کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
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1340470 | 979737 | 2008 | 11 صفحه PDF | دانلود رایگان |

Twenty new carbacylamidophosphates R′2P(O)NHC(O)R, where R = acetyl and benzoyl derivatives, R′ = 3, 5, 6 and 7 membered ring amines, were synthesized and characterized by IR, 1H, 13C and 31P NMR spectroscopy, and elemental analysis. The crystal structures of CCl3C(O)NHP(O)[N(C5H10)]2 (1d), CHCl2C(O)NHP(O)[N(C5H10)]2 (2d), Cl–C6H4C(O)NHP(O)[NH(C5H9)]2 (5b) and Cl–C6H4C(O)NHP(O)[N(C4H8)O]2 (5e) have been determined. All four compounds indicate the formation of intermolecular –PO…H–N– hydrogen bonds which give dimeric aggregates. They were centrosymmetric in 5b and 5e. Also, the mass spectra of these compounds, in addition to our previously synthesized 29 carbacylamidophosphates, were recorded and the observed fragmentation behaviors were studied. The main pathways of fragmentation of N-acetyl and N-benzoyl phosphoric amide derivatives indicated that the molecular ions involve mainly a radical cationic center at the carboxyl oxygen. All the N-benzoyl and N-acetyl phosphoramidates rearranged to the O-phosphorylated benz- or acetamides, and those readily lost the (R′)2PO2 radicals and yielded N-protonated nitrilium ions R–CNH+ and . The greater intensities for the ions in the N-benzoyl derivatives relative to R–CNH+ for the N-acetyl derivatives may due to differences in the PO, CO, P–Namide and C–Namide bond lengths and their different specific properties in the parent molecules.
New carbacylamidophosphates, R′2P(O)NHC(O)R with N-benzoyl and N-acetyl derivatives were synthesized and their crystal structures and mass spectra were determined. The mass spectra showed that the greater intensities for ions for N-benzoyl derivatives relative to R–CNH+ ions for N-acetyl derivatives may due to different PO, CO, P–Namide and C–Namide bond lengths.Figure optionsDownload as PowerPoint slideFigure optionsDownload as PowerPoint slide
Journal: Polyhedron - Volume 27, Issue 6, 25 April 2008, Pages 1639–1649