4-Nitrophthalamide

Jan, Chin Yee; Shamsudin, Norzianah Binti Haji; Tan, Ai Ling; Young, David J.; Ng, Seik Weng; Tiekink, Edward R. T.

doi:10.1107/s1600536814002955

Cited by 3 publications

(5 citation statements)

References 6 publications

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“…The short bond distances between C1−N2 (1.1394(15) Å) and C2−N3 (1.1429(14) Å) suggest C≡N triple bonds as expected for nitriles. Some of the bond distances and bond angles (Table 1) and the metrical parameters of this compound are similar to those published [21] …”

Section: Resultssupporting

confidence: 75%

“…Hot concentrated H 2 SO 4 generated both phthalic acid and phthalimide as the hydrolysis products [20] . A CoPc has also been reported to undergo photochemical decomposition, and it was discovered that the C−N bonds of the Pc cleave at early stages hence leading to the dissociation of the Pc [21] . The conversion of the Pcs to phthalonitriles in this study was confirmed using FTIR (Figure S2A).…”

Section: Resultssupporting

confidence: 68%

“…[20] A CoPc has also been reported to undergo photochemical decomposition, and it was discovered that the CÀ N bonds of the Pc cleave at early stages hence leading to the dissociation of the Pc. [21] The conversion of the Pcs to phthalonitriles in this study was confirmed using FTIR (Figure S2A). The existence of the carbonitrile group in the hydrolysis products is evident from the obtained FTIR spectra.…”

Section: Rhenium(v)-mediated Hydrolysis Of Pcs and Characterization O...supporting

confidence: 64%

“…Some of the bond distances and bond angles (Table 1) and the metrical parameters of this compound are similar to those published. [21] To further confirm the results of the hydrolysis reactions, GC-MS analysis was carried out (Figures S4 and S5). The MS results of TNPc degradation showed a peak at 173.0 (m/z) which corresponded well with 4-nitrophthalonitrile.…”

Section: Rhenium(v)-mediated Hydrolysis Of Pcs and Characterization O...mentioning

confidence: 98%

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Reaction of Perrhenate with Phthalocyanine Derivatives in the Presence of Reducing Agents and Rhenium Oxide Nanoparticles in Biomedical Applications

et al. 2022

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A novel alternative route to access rhenium(V)−phthalocyanine complexes through direct metalation of metal‐free phthalocyanines (H2Pcs) with a rhenium(VII) salt in the presence of various two‐electron reducing agents is presented. Direct ion metalation of tetraamino‐ or tetranitrophthalocyanine with perrhenate (ReO4−) in the presence of triphenylphosphine led to oxidative decomposition of the H2Pcs, giving their respective phthalonitriles. Conversely, treatment of H2Pcs with ReO4− employing sodium metabisulfite yielded the desired ReVO−Pc complex. Finally, reaction of H2Pcs with ReO4− and NaBH4 as reducing agent led to the formation of rhenium oxide (RexOy) nanoparticles (NPs). The NP synthesis was optimised, and the RexOy NPs were capped with folic acid (FA) conjugated with tetraaminophthalocyanine (TAPc) to enhance their cancer cell targeting ability. The cytotoxicity profile of the resultant RexOy−TAPc−FA NPs was assessed and found to be greater than 80 % viability in four cell lines, namely, MDA−MB‐231, HCC7, HCC1806 and HEK293T. Non‐cytotoxic concentrations were determined and employed in cancer cell localization studies. The particle size effect on localization of NPs was also investigated using confocal fluorescence and transmission electron microscopy. The smaller NPs (≈10 nm) were found to exhibit stronger fluorescence properties than the ≈50 nm NPs and exhibited better cell localization ability than the ≈50 nm NPs.

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Section: Resultssupporting

confidence: 75%

Section: Resultssupporting

confidence: 68%

Section: Rhenium(v)-mediated Hydrolysis Of Pcs and Characterization O...supporting

confidence: 64%

Section: Rhenium(v)-mediated Hydrolysis Of Pcs and Characterization O...mentioning

confidence: 98%

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Reaction of Perrhenate with Phthalocyanine Derivatives in the Presence of Reducing Agents and Rhenium Oxide Nanoparticles in Biomedical Applications

et al. 2022

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“…This crystal morphology is different from the published literature due to crystalization in different experimental condition. This compound was crystallized during the preparation of 3 in the presence of compound 2 and Mn(II) salt in ethanol.…”

