Combined experimental and theoretical approaches to the molecular structure of 4-(1-formylnaphthalen-2-yloxy)phthalonitrile

Tereci, Hidayet; Askeroğlu, İskender; Akdemir, Nesuhi; Uçar, İbrahim; Büyükgüngör, Orhan

doi:10.1016/j.saa.2012.07.005

Cited by 9 publications

(3 citation statements)

References 26 publications

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“…In addition, the coupling of 2‐hydroxybenzaldehyde with 4‐nitrophthalonitrile ended in poor yield and relatively low purity (entry 13), and complex by‐products were discovered. This indicated that aldehyde group was not so stable under such reaction condition, which is similar to previous reports …”

Section: Resultssupporting

confidence: 92%

Activated‐Carbon‐Supported Calcium Oxide: A Selective and Efficient Catalyst for Nitrile‐Containing Diaryl Ether Synthesis

et al. 2018

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Activated-carbon-supported calcium oxide (CaO@AC) was prepared from AC and a suspension derived from CaO and ammonium carbonate. After calcination under nitrogen, high purity CaO@AC was obtained. The nature of non-aggregation and high purity of CaO@AC enabled a clean and selective synthesis protocol for nitrile-containing diaryl ethers. Various functional groups including methoxyl, amino, carboxyl, allyl and nitro were well-tolerated, and products were obtained in excellent yields and purities. Asymmetric substitutions could be achieved via simple adjustment of reaction conditions, and transetherification was greatly suppressed to 10 À 3 -10 À 4 scale. In addition, a mechanism for suppression in transetherification was proposed and discussed.

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Section: Resultssupporting

confidence: 92%

Activated‐Carbon‐Supported Calcium Oxide: A Selective and Efficient Catalyst for Nitrile‐Containing Diaryl Ether Synthesis

et al. 2018

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“…basis sets[42] in other DFT studies containing phthalonitrile group, and results are in agreement with typical carbon-nitrogen triple bond (about 1.16 Å). The lengths of carbonoxygen bond which serves as a bridge between phthalonitrile and trimethylbenzene groups are 1.359 and 1.403 Å, theoretically, 1.36, 1.44 Å for 6-31G(d) basis set in another study[43].…”

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confidence: 87%

Synthesis, characterization and investigation of the spectroscopic properties of novel peripherally 2,3,5-trimethylphenoxy substituted Cu and Co phthalocyanines, the computational and experimental studies of the 4-(2,3,5-trimethylphenoxy)phthalonitrile

Akdemir¹

2016

Journal of the Turkish Chemical Society, Section A: Chemistry

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4-(2,3,5-trimethylphenoxy)phthalonitrile (3) was prepared via aromatic nucleophilic substitution reaction and characterized by FT-IR, mass spectrometry, 1 H and 13 C NMR techniques. The molecular structure of compound (3) was optimized using Density Functional Theory (DFT/B3LYP) method with 6-311G(d,p) basis set in the ground state. The molecular geometric parameters which were obtained by X-ray single crystal diffraction method and the spectral results were compared with computed bond lengths and angles, vibrational frequencies, and

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“…The two cyano groups deviate from this plane by 0.0870 (15) and −0.0711(17) Å at atoms N1 and N2, [32][33][34][35]. At the same time, the C≡N bond lengths have been calculated using B3LYP method with 6-311++G(dp) basis set and this bonds were found as: 1.155 Å and 1.154 Å, respectively.…”

Section: Description Of the Crystal Structurementioning

confidence: 99%

The Synthesis, Characterization, Crystal Structure and Photophysical Properties of a New Meso-BODIPY Substituted Phthalonitrile

et al. 2015

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A b s t r a c t A n e w h i g h l y f l u o r e s c e n t difluoroboradipyrromethene (BODIPY) dye (4) bearing an phthalonitrile group at meso-position of the chromophoric core has been synthesized starting from 4-(4-mesodipyrromethene-phenoxy)phthalonitrile (3) which was prepared by the oxidation of 4-(2-meso-dipyrromethanephenoxy)phthalonitrile (2). The structural, electronic and photophysical properties of the prepared dye molecule were investigated. The final product exhibit noticeable spectroscopic properties which were examined by its absorption and fluorescence spectra. The original compounds prepared in the reaction pathway were characterized by the combination of FT-IR, 1 H and 13 C NMR, UV-vis and MS spectral data. It has been calculated; molecular structure, vibrational frequencies, 1 H and 13 C NMR chemical shifts and HOMO and LUMO energies of the title compound by using B3LYP method with 6-311++G(dp) basis set, as well. The final product (4) was obtained as single crystal which crystallized in the triclinic space group P-1 with a=9.0490 (8) Å, b=10.5555 (9) Å, c= 11.7650 (9) Å, α=77.024 (6)°, β=74.437 (6)°, γ=65.211 (6)°a nd Z=2. The crystal structure has intermolecular C-H···F weak hydrogen bonds. The singlet oxygen generation ability of the dye (4) was also investigated in different solvents to determine of using in photodynamic therapy (PDT).

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Combined experimental and theoretical approaches to the molecular structure of 4-(1-formylnaphthalen-2-yloxy)phthalonitrile

Cited by 9 publications

References 26 publications

Activated‐Carbon‐Supported Calcium Oxide: A Selective and Efficient Catalyst for Nitrile‐Containing Diaryl Ether Synthesis

Activated‐Carbon‐Supported Calcium Oxide: A Selective and Efficient Catalyst for Nitrile‐Containing Diaryl Ether Synthesis

Synthesis, characterization and investigation of the spectroscopic properties of novel peripherally 2,3,5-trimethylphenoxy substituted Cu and Co phthalocyanines, the computational and experimental studies of the 4-(2,3,5-trimethylphenoxy)phthalonitrile

The Synthesis, Characterization, Crystal Structure and Photophysical Properties of a New Meso-BODIPY Substituted Phthalonitrile

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