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    Crystal Structure of 4-Bromo-3,4-Dichloro-1-(1-Morpholinyl)-1-(Decylsulfanyl)-2-Nitro-Buta-1,3-Diene
    (Springer/Plenum Publishers, 2010) Ibis, Cemil; Deniz, Nahide Gulsah; Tuyun, Amac Fatih
    The compound 4-bromo-3,4-dichloro-1-(1-morpholinyl)-1-(decylsulfanyl)-2-nitro-buta-3-diene was synthesized from the reaction of 4-bromo-1,3,4-trichloro-1(decylsulfanyl)-2-nitro-buta-1,3-diene with morpholine and characterized by elemental analysis, IR spectrum, UV spectra, H-1 NMR, C-13 NMR and X-ray single crystal determination. In the title compound, C18H29BrCl2N2O3S, crystallizes in the monoclinic space group P2(1)/c, a = 15.8326(4) angstrom, b = 8.9915(10) angstrom, c = 16.7528(5) angstrom, beta = 100.808(10)degrees, V = 2,342.6(3) angstrom(3), Z = 4, R-1 = 0.0590 and wR(2) = 0.0940. The morpholine ring adopts a chair conformation. The morpholine ring and the butadiene group are inclined at an angle of 113.4 (1)degrees. The butadiene unit is not planar as can be expected if the two double bonds are fully conjugated.
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    Extraction equilibria of picolinic acid from aqueous solution by tridodecylamine (TDA)
    (Elsevier, 2011) Tuyun, Amac Fatih; Uslu, Hasan
    Pyridine compounds having a carboxyl side chain at the 2-position are attracting considerable attention for their ability. Chromium, manganese, iron, copper, zinc, and molybdenum are present as chelating agents in the human body. Picolinic acid acts as a chelating agent instead of these elements. In this study, the extraction of picolinic acid was studied using tridodecylamine (TDA) with respect to the functional groups of the diluents. All experiments reported on the extraction of picolinic acid by tridodecylamine (TDA) dissolved in different two different acetates (ethyl acetate and propyl acetate), two different alcohols (1-octanol and 1-decanol), and two different ketones (2-heptanone and 2-octanone), as well as single solvents. The experimental results of batch extraction experiments are reported as distribution coefficients, (K-D = C-PA/C-PA), loading factors, Z, and extraction efficiency, E. All measurements were carried out at 298.15 K. The highest distribution coefficient has been obtained by 1-octanol value of 4.121 and its extraction efficiency is 80%. Linear Solvation Energy Relationship (LSER) model has been applied to the experimental data with good regression coefficient, R-2:0.90. Model results are close to experimental results. (C) 2010 Elsevier B.V. All rights reserved.
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    Extraction of D-(-)-Quinic Acid Using an Amine Extractant in Different Diluents
    (Amer Chemical Soc, 2012) Tuyun, Amac Fatih; Uslu, Hasan
    The extraction of quinic acid was studied by using an amine extractant with respect to the functional groups of the diluents. All experiments were reported on the extraction of quinic acid by tridodecylamine (TDA) dissolved in two different acetates (ethyl acetate and hexyl acetate), two different alcohols (octan-1-ol and decan-1-ol), and two different ketones (heptan-2-one and octan-2-one), as well as single solvents. The experimental results of extraction experiments are reported as distribution coefficients (K-D = (C*(PA)/C-PA)), loading factors, Z, and the extraction efficiency, E. The recovery problem has been reduced by using an amine as an extractant in different diluents. The addition of the extractant was found to improve the extraction.
