Abstract
Abstract The synthesis of tetrakis(alkyl/arylamino)phosphonium compounds of type (RNH)4PX, where R = n-C3H7 (1), i-C3H7 (2), n-C4H9 (3), s-C4H9 (4), n-C5H11 (5), n-C6H13 (6), c-C6H11 (7), n-C7H15 (8), C6H5CH2 (9) and C6H5 (10), and where X = Cl, Br, I and ClO4, is described. These compounds have been characterized by elemental analysis, melting point and 1H and 31P NMR spectroscopy. Solubility characteristics in water and organic solvents are given for the chlorides, which have been found in general less soluble than the corresponding perchlorates. Metathesis reactions of the (RNH)4PCl compounds are shown to proceed with relative ease and have provided an adequate method for the conversion of the chlorides to bromides, iodides and perchlorates. Hydrolysis reactions for compounds 3, 9 and 10 have been studied and compared. Their relative stability toward base hydrolysis is demonstrated by the conditions used and the isolated intermediates identified, consistent with the postulated base hydrolysis scheme. NMR results are consistent with a structure for these compounds similar to the regular phosphonium salts, and represented as [(RNH)4P]+X−, where the amino groups are arranged around the phosphorus atom in a tetrahedral fashion. Finally, N-H stretching frequencies are presented for the series (n-C4H9NH)4PX, where X = Cl, Br, I, ClO4, and it is suggested on this basis that hydrogen bonding for the cases where X = Cl, Br, I plays an important role in the chemistry and structure of these compounds.
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