Intramolecular hydrogen-bond participation in phosphonylammonium salt formation.
[reaction: see text] A series of phosphonochloridates and phosphonyl dichlorides were prepared, and their reactivity with triethylamine has been investigated using (31)P NMR spectroscopy. Taken together these studies provide evidence that an intramolecular hydrogen-bond is required for phosphonylammonium salt formation to render the phosphorus more electron-deficient.
Smith
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Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104, USA. smithab@sas.upenn.edu
Ducry
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Corbett
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Hirschmann
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D005021:Ethylamines / Q000737:chemistry; D006860:Hydrogen Bonding; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D063065:Organophosphonates / Q000138:chemical synthesis* / Q000737:chemistry; D000644:Quaternary Ammonium Compounds / Q000138:chemical synthesis* / Q000737:chemistry
D005021:Ethylamines; D007202:Indicators and Reagents; D063065:Organophosphonates; D000644:Quaternary Ammonium Compounds; C016162:triethylamine