Section: Description Of the Crystal Structurescontrasting

confidence: 97%

Functional Substituted Phthalocyanines Bearing Ter–pyridine Complexes as Macromolecular Oxidation Catalysts for Bleaching Systems

et al. 2017

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The present study dealing with the oxidation catalysts using in laundry bleaching process comprises of the complexion of 4’‐(N‐2‐phthalonitrile‐N‐methylamino)‐2,2’:6’,2’’‐terpyridine (2) with the related MnCl2.4H2O and CoCl2.6H2O salts in ethanol to obtain 4’‐(N‐2‐phthalonitrile‐N‐methylamino)‐2,2’:6’,2’’‐terpyridine‐Mn (II) complex (3) and 4’‐(N‐2‐phthalonitrile‐N‐methylamino)‐2,2’:6’,2’’‐terpyridine‐Co (II) complex (4). Terpyridine metal complexes substituted Zinc phthalocyanines, Tetrakis [4’‐(N‐2‐phthalonitrile‐N‐methylamino)‐2, 2’: 6’, 2’’‐terpyridine‐Mn(II) complex] phthalocyaninato zinc(II) (5) and Tetrakis [4’‐(N‐2‐phthalonitrile‐N‐methylamino)‐2,2’:6’,2’’‐terpyridine‐Co(II) complex] phthalocyaninato zinc(II) (6) were also prepared by the tetramerization of the terpyridine‐metal complexes (3, 4) in the presence of ZnCl2. FT‐IR, 1H‐NMR, 13C‐NMR, UV‐Vis, ESI‐MS and MALDI‐MS spectra were applied to characterize the prepared compounds. 4‐nitrophthalonitrile and some other starting materials crystallized in the synthetic pathway. 4‐nitrophthalonitrile crystalizes in different morphology and 4’‐(N‐2‐ Hydroxyehyl‐N‐methylamino)‐2, 2’ : 6’, 2’’‐ terpyridine (1) crystallizes in the monoclinic, space group. The compound 2 and 3 crystallize in the monoclinic space group. The bleach performances of the prepared terpyridine complexes (3, 4) and their phthalocyanine derivatives (5, 6) were examined by the degradation of Morin dye by using online spectrophotometric method (OSM).

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The Oxidation of 4-(4-Formylphenoxy) Phthalonitrile to 4-(4-Carboxylphenoxy) Phthalonitrile at Ambient Conditions

Şen

2019

Cumhuriyet Science Journal

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The substituted phthalonitriles have been used to prepare soluble phthalocyanine species in recent years. One of the most used phthalonitrile derivatives for the target product is 4-nitrophthalonitrile. In this study 4-(4-formylphenoxy) phthalonitrile was prepared as the substituted phthalonitrile derivative by the nucleophilic substitution reaction of para-hydroxybenzaldehyde with 4-nitrophthalonitrile. During the crystallization of the product by slow evaporation technique, it readily self-oxidized to 4-(4-carboxylphenoxy) phthalonitrile at ambient condition open to air. The crystal structure of the molecule was determined by XRD technique. The molecule crystalizes at triclinic space group P-1 and the unit cell parameters of crystal are a=6.3591 (10) Å, b=7.5464 (11) Å, c=13.819 (2) Å, α=88.434 (11)°, β=87.942 (12)°, γ=80.111 (12)° and Z=2. The crystal structure has intermolecular O-H•••O, C-H•••N and C-H•••O hydrogen bonds. In addition to these hydrogen bonds, C-N•••Cg and Cg•••Cg interactions are present between molecules. In the crystal, intermolecular O-H•••O hydrogen bonds occur between molecular units in a dimeric molecular form. Molecular structure, vibrational frequencies and 1 H and 13 C NMR chemical shifts of the target compound have been calculated by using B3LYP method with 6-311++G(d, p) basis set, as well.

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4-Nitrophthalamide

Cited by 3 publications

References 6 publications

Reaction of Perrhenate with Phthalocyanine Derivatives in the Presence of Reducing Agents and Rhenium Oxide Nanoparticles in Biomedical Applications

Reaction of Perrhenate with Phthalocyanine Derivatives in the Presence of Reducing Agents and Rhenium Oxide Nanoparticles in Biomedical Applications

Functional Substituted Phthalocyanines Bearing Ter–pyridine Complexes as Macromolecular Oxidation Catalysts for Bleaching Systems

The Oxidation of 4-(4-Formylphenoxy) Phthalonitrile to 4-(4-Carboxylphenoxy) Phthalonitrile at Ambient Conditions

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