Diphenyl (<i>o</i>-tolylamido)phosphonate

Sabbaghi, Fahimeh; Pourayoubi, Mehrdad; Zargaran, Poorya

doi:10.1107/s1600536811013924

Cited by 4 publications

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“…Moreover, the IR frequencies were found to appear at 3162, 1178 and 756 cm −1 corresponding to N−H, P=O and P−N groups, respectively. The crystal structure has been previously published [55] …”

Section: Resultsmentioning

confidence: 99%

The Step‐Wise Synthesis of Oligomeric Phosphoramidates

et al. 2021

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In this study, the step‐wise synthesis to a series of higher phosphoramidates was explored, affording compounds containing N−P−N, symmetric and asymmetric P−N−P and P−N−P−N−P linkages. Salt elimination and lithiation strategies were employed to create the new P−N bonds. It was found that the steric bulk and electronic contribution of the substituents on the P(V) centers were important factors to the success of the reactions. The oligomeric phosphoramidates were characterized by multinuclear NMR and IR spectroscopies as well as ESI mass spectrometry. A selection of the synthesized P−N oligomers were evaluated for their antimicrobial activity against E.coli, S.aureus, C.albicans, and A.fumigatus at varying concentrations. The results suggest their potential use as environmentally friendly fire retardants as the minimal inhibitory concentration (MIC) value for all the compounds was found to be >128 μM, indicating that the compounds do not have any detectable antimicrobial activity.

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Section: Resultsmentioning

confidence: 99%

The Step‐Wise Synthesis of Oligomeric Phosphoramidates

et al. 2021

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Hirshfeld surface analysis of new phosphoramidates

Tarahhomi

Pourayoubi

Golen

et al. 2013

Acta Crystallogr B Struct Sci Cryst Eng Mater

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Hirshfeld surfaces and two-dimensional fingerprint plots are used to visualize and analyze intermolecular interactions in six new phosphoramidate structures, [2,6-F2-C6H3C(O)NH]P(O)[X]2 {X = N(C2H5)2 (1), [X]2 = NHCH2C(CH3)2CH2NH and with one CH3OH solvated molecule (2)}, [C6H5O]2P(O)Y [Y = NC4H8O (3), NHC6H4(3-Br) (4)] and [Z]2P(O)OP(O)[Z]2 [Z = N(CH3)(CH2C6H5) (5), NHC6H4(4-CH3) (6)]. Study of the short intermolecular contacts in structures (1)-(6) by Hirshfeld surfaces demonstrate that the O atom of P=O is a better H-atom acceptor than the O atom of C=O for (1) and (2), and also relative to the O atom of the C6H5O group for (3) and (4), and relative to the bridge O atom of the P(O)OP(O) segment for (5) and (6). The results confirm that the crystal packing is related to the kind of substituent linked to the P atom. Compounds (1), (2), (4) and (6), with characteristic N-H···O hydrogen bonds, show a pair of intense spikes (including the intermolecular H···O contacts) in the fingerprint plots, summarizing the major features of each structure in the related two-dimensional plot. For (3) and (5), without any N-H unit, the two short spikes are observed for (3) but are absent for (5). The upper d(e) and d(i) values (distances to the Hirshfeld surfaces for the nearest atoms outside and inside) in the fingerprint plots are more compact in (3) than in (4), and in (5) than in (6), reflecting the more efficient packing in (3) and (5). The tertiary N atoms of (3) and (5) do not take part in any intermolecular contacts involving H atoms. Moreover, structures (3)-(6) show greater contribution from C···H contacts relative to O···H contacts. Finally, Hirshfeld surfaces and fingerprint plots are employed for a comparison of the two independent molecules in the asymmetric unit of (1) and also, for a comparison of (6), in the orthorhombic crystal system, with the previously reported monoclinic polymorph (Pourayoubi, Fadaei et al., 2012).

