Exploring the Structural Chemistry of Pyrophosphoramides: <i>N</i>,<i>N</i>′,<i>N</i>″,<i>N</i>‴-Tetraisopropylpyrophosphoramide

<i>N</i>,<i>N</i>′,<i>N</i>″,<i>N</i>‴-Tetraisopropylpyrophosphoramide <b>1</b> is a pyrophosphoramide with documented butyrylcholinesterase inhibition, a property shared with the more widely studied octamethylphosphoramide (Schradan). Unli...

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Bibliographic Details
Main Authors: Duncan Micallef, Liana Vella-Zarb, Ulrich Baisch
Format: Article
Language:English
Published: MDPI AG 2021-01-01
Series:Chemistry
Subjects:
Online Access:https://www.mdpi.com/2624-8549/3/1/13
Description
Summary:<i>N</i>,<i>N</i>′,<i>N</i>″,<i>N</i>‴-Tetraisopropylpyrophosphoramide <b>1</b> is a pyrophosphoramide with documented butyrylcholinesterase inhibition, a property shared with the more widely studied octamethylphosphoramide (Schradan). Unlike Schradan, <b>1</b> is a solid at room temperature making it one of a few known pyrophosphoramide solids. The crystal structure of <b>1</b> 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 (<sup>1</sup>H) and Phosphorus 31 (<sup>31</sup>P) Nuclear Magnetic Resonance (NMR) spectroscopy, infrared (IR) spectroscopy, mass spectrometry (MS) were carried out to complete the analysis of the compound.
ISSN:2624-8549