A fluorine nuclear magnetic resonance shielding study of substituent effects on charge distributions in benzophenone and its Lewis acid adducts

Pews, R. G.; Tsuno, Yuho; Taft, Robert W.

doi:10.1021/ja00986a026

Cited by 38 publications

(14 citation statements)

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“…In a previous study, a methoxy‐terminated initiator has been used with success to prepare low molecular weight telechelic polycondensation PES, although transetherification reactions limited the maximum molar mass which could be obtained . In the present work, two methods previously used in the literature helped in initiator selection: Semi‐empirical calculations and 19 F NMR study of the aromatic fluorine reactivity . Both methods led to the same conclusion, and a methoxy‐terminated initiator was selected .…”

Section: Resultsmentioning

confidence: 73%

Soluble Telechelic Polycondensation Poly(ether ketones): Synthesis and Characterization

Benhalima

Fürtös

Brisson

2019

Macro Chemistry & Physics

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The present article reports the synthesis of soluble, propyl‐substituted aromatic ring telechelic polycondensation blocks having molecular weights ranging from 1800 to 6500 g mol−1 and polymolecularities of 1.3 to 1.7. Chain‐growth polycondensation is performed, and the initiator is selected through reactivity studies, using 19F nuclear magnetic resonance (NMR) measurements. Gel permeation chromatography, NMR spectroscopy, and matrix‐assisted laser desorption/ionization time of flight mass spectrometry show that blocks are terminated by a methoxy group at one end and a fluorine atom at the other. Polymers are crystalline as synthesized, as shown by X‐ray diffraction and differential scanning calorimetry, do not recrystallize once melted, and undergo solvent‐induced crystallization. Crystalline peak positions and relative intensities are different from those observed for other poly(ether ketones). The difference in crystal form is proposed to stem from packing disruption related to the presence of propyl substituents. Thermogravimetry shows a good thermal resistance up to 450 °C.

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Section: Resultsmentioning

confidence: 73%

Soluble Telechelic Polycondensation Poly(ether ketones): Synthesis and Characterization

Benhalima

Fürtös

Brisson

2019

Macro Chemistry & Physics

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“…The target compound B5 was synthesized by condensation of 4-benzyloxyaniline and intermediate 1, followed by cleavage of the benzyl group catalyzed with Pd-C [25] . Compounds A8-10 and B10-12 were prepared by condensation of the intermediate 1 with intermediates 4-halo-4'-hydroxybenzophenone or 4-amino-4'-halobenzophenone, respectively [26,27] . Compounds A12-14 and B14-16 were prepared by condensation of the intermediate 1 with intermediate 4-halo-4'-hydroxy- diphenyl or 4-amino-4'-halodiphenyl, respectively [28][29][30] .…”

Section: Methodsmentioning

confidence: 99%

Derivatives of aryl-4-guanidinomethylbenzoate and N-aryl-4-guanidinomethylbenzamide as new antibacterial agents: synthesis and bioactivity

Yang

Xie³

et al. 2008

Acta Pharmacologica Sinica

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Aim: The aim of the present study was to design, synthesize, and evaluate novel antibacterial agents, derivatives of aryl-4-guanidinomethylbenzoate and N-aryl-4-guanidinomethylbenzamide. Methods: A total of 44 derivatives of aryl-4-guanidinomethylbenzoate (series A) and N-aryl-4-guanidinomethylbenzamide (series B) were synthesized and their antibacterial activities were assessed in vitro against a variety of Gram-positive and Gram-negative bacteria by an agar dilution method. Results: Twelve compounds showed potent bactericidal effects against a panel of Gram-positive germs, including methicillin-resistant Staphylococcus aureus (MRSA), vancomycin-resistant enterococci (VRE), vancomycin-intermediate Staphylococcus aureus (VISA), and methicillin-resistant coagulase-negative staphylococci (MRCNS), with minimum inhibitory concentrations (MIC) ranging between 0.5 and 8 µg/mL, which were comparable to the MIC values of several marketed antibiotics. They exhibited weak or no activity on the Gram-negative bacteria tested. In addition, these compounds displayed high inhibitory activities towards oligopeptidase B of bacterial origin. Conclusion: In comparison with the previously reported MIC values of several known antibiotics, the derivatives of aryl-4-guanidinomethylbenzoate and N-aryl-4-guanidinomethylbenzamide showed comparable in vitro bactericidal activities against VRE and VISA as linezolid. Their growth inhibitory effects on MRSA were similar to vancomycin, but were less potent than linezolid and vancomycin against MRCNS. This class of compounds may have the potential to be developed into narrow spectrum antibacterial agents against certain drug-resistant strains of bacteria.

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“…Some of them are utilized as highly performed functional compounds for optoelectronic devices such as liquid crystalline molecules [18][19][20] and non-linear optical materials 21) . As the simplest compound of this species, 4-fluoro-4'-trifluoromethylbenzophenone ( ) possesses characteristic electronic structure [22][23][24][25] and show unique chemical and physical behaviors. It has been utilized as a coating agent for toner-supplying part in one-component electrophotographic developing apparatus [26][27][28] , a synthetic precursor for antimalarial radiopharmaceutical guanylhydrazones 29,30) , and an effective initiator for nucleophilic aromatic substitution polymerization giving monodispersed poly(aromatic ether ketone)s [31][32][33] .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Novel Trifluoromethyl-bearing Bifunctional Acyl-acceptant Arenes: 2,2'-Bis(trifluoromethylated aryloxy)biphenyls

et al. 2007

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Novel bifunctional acyl-acceptant biphenyls bearing trifluoromethylated aroyloxy groups were successfully synthesized in high yields via TfOH-mediated electrophilic aromatic aroylation of fluorobenzene with CF 3 -bearing aroyl chlorides followed by nucleophilic aromatic substitution with 2,2'-biphenol. Similarly, 2,2'-bis(trifluoromethylphenoxy)biphenyl was synthesized via nucleophilic aromatic substitution of 4-fluorobenzotrifluoride with 2,2'-biphenol. These 2,2'-bis(trifluoromethylated aryloxy)biphenyls show good regioselectivity and successive reactivity in electrophilic aromatic aroylation with p-toluic acid/p-toluoyl chloride according to the structure of the substrate biphenyls, implying their sufficient potential as acyl-accepting precursor molecules for synthesis of aromatic compounds bearing characteristic interfacial properties attributed to CF 3 groups.

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A fluorine nuclear magnetic resonance shielding study of substituent effects on charge distributions in benzophenone and its Lewis acid adducts

Cited by 38 publications

References 0 publications

Soluble Telechelic Polycondensation Poly(ether ketones): Synthesis and Characterization

Soluble Telechelic Polycondensation Poly(ether ketones): Synthesis and Characterization

Derivatives of aryl-4-guanidinomethylbenzoate and N-aryl-4-guanidinomethylbenzamide as new antibacterial agents: synthesis and bioactivity

Synthesis of Novel Trifluoromethyl-bearing Bifunctional Acyl-acceptant Arenes: 2,2'-Bis(trifluoromethylated aryloxy)biphenyls

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