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    Intensification of Citric Acid Extraction by a Mixture of Trioctylamine and Tridodecylamine in Different Diluents
    (Amer Chemical Soc, 2015) Datta, Dipaloy; Asci, Yavuz Selim; Tuyun, Amac Fatih
    Extraction of citric acid (0.595 mol.kg(-1)) from aqueous solutions has been investigated by using binary extractant system comprising of trioctylamine (TOA) + tridodecylamine (TDA) at six different concentrations (0.19 mol.kg(-1) to 1.16 mol.kg(-1)). The extractant system is diluted using five different solvents such as dimethyl phthalate (DMP), methyl isobutyl ketone (MIBK), 2-octanone, 1-decanol, and cyclohexylacetate (CHA). The batch extraction results of citric acid for the design of a separator have been obtained. The data are interpreted in terms of distribution coefficient (D), loading factors (Z), and extraction efficiency (%E). The values of D for the citric acid extraction are found to vary from 0.40 to 118 for DMP, MIBK, and 2-octanone. For 1-decanol and CHA diluent, the values are observed in the range of 0.38 to 98.16 and 0.39 to 86.76, respectively. Considerable amount of citric acid is recovered (almost 99 %) by all the aminediluent systems at 1.16 mol.kg(-1) initial concentration of (TOA + TDA) mixture.
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    Investigation of Picolinic Acid Extraction by Trioctylamine
    (Berkeley Electronic Press, 2011) Tuyun, Amac Fatih; Uslu, Hasan
    Picolinic acid is a pyridine compound with a carboxyl side chain at the 2-position. It is an isomer of nicotinic acid, which has the carboxyl side chain at the 3-position. Picolinic acid acts as a chelating agent of elements such as chromium, zinc, manganese, copper, iron, and molybdenum in the human body. It is involved in phenylalanine, tryptophan, and alkaloid production, and for the quantitative detection of calcium. In this study, picolinic acid's aqueous solution was extracted by a method reactive extraction. All experiments were reported on the extraction of picolinic acid by trioctylamine (TOA) dissolved in two different aliphatic hydrocarbons (n-octane and n-decane), two different alcohols (octan-1-ol and decan-1-ol), and two different ketones (diisobutyl ketone (DIBK) and octan-2-one), as well as single diluents. Experimental results of batch extraction experiments were calculated and reported as distribution coefficients (K(D)=C(PA)*/C(PA)), loading factors (Z), and extraction efficiency (E). The highest synergistic extraction efficiency was found as 89.199 for TOA+ isoamyl alcohol extractant system with K(D) value of 8.259 and Z value of 0.530.
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    Nucleophilic substitution reactions of 1,4-naphthoquinone and biologic properties of novel S-, S,S-, N-, and N,S-substituted 1,4-naphthoquinone derivatives
    (Springer Birkhauser, 2014) Ibis, Cemil; Tuyun, Amac Fatih; Bahar, Hakan; Ayla, Sibel Sahinler; Stasevych, Maryna V.; Musyanovych, Rostyslav Ya.; Komarovska-Porokhnyavets, Olena
    A novel series of S-, S,S-, N- and N,S-substituted 1,4-naphthoquinone derivatives were synthesized and evaluated for their antibacterial and antifungal activity. Among the synthesized compounds especially 10a and 11b have been discovered as an antibacterial or antifungal agents, and 15f is the most effective compound against M. luteum as potent antifungal. The structures of the novel products were characterized by micro analysis, UV/Vis, H-1 NMR, C-13 NMR, and MS. The electrochemical properties of some of the novel 1,4-naphthoquinone derivatives were also investigated by cyclic voltammetry.
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    Reactive extraction of acrylic acid using trioctylamine (TOA) in versatile diluents
    (Desalination Publ, 2015) Tuyun, Amac Fatih; Uslu, Hasan
    Herein, since the extraction of organic acids is very important for recovery, acrylic acid was investigated from aqueous solutions by different diluents of trioctylamine (TOA). The extraction of acrylic acid with TOA dissolved in various individual solvents has been worked. Solvents have selected as dimethyl phthalate (DMP), cyclohexyleacetate (CHA), methyl isobutyl ketone, 2-octanone, 1-octanol, and 1-decanol. The experimental results of experiments are reported as distribution coefficients, D, loading factors, Z, and extraction efficiency, E. It is essential to improve extraction by adding extractant. The maximum removal of acrylic acid is 97.32% with DMP 1.15 mol/kg initial concentration of TOA. Here in, the LSER model has been applied to TOA + alcohol systems on extraction of acrylic acid to make predictions of distribution coefficient.
