Affiliations: Department of Chemistry, Amirkabir University of Technology, Tehran, Iran | Department of Chemistry, Shahre-Rey Branch, Islamic Azad University, Tehran, Iran | Institute of Physics of the ASCR, v.v.i., Na Slovance Praha, Czech Republic
Note: [] Corresponding author: Zahra Shariatinia, Department of Chemistry, Amirkabir University of Technology, P.O. Box: 159163-4311, Tehran, Iran. E-mail: [email protected]
Abstract: New organophosphorus compounds with formula C6H5C(O)NHP(O)(2,4-OCH3-C6H3-NH)2 (1), CCl3C(O)NHP(O)(Cl)[N(C2H5)2] (2) and CF3C(O)NHP(O)(C6H5)2 (3) were synthesized and characterized by 1H, 13C, 31P NMR, IR spectroscopy and elemental analysis. The 31P{1H} NMR spectra indicate the most up field P atom in 2 exhibiting the most electron donation of the Cl atom which is due to its resonance effect. Among compounds 1–3, the ν(P=O) of 2 is the weakest while its ν(C=O) is the strongest one. This indicates that between two resonance forms (OH)C=N-P(O) (I) and O=CN-P(OH) (II), the interaction II is more preferred in 2. The structure of compound 4, P(O)(NC4H8N-C6H5)3, was determined by X-ray crystallography. In this molecule, a one dimensional polymeric chain is produced in the crystalline lattice by intermolecular weak C-H...O hydrogen bonds.
Keywords: Organophosphorus compounds, NMR, X-ray crystallography, hydrogen bond
