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. 2016;191(3):405-410.
doi: 10.1080/10426507.2015.1091828. Epub 2016 Jan 14.

NEW METHOD FOR THE SYNTHESIS OF AMMONIUM SALTS OF O,O'-ALKYLENEDITHIOPHOSPHORIC ACID AND OCTATHIOTETRAPHOSPHETANE. CRYSTAL STRUCTURE FEATURES'S OF DIETHYLAMMONIUM SALT OF O,O'-PROPYLENEDITHIOPHOSPHORIC ACID

Elena K Badeeva  1 , Angelo Santomenna  2 , Aidar T Gubaidullin  1 , Liliya V Frolova  3 , Snezna Rogelj  2 , Elvira S Batyeva  1 , Oleg G Sinyashin  1
Affiliations

NEW METHOD FOR THE SYNTHESIS OF AMMONIUM SALTS OF O,O'-ALKYLENEDITHIOPHOSPHORIC ACID AND OCTATHIOTETRAPHOSPHETANE. CRYSTAL STRUCTURE FEATURES'S OF DIETHYLAMMONIUM SALT OF O,O'-PROPYLENEDITHIOPHOSPHORIC ACID

Elena K Badeeva et al. Phosphorus Sulfur Silicon Relat Elem. 2016.

Abstract

A new reaction of elemental phosphorus (P4) with elemental sulfur and 1,3-propylene glycol in the presence of different amines has been investigated. Ammonium salts of O,O'- alkylenedithiophosphoric acids have been observed as main products of the reaction. Octathiotetraphosphetane ammonium salts were formed as minor products. The reaction is characterized by a complete conversion of white phosphorus and is not accompanied by the release of hydrogen sulfide. The crystal structure features's of diethylammonium salt of O,O'-propylenedithiophosphoric acid were determined using single crystal X-ray diffraction. Piperidinium salt of octathiotetraphosphetane in DMSO and DMF solutions possess significant antifungal activity against Candida albicans.

Keywords: Elemental phosphorus; X-ray diffraction; ammonium salts of O,O′-alkylenedithiophosphoric acids and octathiotetraphosphetane.

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Figures

Figure 1
Figure 1
The geometry of cations and anions in the 1b crystals and the partial numbering scheme. Non-hydrogen atoms are represented by probability ellipsoids of thermal vibrations (p = 30%). Hydrogen atoms are not shown for clarity.
Figure 2
Figure 2
Two projections of the system of classic NH…O, NH…S hydrogen bonds (shown in thin dotted lines) between anions and cations in the crystal 1b. (a) View along 0c axis, showing one H-chain; (b) View along 0a axis, showing H-chains of all six independent anions-cations pairs.
Figure 3
Figure 3
System of NH…O, NH…S and C-H…O hydrogen bonds (thin dotted lines) in crystal 1b. Two independent anion-cation pairs are shown in the ball-stick model and the rest in the stick model. (a) View along 0a axis; (b) View along 0c axis.
Figure 4
Figure 4
Fragment of the anions and the cations crystal packing in 1b (Van der Waals representation). The view is along the axis 0a. The two selected H chains, mentioned in the discussion, are presented by green and purple colors.
See this image and copyright information in PMC

References

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    1. Sinyashin OG, Khodyrev Yu P, Batyeva ES, Badeeva EK, Platova EV, Kursheva LI. Phosphorus Sulfur Silicon. 2011;186:997–998.
    1. Khodyrev Yu P, Batyeva ES, Badeeva EK, Platova EV, Tiwari L, Sinyashin OG. Corrosion Sci. 2011;53:976–983.
    1. Batyeva ES, Badeeva EK, Platova EV, Gubaidullin AT, Porch N, Edwards L, Malik I, Frolova LV, Magedov IV, Rogelj S, Sinyashin OG. Heteroatom Chem. 2013;24:163–167.
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