPin) and (methylen)bis(aminomethylphosphinic acid) (ABPin). All prepared compounds were fully characterized (by NMR, MS, elemental analysis). One crystal structure was determined by X-ray singlecrystal analysis. The diphosphinates were synthesized by Mannich type reaction, whereas the bis(aminomethylphosphinates) were prepared by multistep synthesis including reactive silylesters. Compounds were prepared in moderate or good yields Acid-base and coordination properties of ligands were investigated and compared by potentiometric and NMR titrations. The values of protonation constants of aminogroups, which determine stability of complexes, showed surprising results. An extremely low basicity of nitrogen atom was found in diphosphinates. So, these compounds...
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Bis(phosphinates)
Křečková, Pavlína ; Kubíček, Vojtěch (advisor) ; Schulz, Jiří (referee)
Title: Bis(phosphinates) Autor: Pavlína Křečková Department: Department of Inorganic Chemistry, Faculty of Science Supervisor: RNDr. Vojtěch Kubíček, Ph.D. Supervisor's e-mail address: kubicek@natur.cuni.cz Abstract Four geminal bis(phosphinate) acids were prepared and characterized by TLC, NMR, MS, EA. The compounds were acquired in high yields (over 55 %). Stability of these compounds was tested in chosen aqueous buffers, which covered a wide range of pH. The experiments showed that the prepared compounds are not fully stable. Performed experiments have shown negligible sorption of synthesized bis(phosphic) acids to hydroxyapatite, which was used as a model of bone tissue. Keywords: geminal, bis(phosphinate), decomposition, sorption.
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Synthesis of alkylphosphinic acids
Procházková, Soňa ; Vojtíšek, Pavel (referee) ; Kubíček, Vojtěch (advisor)
The preparation of methylphosphinic acid and (3-terc-butoxy-3-oxopropyl)phosphinic acid using reaction between bis(trimethylsilyloxy)phosphine (BTSP) and iodomethane or tert-butyl acrylate was investigated. BTSP was generated in situ from ammonium phosphinate and hexamethyldisilazane. Simultaneously, the preparation of BTSP using N,O-bis(trimethylsilyl)acetamide was optimilized. The effect of conditions of the alkylation and addition reactions on the yield of monosubstituted and disubstituted phosphinic acids was examined. Furthemore, the preparation and properties of the BTSP-borane adduct and its possible employment in H-phosphinic acid syntheses were explored KEYWORDS: Organophosphorus synthesis, silylesters, borane adducts.
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