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Conformational flexibility in amidophosphoesters: a CSD analysis completed with two new crystal structures of (C₆H₅O)₂P(O)X [X = NHC₇H₁₃ and N(CH₂C₆H₅)₂]

Alviri

Pourayoubi

Salam

et al. 2020

Acta Crystallogr C Struct Chem

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The crystal structures of diphenyl (cycloheptylamido)phosphate, C19H24NO3P or (C6H5O)2P(O)(NHC7H13), (I), and diphenyl (dibenzylamido)phosphate, C26H24NO3P or (C6H5O)2P(O)[N(CH2C6H5)2], (II), are reported. The NHC7H13 group in (I) provides two significant hydrogen-donor sites in N—H...O and C—H...O hydrogen bonds, needed for a one-dimensional hydrogen-bond pattern along [100] in the crystal, while (II), with a (C6H5CH2)2N moiety, lacks these hydrogen bonds, but its three-dimensional supramolecular structure is mediated by C—H...π interactions. The conformational behaviour of the phenyl rings in (I), (II) and analogous structures from the Cambridge Structural Database (CSD) were studied in terms of flexibility, volume of the other group attached to phosphorus and packing forces. From this study, synclinal (±sc), anticlinal (±ac) and antiperiplanar (±ap) conformations were found to occur. In the structure of (II), there is an intramolecular C ortho —H...O interaction that imposes a +sc conformation for the phenyl ring involved. For the structures from the CSD, the +sc and ±ap conformations appear to be mainly imposed by similar C ortho —H...O intramolecular interactions. The large contribution of the C...H/H...C contacts (32.3%) in the two-dimensional fingerprint plots of (II) is a result of the C—H...π interactions. The differential scanning calorimetry (DSC) analyses exhibit peak temperatures (T m) at 109 and 81 °C for (I) and (II), respectively, which agree with the strengths of the intermolecular contacts and the melting points.

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Diphenyl (o-tolylamido)phosphonate

Abstract: The asymmetric unit of the title compound, C19H18NO3P, contains two independent molecules in which the P atoms are found in slightly distorted tetrahedral environments. In the crystal, pairs of intermolecular N—H⋯O(P) hydrogen bonds form two independent centrosymmetric dimers.

Cited by 4 publications

References 4 publications

The Step‐Wise Synthesis of Oligomeric Phosphoramidates

The Step‐Wise Synthesis of Oligomeric Phosphoramidates

Hirshfeld surface analysis of new phosphoramidates

Conformational flexibility in amidophosphoesters: a CSD analysis completed with two new crystal structures of (C₆H₅O)₂P(O)X [X = NHC₇H₁₃ and N(CH₂C₆H₅)₂]

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Diphenyl (o-tolylamido)phosphonate

Abstract: The asymmetric unit of the title compound, C19H18NO3P, contains two independent mol­ecules in which the P atoms are found in slightly distorted tetrahedral environments. In the crystal, pairs of inter­molecular N—H⋯O(P) hydrogen bonds form two independent centrosymmetric dimers.

Cited by 4 publications

References 4 publications

The Step‐Wise Synthesis of Oligomeric Phosphoramidates

The Step‐Wise Synthesis of Oligomeric Phosphoramidates

Hirshfeld surface analysis of new phosphoramidates

Conformational flexibility in amidophosphoesters: a CSD analysis completed with two new crystal structures of (C6H5O)2P(O)X [X = NHC7H13 and N(CH2C6H5)2]

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Abstract: The asymmetric unit of the title compound, C19H18NO3P, contains two independent molecules in which the P atoms are found in slightly distorted tetrahedral environments. In the crystal, pairs of intermolecular N—H⋯O(P) hydrogen bonds form two independent centrosymmetric dimers.

Conformational flexibility in amidophosphoesters: a CSD analysis completed with two new crystal structures of (C₆H₅O)₂P(O)X [X = NHC₇H₁₃ and N(CH₂C₆H₅)₂]