Abstract
N,N′,N″,N‴-Tetraisopropylpyrophosphoramide 1 is a pyrophosphoramide with documented butyrylcholinesterase inhibition, a property shared with the more widely studied octamethylphosphoramide (Schradan). Unlike Schradan, 1 is a solid at room temperature making it one of a few known pyrophosphoramide solids. The crystal structure of 1 was determined by single-crystal X-ray diffraction and compared with that of other previously described solid pyrophosphoramides. The pyrophosphoramide discussed in this study was synthesised by reacting iso-propyl amine with pyrophosphoryl tetrachloride under anhydrous conditions. A unique supramolecular motif was observed when compared with previously published pyrophosphoramide structures having two different intermolecular hydrogen bonding synthons. Furthermore, the potential of a wider variety of supramolecular structures in which similar pyrophosphoramides can crystallise was recognised. Proton (1H) and Phosphorus 31 (31P) Nuclear Magnetic Resonance (NMR) spectroscopy, infrared (IR) spectroscopy, mass spectrometry (MS) were carried out to complete the analysis of the compound.
Highlights
N,N,N,N -Tetraisopropylpyrophosphoramide 1 (O((iPrNH)2PO)2) is a commercially available pyrophosphoramide known to be a butyrylcholinesterase inhibitor [1,2]
The molecular structure of the compound is known, crystallographic support for this structure has not been published. Another pyrophosphoramide that has shown cholinesterase inhibition is octamethylpyrophosphoramide (O(Me2N)2PO)2), which is commonly known as Schradan
Gas chromatography Mass spectroscopy (GC mass spectrometry (MS)) data was collected using a Thermo DSQ II GC/MS spectrometer with samples being prepared by dissolution of the products in chloroform
Summary
N,N ,N ,N -Tetraisopropylpyrophosphoramide 1 (O((iPrNH)2PO)2) is a commercially available pyrophosphoramide known to be a butyrylcholinesterase inhibitor [1,2]. The molecular structure of the compound is known, crystallographic support for this structure has not been published Another pyrophosphoramide that has shown cholinesterase inhibition is octamethylpyrophosphoramide (O(Me2N)2PO)2), which is commonly known as Schradan. This compound, unlike 1, was used as an insecticide for sucking and chewing insects, which are agricultural pests but it has fallen out of use since the 1950’s [3,4]. In the mid-twentieth century, apart from its use as a pesticide, Schradan was studied for its chelation ability with numerous metal centres. Six other analogues of pyrophosphoramides were found in the literature, namely N,N ,N ,N -Tetrakis(2methylphenyl)- oxybis(phosphonic diamide) (O((2-MePh)NH)2PO)2), N,N ,N ,N -tetratert-butoxybis(phosphonic diamide) (O((tBuNH)2PO)2), N,N ,N ,N -tetrakis(4-methylphenyl)oxybis(phosphonic diamide) (O((4-MePh)NH)2PO)2), N,N ,N ,N -tetrakis(benzyl)-N,N , N ,N -tetrakis(methyl)oxybis-(phosphonicdiamide) (O((BzMeN)2PO)2), 2,2 -Oxybis(1,3bis(2,6-diisopropylphenyl)-1,3,2-diaza-phospholidine) 2,2 -dioxide (O((C2H4(2,5-iPrPhN)2) PO)2) and 2,2 -oxybis(1,3-bis- [(naphthalen-1-yl)methyl]octahydro-1H-1,3,2λ5-benzodiaza phosphol-2-one) monohydrate (O((1,2-Cy(NaphN)2)2PO)2·H2O) [10,11,12,13,14,15]
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