Syntheses and Spectroscopic Studies of Some New Diazaphospholes and Diazaphosphorinanes. Crystal Structure of 4

Gholivand, Khodayar; Shariatinia‬, Zahra; Pourayoubi, Mehrdad; Farshadian, Sedigheh

doi:10.1515/znb-2005-1001

Cited by 18 publications

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“…Compound C 6 H 5 C(O)NHP(O)[NH-C(CH 3 ) 3 ] 2 showed two conformers in solution NMR spectra and solid state [14]. Moreover, compounds C 6 H 5 C(O)NHP(O)X 2 , X = NC 3 H 6 [15], NC 4 H 8 [16] 4-CH 3 -C 6 H 4 OP(O)(NH-CH (CH 3 )(CH 2 C 6 H 5 ) [17] and C 6 H 5 C(O)NHP(O)(NC 5 H 10 ) 2 [18] 4-F-C 6 H 4 C(O)NH P(O)(NC 5 H 10 ) 2 [19] exhibited two and four conformers, respectively, only in their crystalline states. The synthesis and structure of compound {(1R, 2S)-N-i Pr-ephedrine}P(S)NH[(Si(CH 3 ) 3 ], which is an oxazaphosphole molecule with three independent molecules in the crystalline lattice, was reported [20].…”

Section: Introductionmentioning

confidence: 98%

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

Gholivand

Shariatinia‬

2007

Struct Chem

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The reaction of N-benzoylphosphoramidic dichloride with amines afforded some new N-benzoylphosphoric triamides with formula C 6 H 5 C (4) and N(CH 3 ) (C 6 H 11 ) (5) that were characterized by 1 H, 13 C, 31 P NMR, IR spectroscopy and elemental analysis. The structures have been determined for compounds 4 and 5 by X-ray crystallography. These compounds contain one amidic hydrogen atom and form centrosymmetric dimmers via intermolecular -P=O · · · H-N-hydrogen bonds besides weak C-H · · · O hydrogen bonds that lead to three-dimensional polymeric clusters in the crystalline lattice.

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Section: Introductionmentioning

confidence: 98%

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

Gholivand

Shariatinia‬

2007

Struct Chem

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“…Nowadays, modification of cyclophosphamide (an oxazaphosphorinane compound) have led to the design and synthesis of numerous cyclic analogous compounds [4][5][6][7][8] to find an antitumor agent that has less side effects than drugs now present. The chemistry of 1,3,2-oxaza- [9,10] and dioxa-phosphorinanes [11,12], as well as the synthesis [13,14], stereochemistry [15], coordination chemistry [16,17] and, X-ray crystal structures [4,18] of 1,3,2-diazaphosphorinanes have frequently been studied. According to the stereochemical surveys, 1,3,2-diazaphosphorinanes prefer chair or flattened chair conformations, in contrast to 1,3,2-oxazaphosphorinanes which have diverse conformations [19].…”

Section: Introductionmentioning

confidence: 99%

The first naphthodiazaphosphorinane in the solid phase; syntheses, spectroscopic studies and X-ray crystallography of some new 1,3,2-diheterophosphorus compounds

et al. 2009

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New heterocyclic compounds of diazaphosphorinanes, diazaphospholes, and oxazaphospholes were synthesized and characterized by 1 H, 13 C, 31 P, NMR, IR spectroscopy, and CHN elemental analysis. The 3D structure of compound (5) was determined by X-ray crystallography. Since benzo-or naphthodiazaphospholes/diazaphosphorinanes containing aromatic rings are usually unstable in the solution state, their single crystal structures are rarely reported and, to the best of our knowledge, this structure is the first occasion of naphthodiazaphosphorinanes obtained here. It is noticeable that the P=O and C=O bonds are closer to syn than anti configuration and the P=O bond is placed in a pseudoequatorial position. This structure produced a 3D polymeric chain via strong hydrogen bonds and electrostatic short contacts. Due to the ring strain of five-membered rings, for all diazaphospholes great 2 J(PNH endocyclic ) coupling constants (about 18.0 Hz), as well as high 2,3 J(P,C) coupling constants for the aromatic carbon atoms connected to the five-membered ring (about 14.5, 13.5 Hz, respectively) were measured. Replacement of one NH group in a diazaphosphole ring by an oxygen atom caused exceedingly decreased ring strain and hence highly diminished 2 J(PNH endocyclic ) coupling constant.Furthermore, 31 P NMR spectra of oxazaphospholes, like the spectra of diazaphosphorinanes, indicated highly shielded phosphorus atoms relative to those of their diazaphospholes analogs.

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“…Hutchins et al studied the conformational analysis of 1,3-diazaphosphorinanes as well as their 1 H-and 31 P NMR spectroscopy [3]. Synthesis, conformational properties, and crystal structures [4,5] of several diazaphosphorinanes were reported [6][7][8][9]. Investigations on doubly connected phosphorus cations were made in some 1,3-diazaphosphorinanes [10].…”

Section: Introductionmentioning

confidence: 99%

Phosphorus heterocycles: synthesis, spectroscopic study and X-ray crystallography of some new diazaphosphorinanes

et al. 2007

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New diazaphosphorinanes with formula C 6 H 5 OP(O)[NHCH 2 C(CH 3 ) 2 CH 2 NH] (1), RP(O)[NH(CH 2 ) 3 NH], R=C 6 H 5 O (2), 4-CH 3 -C 6 H 4 NH (3), 4-NO 2 -C 6 H 4 NH (4), RP(O)[NHC 10 H 6 NH],R=Cl (5), 4-CH 3 -C 6 H 4 O (6), and C 6 H 5 NH (7) were synthesized and characterized by 1 H, 13 C, 31 P NMR and IR spectroscopy and elemental analysis. The crystal structures of compounds 1 and 4-CH 3 -C 6 H 4 OP(O)[NH(CH 2 ) 3 NH] (8) were determined using X-ray crystallography. In these structures, the P=O bond is placed in an equatorial position and the aliphatic six-membered rings show chair conformations. These compounds form two-dimensional polymeric chains via intermolecular P=O…H-N hydrogen bonds. 1 H NMR spectrum of compound 1 shows a ddd splitting pattern for the coupling of H equatorial proton with phosphorus atom, H axial atom, and NH proton with a highvalue 3 J(PNCH) coupling constant = 26.1 Hz. But, H axial indicates a dd splitting pattern because of the coupling with H equatorial and NH protons. 13 C NMR spectra of compounds 5-7, indicated high values for 3 J(P,C) aromatic = 11.9, 11.3 and 10.2 Hz due to the coupling of the aromatic carbon atom of naphthalene moiety with the phosphorus atom. 31 P NMR spectra indicate that the d( 31 P) of compounds 1-4 and 8 containing NH groups connected to the aliphatic carbon atoms appear downfield relative to those of compounds 5-7 that containing NH groups connected to the aromatic naphthalene group.Graphical abstract 4-CH 3 -C 6 H 4 OP(O)[NH(CH 2 ) 3 NH]

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Syntheses and Spectroscopic Studies of Some New Diazaphospholes and Diazaphosphorinanes. Crystal Structure of 4

Cited by 18 publications

References 0 publications

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

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

The first naphthodiazaphosphorinane in the solid phase; syntheses, spectroscopic studies and X-ray crystallography of some new 1,3,2-diheterophosphorus compounds

Phosphorus heterocycles: synthesis, spectroscopic study and X-ray crystallography of some new diazaphosphorinanes

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