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    Reactive Extraction of Cyclic Polyhydroxy Carboxylic Acid Using Trioctylamine (TOA) in Different Diluents
    (Amer Chemical Soc, 2012) Tuyun, Amac Fatih; Uslu, Hasan
    Quinic acid is a cyclic polyhydroxy carboxylic acid compound that is implicated in the perceived acidity of raw materials. It is a constituent of the tannins. In this work, the extraction of quinic acid was studied by using trioctylamine (TOA) with respect to the functional groups. The quinic acid extraction experiments employed TOA + solvent mixtures or pure solvent. The solvents included two acetates, two alcohols, and two ketones. The obtained experimental results of the extraction experiments are reported as distribution coefficients, K-D, loading factors, Z, and extraction efficiencies, E. The highest synergistic extraction efficiency was found to be 83.191 % for the TOA + 1-octanol extractant system, which had a K-D value of 4.949 and a Z value of 0.258.
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    REACTIVITY STUDY OF 2,4-DINITROBUTA-1,3-DIENES TOWARDS MONO-, POLY-, AND PERSULFANYL CONJUGATED DIENES BY REGIOSPECIFIC VINYL GROUP ACTIVATION
    (Taylor & Francis Ltd, 2012) Ibis, Cemil; Tuyun, Amac Fatih
    Polyhalogenated nitrobuta-1,3-dienes are unique reagents in organic synthesis and have been employed in several well-known and recently developed areas of application. This study describes the scope and application of 1,1,3,4-tetrachloro-2,4-dinitrobuta-1,3-diene in organic synthesis as well as methods for the preparation of poly-and perfunctionalized 2,4-initrobuta-1,3-dienes, and characterization of all obtained compounds.
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    Recovery of Picolinic Acid from Aqueous Streams Using a Tertiary Amine Extractant
    (Amer Chemical Soc, 2011) Tuyun, Amac Fatih; Uslu, Hasan; Gokmen, Selahattin; Yorulmaz, Yavuz
    Solvent extraction using an extractant/diluent system was determined for the recovery of picolinic acid. Trioctylamine (TOA) was used as the extractant and alcohols (isoamyl alcohol and 1-hexanol), esters (ethyl acetate and propyl acetate), and hydrocarbons (n-heptane and toluene) as the diluents. TOA gives a complex with the acid resulting in an acid-amine complex which is solvated by the diluents. On the basis of results from batch extraction experiments, a mass-action analysis was introduced for modeling extraction. The experimental results of batch extraction experiments are reported as distribution coefficients, (K(D) = (C*(PA)/C(PA))), loading factors, Z, and extraction efficiency, E. The highest synergistic extraction efficiency was found to be 96.620 for the TOA + isoamyl alcohol extractant system with a K(D) value of 28.587 and Z value of 0.588.
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    Regioselective Substitution of Vinyl Halide by n-Alkyl Mercaptans and Subsequent Reactions with Versatile Cyclic Secondary Amines
    (Asian Journal Of Chemistry, 2010) Ibis, Cemil; Tuyun, Amac Fatih; Aydinli, Goeksin
    Herein, we have described the preparation of several S-subtituted nitrobuta-1,3-dienes (3a-b) using the 4-bromo-1,1,3,4-tetrachloro-2-nitrobuta- 1,3-diene (1) with mercaptans (2a-b). Afterwards, N,S-substituted nitrobuta-1,3-diene compounds (5a, 7b and 9a-j) are obtained from the interaction of versatile secondary amines with the substituted product S-substituted nitrobuta-1,3-dienes (3a-b) in dichloromethane. Synthesized compounds have been characterized by using IR and NMR spectroscopy methods. Structural characterization is supported by elemental analysis and by mass spectrometry with accurate mass measurement of the molecular ion.
