Study on H-bond patterns in phosphoric triamides having a P(O)NHC(O) skeleton, a gauche orientation of P(O) vs C(O) in new compounds

Toghraee, Maryam; Pourayoubi, Mehrdad; Divjaković, Vladimir

doi:10.1016/j.poly.2011.03.045

Cited by 36 publications

(44 citation statements)

References 59 publications

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“…37 A comparison of CeNeC angles in the six-and seven-membered ring systems with an exocyclic CeNeC angle shows that the angle out of the ring is more open than the angle of six-membered ring, and close to the one in the seven-membered ring. For example, the exocyclic CeNeC angle in the structure with the CSD refcode ORISUE, 38 is a few more than 118 . It can thus be concluded that a saturated C atom (sp 3 ) opens the CeCeC angle for self-adaptation in the ring system, while an N atom (sp 2 ) contracts the CeNeC angle in this situation.…”

Section: Puckering Behaviors Of New Structuresmentioning

confidence: 99%

Puckering behavior in six new phosphoric triamides containing aliphatic six- and seven-membered ring groups and a database survey of analogous ring-containing structures

et al. 2018

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The influence of a N heteroatom on the ring conformations of six-and seven-membered aliphatic rings in six new C(O)NHP(O)-based phosphoric triamide structures (analysed by X-ray crystallography) is investigated. Additionally the influence of steric and crystal packing effects is also studied by the analysis of Hirshfeld surfaces. The results are compared to analogous structures with three-to seven-aliphatic membered rings deposited in the Cambridge Structural Database. In the newly determined structures, the six-membered rings only show the near-chair conformation with a maximum deviation of the q puckering parameter of 4.4 from the ideal chair value of 0 /180 , while the seven-membered rings are found in different conformations such as near-chair, twist chair and twist sofa.

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Section: Puckering Behaviors Of New Structuresmentioning

confidence: 99%

Puckering behavior in six new phosphoric triamides containing aliphatic six- and seven-membered ring groups and a database survey of analogous ring-containing structures

et al. 2018

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“…In the crystal, pairs of P OÁ Á ÁH-N hydrogen bonds form inversion dimers with R 2 2 (8) ring motifs. Toghraee et al (2011). For hydrogen-bond strengths in cyclic hydrogen-bond motifs and for bond lengths and angles, see: Pourayoubi et al (2011).…”

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confidence: 99%

N,N′-Dibenzyl-N′′-(2,4-difluorobenzoyl)-N,N′-dimethylphosphoric triamide

et al. 2012

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In the title molecule, C23H24F2N3O2P, the P atom is in a distorted tetrahedral P(=O)(N)(N)2 environment, with the bond angles around the P atom in the range 106.78 (11)–114.10 (13)°. The phosphoryl and carbonyl groups, which are separated by an N atom, adopt an anti orientation relative to each other. In the C(=O)NHP(=O) fragment, the P—N bond is longer [1.683 (2) Å] and the O—P—N angle is smaller [106.78 (11)°] than the other P—N bonds [1.613 (2) and 1.632 (2) Å] and O—P—N bond angles [114.10 (13) and 110.83 (12)°], respectively. The N atoms have sp 2 character. In the crystal, pairs of P=O⋯H—N hydrogen bonds form inversion dimers with R 2 2(8) ring motifs.

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“…In both structures, the O=P-N CP angles are smaller than the two O=P-N P angles, Table 3 (in our discussion, the N CP is used for the nitrogen atom within the C(O)NHP(O) segment and the N P is representation of two other nitrogen atoms attached to the phosphorous atom). The P=O and C=O bond lengths [respectively, 1.464(3) Å and 1.235(6) Å for 1 and 1.4734(11) Å and 1.228(2) Å for 2] are in the standard range for phosphoric triamides (Toghraee et al 2011). The sixmembered P1/N1/C3/C2/C1/N2 ring of 1 adopts a nearly half-boat conformation on the basis of puckering parameters calculated according to Cremer and Pople (1975) [Q = 0.500(6), θ = 155.1(6)°, Φ = 13.9(14)°].…”

Section: General Structural Featuresmentioning

confidence: 99%

“…The reasons for such interests are not only because they may be considered as small molecular models of some biologically active macromolecules such as phosphorus-nitrogen compounds like tetrapeptide-based phosphoramides (Wu and Hu 2016), but also because there are many examples of biologically active phosphoramide small molecules (Upadhyay, 2012). On the other hand, the basic skeleton in the phosphoramide compounds, P(=O)(N), is similar to the group occurring in peptides, (C=O)(N), and some similarity was found on the properties (Yizhak et al 2013) with differences arising from the tetrahedral environment in phosphorus and the planar environment in carbon, and also the greater electron-donor capability of P=O with respect to C=O (Toghraee et al 2011). Moreover, the study of intermolecular interactions received by a phosphoramide small molecule is interesting, as they are usually similar to the case where such a molecule is placed in a biological environment such as an enzyme's active site (Carletti et al 2013).…”

Section: Introductionmentioning

confidence: 98%

Different molecular assemblies in two new phosphoric triamides with the same C(O)NHP(O)(NH)2 skeleton: crystallographic study and Hirshfeld surface analysis

et al. 2017

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Different molecular assemblies were compared in two new structures [4-CH 3 -C 6 H 4 C(O)NH]P(O) [NH] 2 (-CH 2 ) 3 , 1, and [4-CH 3 -C 6 H 4 C(O)NH]P(O) [NHC 6 H 3 (3, ) 2 ] 2 , 2, belonging to the families of "cyclic phosphoric triamide" and "phosphoric triamide", respectively. The differences in the hydrogen bond motifs were discussed (by single crystal X-ray diffraction) as a result of three factors: (1) action of two N atoms with a non-planar environment in 1 as an H-bond acceptor, (2) different orientations of three N-H bond vectors in two molecules and (3) different conformations of C=O and P=O groups. These differences lead to more complicated hydrogen bond pattern of 1, with respect to that of 2, as structure 1 may be considered as a model of four-acceptor-three-donor versus a two-acceptorthree-donor system in 2. The main discrepancies of 1 and 2, monitored by the Hirshfeld surface analysis, are related to the contribution portions of O···H/H···O contacts, in which compound 1 not only involves the greater existence of classical hydrogen bonds but also contains the further C-H···O weak interactions in its crystal packing with respect to compound 2. Instead, in 2, the shortage of O···H/H···O contacts has been partially compensated by the C···H/H···C interactions, due to the presence of more unsaturated carbon acceptors. The differences in assemblies are also reflected in the solid-state IR spectra, especially for the N-H vibration frequencies. The new compounds were further studied by 1D NMR experiments ( 1 H, 13 C, 31 P), 2D NMR techniques [HMQC and HMBC (H-C correlation), HSQC (N-H correlation)], high-resolution ESI-MS, EI-MS spectrometry and IR spectroscopy.

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Study on H-bond patterns in phosphoric triamides having a P(O)NHC(O) skeleton, a gauche orientation of P(O) vs C(O) in new compounds

Cited by 36 publications

References 59 publications

Puckering behavior in six new phosphoric triamides containing aliphatic six- and seven-membered ring groups and a database survey of analogous ring-containing structures

Puckering behavior in six new phosphoric triamides containing aliphatic six- and seven-membered ring groups and a database survey of analogous ring-containing structures

N,N′-Dibenzyl-N′′-(2,4-difluorobenzoyl)-N,N′-dimethylphosphoric triamide

Different molecular assemblies in two new phosphoric triamides with the same C(O)NHP(O)(NH)2 skeleton: crystallographic study and Hirshfeld surface analysis

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