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Synthesis and Characterization of Novel Carbacylamidophosphate Derivatives: Crystal Structures of (p‐Cl‐C 6 H 4 )C(O)NHP(O)(NC 5 H 10 ) 2 and (p‐Br‐C 6 H 4 )C(O)NHP(O)(NC 5 H 10 ) 2
Author(s) -
Gholivand Khodayar,
Mojahed Fresia,
Alizadehgan Ahlam Madani,
Bijanzadeh Hamid Reza
Publication year - 2006
Publication title -
zeitschrift für anorganische und allgemeine chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.354
H-Index - 66
eISSN - 1521-3749
pISSN - 0044-2313
DOI - 10.1002/zaac.200600055
Subject(s) - cyclohexylamine , piperidine , crystal structure , chemistry , dimer , crystallography , molecule , stereochemistry , organic chemistry
Abstract Using phosphorus pentachloride as a substrate, carbacylamidophosphates of the general formula (p‐X‐C 6 H 4 ) C(O)NHP(O)(R) 2 ; (X=Cl and R=Cl, 2a ; X=Br and R=Cl, 3a ; X=Me and R=Cl, 4a ; X=Cl and R=piperidine, 2b ; X=Br and R=piperidine, 3b ; X=Me and R=piperidine, 4b ; X=H and R=cyclohexylamine, 1c ; X=Cl and R=cyclohexylamine, 2c ; X=Br and R=cyclohexylamine, 3c ; X=Me and R=cyclohexylamine, 4c ; X=H and R=p‐Me‐cyclohexylamine, was prepared and characterized by 1 H, 31 P and 13 C NMR and IR spectroscopy and elemental analysis. Different group attached on phosphorus nuclei affect on IR and NMR spectra. Three‐bond coupling constants between phosphorus and carbon nucleus, 3 J(P,C aliphatic ) in the 1b – 4b and 1c – 4c containing piperidine or cyclohexylamine groups, were greather than two‐bond coupling constants, 2 J(P,C aliphatic ). The structures of 2b and 3b were determined by single‐crystal X‐ray diffraction techniques. The both molecule crystals are composed of a centrosymmetric dimer via N‐H···O bonds. 3b exists as two independent molecules in crystal lattice.