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    Spectroscopic and structural aspects of the reactions of 1,4-quinones with sulfur and nitrogen nucleophiles
    (Elsevier France-Editions Scientifiques Medicales Elsevier, 2014) Bayrak, Nilufer; Tuyun, Amac Fatih; Yildirim, Hatice; Onul, Nihal
    A series of 1,4-benzoquinone derivatives from 2,5-dichloro-3,6-diethoxy-1,4-benzoquinone and 2,6-dichloro-3,5-diethoxy-1,4-benzoquinone were prepared by nucleophilic substitution reactions of sulfur and nitrogen nucleophiles. Spectral techniques (H-1 NMR, C-13 NMR, FT-IR, and LC-MS) were employed to structurally characterize the reaction products of alkoxy, chloro substituted-1,4-benzoquinones with thiols and amines in the presence of sodium carbonate in ethanol at room temperature. The orientations and the regioselectivity of the reactions of alkoxy, chloro substituted-1,4-benzoquinones with various thiol and amine nucleophiles are discussed. (C) 2013 Academie des sciences. Published by Elsevier Masson SAS. All rights reserved.
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    Synthesis and Antibacterial and Antifungal Properties of Novel S-, N-, N,S-, and S,O-Substituted 1,4-Naphthoquinone Derivatives
    (Taylor & Francis Ltd, 2013) Ibis, Cemil; Tuyun, Amac Fatih; Ozsoy-Gunes, Zeliha; Ayla, Sibel Sahinler; Stasevych, Maryna V.; Musyanovych, Rostyslav Ya; Komarovska-Porokhnyavets, Olena
    A novel series of substituted 1,4-naphthoquinone derivatives were synthesized and evaluated for their antibacterial and antifungal activity. The structures of the novel products were characterized by spectroscopic methods. Among the tested compounds, 2,2,3,3-alkoxy substituted naphthoquinones, S,O-substituted naphthoquinone, and N,S-substituted naphthoquinone derivatives are the most potent antifungals against C. tenuis. 2,3-Thio-2,3-alkoxy substituted naphthoquinones are the most effective antifungal compounds against A. niger. Supplemental materials are available for this article. Go to the publisher's online edition ofPhosphorus, Sulfur, and Silicon and the Related Elementsto view the free supplemental file.
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    Synthesis and biological evaluation of novel nitrogen- and sulfur-containing hetero-1,4-naphthoquinones as potent antifungal and antibacterial agents
    (Elsevier France-Editions Scientifiques Medicales Elsevier, 2011) Ibis, Cemil; Tuyun, Amac Fatih; Ozsoy-Gunes, Zeliha; Bahar, Hakan; Stasevych, Maryna V.; Musyanovych, Rostyslav Ya.; Komarovska-Porokhnyavets, Olena
    1,4-Naphthoquinones are unique reagents in organic synthesis and have been employed in several well known and recently developed areas of application. Furthermore, these 1,4-naphthoquinones have demonstrated high reactivity in nucleophilic vinylic substitutions, in the preparation of sulfurated, (hetero)cyclic and several other transformations. This study describes the synthesis and biological evaluation of derivatives of monosulfurated naphthalene-1,4-dione (3), 3-chloro-2-ethoxy-naphthalene-1,4-dione (4), disulfurated naphthalene-1,4-dione (5), and symmetrical bis-1,4-naphthoquinones (7, 9) were obtained from the reaction of 2,3-dichloro-naphthaquinone (1) with S-, O-substituted mono-, di-, and tetrathiols, respectively. The structures of the novel products were characterized by spectroscopic methods. Crown Copyright (C) 2011 Published by Elsevier Masson SAS. All rights reserved.
