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Phosphine appears to be mainly a redox toxin, causing cell damage by inducing oxidative stress and mitochondrial dysfunction. [35] Resistance in insects is caused by a mutation in a mitochondrial metabolic gene. [29] Phosphine can be absorbed into the body by inhalation. The main target organ of phosphine gas is the respiratory tract. [36]
Phosphines or phosphanes are phosphorus compounds derived from phosphine and have the general structure R 3 P. For the nitrogen analogues, please see Category:Inorganic amines . Wikimedia Commons has media related to Phosphines .
Phosphine (PH 3) and its organic derivatives (PR 3) are structural analogues of ammonia (NH 3), but the bond angles at phosphorus are closer to 90° for phosphine and its organic derivatives. Phosphine is an ill-smelling, toxic gas. Phosphorus has an oxidation number of −3 in phosphine. Phosphine is produced by hydrolysis of calcium phosphide ...
Organophosphines, like phosphine itself, are pyramidal molecules with approximate C 3v symmetry. The C–P–C bond angles are approximately 98.6°. [ 3 ] The C–P–C bond angles are consistent with the notion that phosphorus predominantly uses the 3p orbitals for forming bonds and that there is little sp hybridization of the phosphorus atom.
The first phosphorine to be isolated is 2,4,6-triphenylphosphorine. It was synthesized by Gottfried Märkl in 1966 by condensation of the corresponding pyrylium salt and phosphine or its equivalent ( P(CH 2 OH) 3 and P(SiMe 3) 3). [3] The (unsubstituted) parent phosphorine was reported by Arthur J. Ashe III in 1971.
Hypophosphorous acid was first prepared in 1816 by the French chemist Pierre Louis Dulong (1785–1838). [4]The acid is prepared industrially via a two step process: Firstly, elemental white phosphorus reacts with alkali and alkaline earth hydroxides to give an aqueous solution of hypophosphites:
Compounds related to phosphine oxides include phosphine imides (R 3 PNR') and related chalcogenides (R 3 PE, where E = S, Se, Te). These compounds are some of the most thermally stable organophosphorus compounds. In general, they are less basic than the corresponding phosphine oxides, which can adduce to thiophosphoryl halides: [7]: 73
Bis(2-cyanoethylphenyl)phosphine, which is of interest as a synthetic intermediate, can be made from phenylphosphine by base-catalyzed allylic addition to acrylonitrile. C 6 H 5 PH 2 + 2CH 2 =CHCN → C 6 H 5 P(CH 2 CH 2 CN) 2. Bis(2-cyanoethylphenyl)phosphine is a useful precursor to 1-phenyl-4-phosphorinanone by base-induced cyclization ...