Syntheses, spectroscopic study and crystal structures of some new N-benzoylphosphoric triamides

Gholivand, Khodayar; Shariatinia‬, Zahra

doi:10.1007/s11224-006-9132-z

Cited by 18 publications

(10 citation statements)

References 26 publications

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“…Similar results were obtained for the nitrogen atoms of structure 2b that confirm the sp 2 hybridization for the N atoms, although due to the repulsion and steric interactions, some angles are greater, and others are smaller than 120°. This observation suggests the existence of partial multiple bond character between phosphorus and nitrogen atoms that has always been confirmed by the crystallographic data of our previously reported similar compounds [29][30][31][32][33][34].…”

Section: X-ray Crystallographysupporting

confidence: 85%

Polymorphism for a novel phosphoramidate; NMR and X-ray crystallography

et al. 2010

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New phosphoramidates with formula 3-NC 5 H 4 C(O)NHP(O)XY (X=Y=Cl (1), X=Y=NH-C(CH 3 ) 3 (2a,2b), X=Y=N(C 4 H 9 ) 2 (3), X=Cl, Y=N(C 2 H 5 ) 2 (4) were synthesized and characterized by IR, 1 H-, 13 C-, 31 P-NMR spectroscopy and CHN elemental analysis. Surprisingly, the reaction of compound 2a with LaCl 3 , 7H 2 O in 3:1 M ratio leads to a polymorph of this compound (2b). NMR spectra indicate that 2 J(PNH amide ) in 2b (7.0 Hz) is very much greater than in 2a (4.1 Hz), while d( 31 P) values are identical for both of them. In IR spectra, t(P=O) is weaker but t(C=O) is stronger in 2a than in 2b. The structures of 2a, 2b were determined by X-ray crystallography. These compounds form centrosymmetric dimers via two intermolecular P=O……H-N hydrogen bonds. Strong intermolecular N-H…N, N-H…O and weak C-H…O hydrogen bonds lead to a three-dimensional polymeric cluster in the 2a while intermolecular strong N-H……N and weak C-H……O hydrogen bonds form a two-dimensional polymeric chain in 2b.

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Section: X-ray Crystallographysupporting

confidence: 85%

Polymorphism for a novel phosphoramidate; NMR and X-ray crystallography

et al. 2010

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“…Some researchers have employed the anionic form [P(O)NC(O)] -to obtain compounds with a non-anti orientation [8] and better donority properties [9]. Despite the numerous structures reported in this series [10][11][12][13][14][15][16][17][18][19], there are a few neutral structures with synclinal orientation [2,5,[13][14][15][16][17]19]. Here, we study on two new compounds with different orientations of C=O versus P=O.…”

Section: Introductionmentioning

confidence: 99%

Different orientations of C=O versus P=O in P(O)NHC(O) skeleton: the first study on an aliphatic diazaphosphorinane with a gauche orientation

et al. 2010

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Different orientations of P(O) versus C(O) in P(O)NHC(O) skeleton have been discussed in two new phosphorus(V)-nitrogen compounds with formula XP(O)Y and XP(O)Z 2 where X = NHC(O)C 6 H 4 (4-F) and Y = NHCH 2 C(CH 3 ) 2 CH 2 NH (1), Z = NHC 6 H 4 (4-CH 3 ) (2). Compound 1 is the first example of an aliphatic diazaphosphorinane with a gauche orientation which has been studied by X-ray crystallography; the P=O bond is in the equatorial position of the ring. Both compounds show n J(F,C) and m J(F,H) coupling constants (n = 1, 2, 3 and 4; m = 3 and 4) and 3 J(P,C) [ 2 J(P,C). Quantum chemical calculations were performed with HF and Density Functional Theory (DFT) methods using 6-31?G(d,p) basis set. A tentative assignment of the observed vibrational bands for these molecules is discussed. Compound 1 shows a deshielded C atom of the carbonyl moiety (in 13 C NMR spectrum) relative to that of 2, which is supported by IR spectroscopy in which the considerably lower C=O frequency is observed for 1. Comparing the X-ray crystallography and IR spectra of 1 and 2 shows that the acyclic compound 2, containing P=O and C=O bonds in an anti position, are involving in a stronger N-HÁÁÁO=P hydrogen bond in crystal network. This leads to a weaker P=O and N C(O)NHP(O) -H bonds and stronger NÁÁÁO interaction. The N amide -H is involved in an intramolecular N-HÁÁÁO hydrogen bond.

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“…This coupling was observed neither for compounds 11-19 nor for our previously reported phosphoric triamides. 24,25,[28][29][30][31][43][44][45] Typically, 4 J (H, H) coupling constants for the phenyl ring are in the range of 1-3 Hz and particular values seem to depend as much on the pattern of substitution as the nature of the substituent. 46 The 1 H NMR spectrum of compound 3 exhibited 3 J (H, H) cis = 10⋅3 Hz and 3 J (H, H) trans = 17⋅2 Hz for the coupling of terminal CH 2 protons of -CH=CH 2 with CH proton.…”

Section: Spectroscopic Studymentioning

confidence: 99%

“…The structures of several phosphoramidates have already been determined by X-ray crystallography. [20][21][22][23][24][25][26][27][28][29][30][31] N-benzoylphosphoric triamides are one such significant category of phosphoramidates derivatives. In fact, the existence of -C(O)NHP(O)-skeleton as peptide group in these molecules cause them biologically active urease inhibitors.…”

Section: Introductionmentioning

confidence: 99%

N-2,4-dichlorobenzoyl phosphoric triamides: Synthesis, spectroscopic and X-ray crystallography studies

2010

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New phosphoric triamides 1-9 were synthesized by the reaction of N-2,4-dichlorobenzoyl phosphoramidic dichloride with various cyclic aliphatic amines and the products were characterized by 1 H, 13 C, 31 P NMR, IR spectroscopy and elemental analysis. Surprisingly, the 1 H NMR spectrum of 2 indicated long range 6 J (P, H) coupling constant = 1⋅3, 1⋅4 Hz and those of molecules 3, 4, 6-8 display longrange 4 J (H, H) coupling constants (1⋅8-1⋅9 Hz) for the coupling of aromatic protons in 2,4-dichlorophenyl rings. 1 H NMR spectra indicated 3 J (PNCH) for enantiotopic and diastereotopic benzylic CH 2 protons in compounds 7 and 8. The spectroscopic data of newly synthesized compounds were compared with those related N-benzoyl derivatives. The structures of compounds 5, 8 and 10 (2,4-Cl 2 -2 ) have been determined by X-ray crystallography. The structures form centrosymmetric dimers through intermolecular strong -P=O…H-N-hydrogen bonds. The dimers connect to each other via rather strong and weak C-H…O plus weak C-H…Cl H-bonds to produce a 1-D network for 5 while 3-D polymeric chains for 8 and 10.

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Syntheses, spectroscopic study and crystal structures of some new N-benzoylphosphoric triamides

Cited by 18 publications

References 26 publications

Polymorphism for a novel phosphoramidate; NMR and X-ray crystallography

Polymorphism for a novel phosphoramidate; NMR and X-ray crystallography

Different orientations of C=O versus P=O in P(O)NHC(O) skeleton: the first study on an aliphatic diazaphosphorinane with a gauche orientation

N-2,4-dichlorobenzoyl phosphoric triamides: Synthesis, spectroscopic and X-ray crystallography studies

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