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    The Synthesis of New S- and N,S-Substituted Halo Nitro Dienes by the Reactions of 1-Bromo-1,2,4,4-tetrachloro-3-nitrobuta-1,3-diene with Thiols and Cyclic Amines
    (Taylor & Francis Ltd, 2010) Ibis, Cemil; Tuyun, Amac Fatih; Aydinli, Goksin
    The substituted products alkyl(aryl)thio-tetrahalo-3-nitrobuta-1,3-dienes 3a-b were obtained from the reactions of 1-bromo-1,2,4,4-tetrachloro-3-nitrobuta-1,3-diene (1) with thiols. Further reactions of the substituted product alkyl(aryl)thio-tetrahalo-3-nitrobuta-1,3-dienes 3a-b in dichloromethane reacted with piperazine derivatives and morpholine to generate 5a-b and 7a-l. The structures of the new compounds were determined by microanalysis and spectroscopic data.
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    Synthesis of novel 1,4-naphthoquinone derivatives: antibacterial and antifungal agents
    (Springer Birkhauser, 2013) Ibis, Cemil; Tuyun, Amac Fatih; Bahar, Hakan; Ayla, Sibel Sahinler; Stasevych, Maryna V.; Musyanovych, Rostyslav Ya.; Komarovska-Porokhnyavets, Olena
    A novel series of substituted 1,4-naphthoquinone derivatives was synthesized and evaluated for antibacterial and antifungal activity. The structures of the novel products were characterized by spectroscopic methods. Among the tested compounds, 3a and 9 are the most effective compounds against M. luteum as potent antibacterial and C. tenuis and A. niger as potent antifungal. These two compounds are promising as biologically active compounds.
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    Synthetic exploitation of halogenated alkenes containing an electron-withdrawing group: synthesis of ?-chlorohydrazones and ketene aminals by regiospecific reactions of in situ generated imide chlorides
    (Pergamon-Elsevier Science Ltd, 2014) Tuyun, Amac Fatih
    A concise approach for the construction of ketene aminals and alpha-chlorohydrazones has been developed. It involves reactions of the regiodefined gem-dihalo nitrovinyl compound of in situ generated imide chlorides in different media with primary arylamines being dependent on the aryl groups. A range of ketene aminals and alpha-chlorohydrazones are obtained in good to high yields. In addition, alpha-aminohydrazones are prepared by using alpha-chlorohydrazones as the precursors. (C) 2014 Elsevier Ltd. All rights reserved.
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    SYNTHETIC EXPLOITATION OF HALOGENATED ALKENES CONTAINING ELECTRON-WITHDRAWING GROUP (EWG): ACCESS TO VALUABLE 2,4-DINITROTHIOPHENES VIA RING-CLOSING AND RING-OPENING/RING-CLOSING PROTOCOLS
    (Pergamon-Elsevier Science Ltd, 2013) Tuyun, Amac Fatih
    With the goal of their exploitation for the synthesis of highly functionalized 2,4-dinitrothiophenes, 2-(2,3-dichloro-1,3-dinitroallylidene)-1,3-dithiolane (2), derived from the initial ring-closing of polyhalogenated nitrobutadienic building blocks with 1,2-ethanedithiol, were reacted with secondary amines. After protic work up, highly functionalized 2,4-dinitrothiophenes have been accomplished via ring-opening/ring-closing protocols.
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    Synthetic exploitation of halogenated alkenes containing EWG: benzotriazole-mediated synthesis of benzoazetines and thermal transformations
    (Royal Soc Chemistry, 2014) Tuyun, Amac Fatih
    The series of stable benzoazetine derivatives (5a-d) based on nitrovinyl moieties have been synthesized via transamination of bisbenzotriazolyl derivatives (2a-c). Four new heptatomic aromatic cycloheterocumulenes (azacyclohepta-1,2,4,6-tetraene) occurring at the stage of the film-forming process by TVE have been obtained by rearrangement of benzoazetines. The highly strained products were characterized by IR spectroscopy.