Substitution effects on the structure of o-aryliminophosphoranes

Llamas-Saíz, Antonio L.; Foces‐Foces, C.

doi:10.1107/s0108270193006146

Cited by 4 publications

(3 citation statements)

References 6 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Structural Description of 4-NO 2 -Hpz (1). X-ray diffraction analyses of the ligand revealed that it crystallizes in the neutral form in good agreement with a previous structural solution reported by Llamas-Saiz et al 38 In the structure, there are three crystallographically (A, B, and C) independent 4-NO 2 -Hpz molecules, all of which are protonated at their N1 nitrogen atoms. A remarkable structural feature is that the three ligands are practically planar, finding only a subtle rotation for the nitro group of 0.90−1.74°with regard to the mean aromatic ring.…”

Section: ■ Results and Discussionsupporting

confidence: 88%

Modulating Anticancer Potential by Modifying the Structural Properties of a Family of Zinc Metal–Organic Chains Based on 4-Nitro-1H-pyrazole

Fernández

Cepeda

et al. 2017

Crystal Growth & Design

View full text Add to dashboard Cite

We have synthesized a novel family of metal−organic chains based on 4-nitro-1H-pyrazole linker and zinc as metal center. We report the formation of these coordination polymers using hydrothermal routes with water as solvent. These materials display one-dimensional structures with major structural modifications from minimal synthetic variations. What is more interesting, we have carried out antitumor measurements, and we have related these properties with the structural networks. To the best of our knowledge, these materials constitute the first examples of polymeric structures for 4-NO 2pz ligands. NMR and MS spectrometry were used to verify the characterization of the metal complexes in solution to corroborate that these materials are present in the biological assays.

show abstract

Section: ■ Results and Discussionsupporting

confidence: 88%

Modulating Anticancer Potential by Modifying the Structural Properties of a Family of Zinc Metal–Organic Chains Based on 4-Nitro-1H-pyrazole

Fernández

Cepeda

et al. 2017

Crystal Growth & Design

View full text Add to dashboard Cite

show abstract

“…Since the previously mentioned related triphenyl(phenylimino)phosphoranes all have electrondonating substituents, the typical dimers found in compounds (II) and (III) are absent due to the resulting higher electron density in ring A. Their packing is mainly based on C-HÁ Á Á contacts as in compound (I), althoughinteractions can be found in HATXOP (Llamas-Saiz & Foces-Foces, 1994) and JOZYIG (Llamas-Saiz et al, 1992), and the structure of HATXOP displays C-HÁ Á ÁN interactions.…”

Section: Figurementioning

confidence: 99%

“…In comparison with the two other angles between the P N bond and the rings of the triphenylphosphine group, the N1-P1-C13 angle is much smaller due to the intramolecular C14-H14Á Á ÁN1 interaction, of which the HÁ Á ÁN contact distances and C-HÁ Á ÁN angles are 2.51 Å /108 , 2.51 (2) Å /110 and 2.67 Å /105 for compounds (I), (II) and (III), respectively. This smaller N1-P1-C13 angle can also be found in the structures of related triphenyl(phenylimino)phosphoranes such as the parent triphenyl(phenylimino)phosphorane [refcode GEHRIU (Bohm et al, 1988) in the Cambridge Structural Database (CSD; Allen, 2002)], (2-aminophenylimino)triphenylphosphorane (refcode JOZYIG; Llamas-Saiz et al, 1992), [2-(N,N-dimethylamino)phenylimino]triphenylphosphorane (refcode HATXOP; Llamas-Saiz & Foces- Foces, 1994) and (4-bromophenylimino)triphenylphosphorane (refcode BPITPP; Hewlins, 1971).…”

Section: Commentmentioning

confidence: 99%

Synthesis and structures of substituted triphenyl(phenylimino)phosphoranes

et al. 2009

View full text Add to dashboard Cite

Three substituted triphenyl(phenylimino)phosphoranes, namely (4-cyanophenylimino)triphenylphosphorane, C(25)H(19)N(2)P, (I), (4-nitrophenylimino)triphenylphosphorane, C(24)H(19)N(2)O(2)P, (II), and (3-nitrophenylimino)triphenylphosphorane, C(24)H(19)N(2)O(2)P, (III), were synthesized as precursors for the preparation of substituted diphenylcarbodiimides. All three compounds display a supramolecular arrangement in which the substituted benzene rings are organized in an antiparallel fashion. The nitro group on the ring participates in C-H...O and O...pi interactions, forming intermolecular dimers. Compound (III) shows disorder which involves the rotation of one of the phenyl rings of the triphenylphosphine group.

show abstract

Iminophosphorane-substituted proton sponges. Part 5. Structures in the solid state. Correlation between solid state³¹P MAS NMR spectra and crystal structures

Llamas-Saíz¹,

Foces‐Foces²,

Elguero³

et al. 1994

J. Chem. Soc., Perkin Trans. 2

View full text Add to dashboard Cite

The 31P N M R spectra of protonated iminophosphorane-substituted proton sponges of k n o w n crystal structure have been recorded in the solid state under the conditions of magic angle spinning (MAS) and 'H-decoupling. Variable temperature experiments and a comparison with the averaged 31P chemical shifts in solution show that no proton transfer occurs in the crystal, even when strong intramolecular hydrogen bonds are present. Good agreement between the N M R results and the X-ray structures gives weight to structural predictions based on solid state 31P MAS NMR spectroscopy, for compounds which do not yield suitable monocrystals.

show abstract

Substitution effects on the structure of o-aryliminophosphoranes

Cited by 4 publications

References 6 publications

Modulating Anticancer Potential by Modifying the Structural Properties of a Family of Zinc Metal–Organic Chains Based on 4-Nitro-1H-pyrazole

Modulating Anticancer Potential by Modifying the Structural Properties of a Family of Zinc Metal–Organic Chains Based on 4-Nitro-1H-pyrazole

Synthesis and structures of substituted triphenyl(phenylimino)phosphoranes

Iminophosphorane-substituted proton sponges. Part 5. Structures in the solid state. Correlation between solid state³¹P MAS NMR spectra and crystal structures

Contact Info

Product

Resources

About

Substitution effects on the structure of o-aryliminophosphoranes

Cited by 4 publications

References 6 publications

Modulating Anticancer Potential by Modifying the Structural Properties of a Family of Zinc Metal–Organic Chains Based on 4-Nitro-1H-pyrazole

Modulating Anticancer Potential by Modifying the Structural Properties of a Family of Zinc Metal–Organic Chains Based on 4-Nitro-1H-pyrazole

Synthesis and structures of substituted triphenyl(phenylimino)phosphoranes

Iminophosphorane-substituted proton sponges. Part 5. Structures in the solid state. Correlation between solid state31P MAS NMR spectra and crystal structures

Contact Info

Product

Resources

About

Iminophosphorane-substituted proton sponges. Part 5. Structures in the solid state. Correlation between solid state³¹P MAS NMR spectra and crystal structures