Synthesis, Spectroscopic Study and Crystal Structure of a New Amidophosphonate, (C&lt;sub&gt;6&lt;/sub&gt;H&lt;sub&gt;5&lt;/sub&gt;O)&lt;sub&gt;2&lt;/sub&gt;P(O)(NHCH(CH&lt;sub&gt;3&lt;/sub&gt;)(C&lt;sub&gt;2&lt;/sub&gt;H&lt;sub&gt;5&lt;/sub&gt;))

Hamzehee, Farahnaz; Pourayoubi, Mehrdad; Choquesillo‐Lazarte, Duane

doi:10.2116/xraystruct.32.47

Cited by 2 publications

(3 citation statements)

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“…Selected geometric parameters and hydrogen-bond geometries are given in Tables 2-4. The P O, P-O and P-N bond lengths are within the ranges observed in analogous structures (Hamzehee et al, 2016). The P-N-C and P-O-C angles show a little more 's' character with respect to sp 2 hybridization, as has been reported previously by a Cambridge Structural Database (CSD) analysis and by quantum chemical calculations for analogous structures (Sabbaghi et al, 2016;Vahdani Alviri et al, 2018).…”

Section: Description Of the Crystal Structuressupporting

confidence: 85%

“…For both (I) and (II), the 31 P signal appears at À0.81 ppm, in comparison with the value of 0.05 ppm for the analogous (C 6 H 5 O) 2 P(O)[NHCH(CH 3 )(C 2 H 5 )] compound (Hamzehee et al, 2016).…”

Section: Spectroscopic Studymentioning

confidence: 71%

“…Amidophosphoesters are also interesting for purely scientific studies, for example, the investigation of phosphorushydrogen and phosphorus-carbon NMR coupling constants, with examples of short-range 2,3 J P-H and long-range 6,7 J P-H coupling constants having been reported (Gholivand et al, 2001(Gholivand et al, , 2005a. Differences in the chemical shifts and coupling constants associated with the diastereotopic groups have also been reported (Gholivand et al, 2005b;Hamzehee et al, 2016).…”

Section: Introductionmentioning

confidence: 99%

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Two single-enantiomer amidophosphoesters: a database study on the chirality of (O)₂P(O)(N)-based structures

et al. 2019

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The crystal structures of two single-enantiomer amidophosphoesters with an (O) 2 P(O)(N) skeleton, i.e. diphenyl [(R)-(+)--methylbenzylamido]phosphate, (I), and diphenyl [(S)-(À)--methylbenzylamido]phosphate, (II), both C 20 H 20 -NO 3 P, are reported. In both structures, chiral one-dimensional hydrogenbonded architectures, along [010], are mediated by N-HÁ Á ÁOP interactions. The statistically identical assemblies include the noncentrosymmetric graph-set motif C(4) and the compounds crystallize in the chiral space group P2 1 . As a result of synergistic co-operation from C-HÁ Á ÁO interactions, a two-dimensional superstructure is built including a noncentrosymmetric R 4 4 (22) hydrogenbonded motif. A Cambridge Structural Database survey was performed on (O) 2 P(O)(N)-based structures in order to review the frequency of space groups observed in this family of compounds; the hydrogen-bond motifs in structures with chiral space groups and the types of groups inducing chirality are discussed. The 2,3 J X-P (X = H or C) coupling constants from the NMR spectra of (I) and (II) have been studied. In each compound, the two diastereotopic C 6 H 5 O groups are different, which is reflected in the different chemical shifts and some coupling constants.

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Section: Description Of the Crystal Structuressupporting

confidence: 85%

Section: Spectroscopic Studymentioning

confidence: 71%

Section: Introductionmentioning

confidence: 99%

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Two single-enantiomer amidophosphoesters: a database study on the chirality of (O)₂P(O)(N)-based structures

et al. 2019

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Investigation of crystal structures, energetics and isostructurality in halogen-substituted phosphoramidates

Hasija¹,

Som²,

Chopra³

2022

Acta Crystallogr Sect B

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A total of 14 compounds, one unsubstituted and 13 halogen-substituted phosphoramidates, have been synthesized from unsubstituted and halogenated (fluoro-, difluoro-, chloro-, bromo-, iodo-substituted) aniline and diphenyl phosphoryl chloride to investigate their molecular assembly in solid-state structures. Amongst them, six groups were formed based on similarities in unit-cell dimensions, space group and molecular assembly of the crystal. The analysis reveals that all the crystal structures contain robust N—H...O hydrogen bonds which are the primary building blocks with ancillary interactions such as C—H...O, C—H...π, C—H...F/Cl/Br/I, F...F, F...π, I...π, Br...π, I...O and Br...O. The role of short and directional C—H...O and C—H...π interactions providing significant stabilization to the densely packed crystalline arrangement is discussed. The contribution of these interactions in stabilizing the crystalline assembly was deduced via computing total interaction energy between dimers and the overall lattice energies using the computer programs Crystal Explorer 17.5 and PIXELC, respectively. Additionally, the occurrence of 3D isostructurality in phosphoradimates and their halogenated analogs was investigated using the XPac program. A comparison of the magnitudes of the torsion angles in the compounds substantiates the role of conformational flexibility in the solid state.

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Synthesis, Spectroscopic Study and Crystal Structure of a New Amidophosphonate, (C<sub>6</sub>H<sub>5</sub>O)<sub>2</sub>P(O)(NHCH(CH<sub>3</sub>)(C<sub>2</sub>H<sub>5</sub>))

Cited by 2 publications

References 8 publications

Two single-enantiomer amidophosphoesters: a database study on the chirality of (O)₂P(O)(N)-based structures

Two single-enantiomer amidophosphoesters: a database study on the chirality of (O)₂P(O)(N)-based structures

Investigation of crystal structures, energetics and isostructurality in halogen-substituted phosphoramidates

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Synthesis, Spectroscopic Study and Crystal Structure of a New Amidophosphonate, (C<sub>6</sub>H<sub>5</sub>O)<sub>2</sub>P(O)(NHCH(CH<sub>3</sub>)(C<sub>2</sub>H<sub>5</sub>))

Cited by 2 publications

References 8 publications

Two single-enantiomer amidophosphoesters: a database study on the chirality of (O)2P(O)(N)-based structures

Two single-enantiomer amidophosphoesters: a database study on the chirality of (O)2P(O)(N)-based structures

Investigation of crystal structures, energetics and isostructurality in halogen-substituted phosphoramidates

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Two single-enantiomer amidophosphoesters: a database study on the chirality of (O)₂P(O)(N)-based structures

Two single-enantiomer amidophosphoesters: a database study on the chirality of (O)₂P(O)(N)-based structures