X-ray structures of two phosphazo analogues of β-diketones: N,N′-diphenyl-N″-trichloracetyl- phosphorictriamide and N,N′-tetraethyl-N″-benzoyl-phosphorictriamide have been determined. The results obtained in this study and the data reported earlier allow to discuss the impact of various substitutents on the phosphoricamido C(O)N(H)P(O) moiety.
Carbacylamidophosphates, IR Data, X-Ray Data Dimorpholido-N-trichloroacetylphosphorylamide: CCl3C(0 )NHP(0 )[N(CH2CH2)2 0 ] 2 [HL] and its sodium [NaL] and morpholine [HN(CH2CH2 ) 2 0 HL] salts were synthesized for the first time. The compounds were studied by IR spectroscopy and assignments of the characteristic IR bands have been made. The structure of [HL] was determined by X-ray diffraction. Crystals are monoclinic, a = 11.412(2) A, b = 16.056(3) A, c = 9.622(2) Ä, ß = 108.55(3)°, space group P2i/c; Z = 4. The refinement of the structure converged at R = 0.066. The molecules are connected into centrosymmetric dimers via hydrogen bonds formed by the phosphorylic oxygen atoms and hydrogen atoms of amide groups.
IntroductionCarbacylamidophosphates of the general formula R 'C (0 )N H P (0 )(R 2)2 are interesting as potential new ligands for metal ions [1 -4]. On the other hand, many of these compounds show interesting biological properties, including anticancer activ ity [5,6]. The X-ray structures of three carbacy lamidophosphates: CCl3C (0)N H P (0)(0M e)2 (I), CCl3C (0)N H P(0)(N E t2)2 (II), and CCl3C (0)N H P(0)(N H Ph)2 (III) were studied ear lier [7 -9 ]. The results have shown that in the molec ular core unit, -C (0)N (H )P(0)=, the C = 0 and P = 0 oxygen atoms are in trans position to each other, and that the C -C (0)N -unit is virtually planar.This work reports the synthesis, the structure de termination and the properties of dimorpholido-Ntrichloroacetylphosphorylamide and its sodium and morpholine salts. Experimental The synthesis of the dimorpholido-N-trichloroacetylphosphorylamide was carried out according to the scheme: CC13C(0)NHP(0)C12 + 5HN(CH2CH2)20 -*• CC13C(0)NHP(0)[N(CH2CH2)20]2HN(CH2CH2)20 + 2 HN(CH2CH2)20 HC1 * Reprint requests to Dr. V. Amirkhanov. The dichloride of trichloroacetylamidophosphoric acid was obtained by the method described earlier [1 0 ].The solution of morpholine [35 g (0.4 mol)] in 100 ml of benzene was placed into a three-neck round-bottomed flask and cooled to 10°C. A solution of the dichloride [23 g (0.083 mol)] of trichloroacetylamidophosphoric acid in 400 ml of a toluene-dioxane mixture (10:1) was added slowly with stirring.(The temperature was not al lowed to rise above 10°C!). Stirring was continued for about 40 min. The resulting mixture, containing the HN(CH2CH2)2O HL (HL = dimorpholide-N-trichloroacetylphosphorylamide) and HN(CH2CH2) 2 0 HC1, was filtered from the precipitate and HN(CH2CH2 ) 2 0 HL was extracted by acetone. Then the extract was evaporated and the residue was dissolved in water. After the addition of HC1 to the aqueous solution the product precipitated as a white crystalline powder (80% yield).Single crystals for the structure investigations were obtained by recrystallization from methanol.The product, m.p. 205 °C with the decomposition, is soluble in methanol and acetone, less soluble in nonpolar aprotic solvents, and essentially insoluble in water.The sodium salt [NaL] was obtained from methanol solution with sodium methoxide. It is a white...
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