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How to cite this paper
APA: Dresler, E., Nowakowska-Bogdan, E., Łącka, W., Ząbkowska, M., Kapuściński, D & Jasiński, R. (2025). Electronic properties of complexes derived from imidazolium cations and carbonyl compounds and their reactivity in synthesis of bisphenol derivatives in the light of CDFT/MEDT approach. Current Chemistry Letters, 14(4), 771-776.
Chicago/Turabian: Dresler, E., Nowakowska-Bogdan, E., Łącka, W., Ząbkowska, M., Kapuściński, D & Jasiński, R. 2025. "Electronic properties of complexes derived from imidazolium cations and carbonyl compounds and their reactivity in synthesis of bisphenol derivatives in the light of CDFT/MEDT approach." Current Chemistry Letters 14, no. 4 (2025): 771-776.
AMA: Dresler, E., Nowakowska-Bogdan, E., Łącka, W., Ząbkowska, M., Kapuściński, D & Jasiński, R. Electronic properties of complexes derived from imidazolium cations and carbonyl compounds and their reactivity in synthesis of bisphenol derivatives in the light of CDFT/MEDT approach. Current Chemistry Letters. 2025;14(4):771-776.
References
1 Nowakowska-Bogdan E., Wicher E., Ochędzan-Siodłak W. and Dziubek K. (2009) Condensation of phenol with ethyl levulinate in acidic 1-n-alkyl-3-methylimidazolium ionic liquids. Przem. Chem., 88, 1058-1062
2 Nowakowska-Bogdan E., Dresler E. (2012) Optimization of conditions of condensation of phenol with methyl pyruvate in acidic 1-n-butyl-3-methylimidazolium aluminium chloride ionic liquid medium. Przem. Chem., 91, 1931-1934
3 Nowakowska-Bogdan E. and Dresler E. (2013) Condensation of phenols with methylpyruvate in 1-n-butyl-3-methylimidazolium aluminium chloride ionic liquid medium. Przem. Chem., 92, 1868-1871
4 Dresler E., Nowakowska-Bogdan E., Kulesza R., and Jasiński R. (2013) Temperature and solvent effect on the thermodynamic equilibrium in the intramolecular transesterification process of ethyl 4-(4-hydroxyphenyl)-4-(2-hydroxyphenyl)-pentanoate. Przem. Chem., 92, 1876-1878
5 Wang C.H. and Nakamura S. (1995) Synthesis of aromatic polyesters having pendant carboxyl groups in the side chains and conversion of the carboxyl groups to other reactive groups. J. Polym. Sci. Part A Polym. Chem. 33, 2157-2163
6 Rodewald B. and Ritter H. (1999) Oligo(ether sulfones). 3.† Block Copolymers via Condensation Reactions of Telechelic Oligo(ether sulfones) Bearing Phenolic Endgroups and Oligomeric r,ö-Diols. Macromolecules, 32, 1697-1700
7 Gong C. and Fréchet J.M.J., (2000) Proton Transfer Polymerization in the Preparation of Hyperbranched Polyesters with Epoxide Chain-Ends and Internal Hydroxyl Functionalities. Macromolecules, 33, 4997-4999
8 Park D.W., Ha D.H., Park J.Y., Moon J.Y. and Lee H.S. (2001) Synthesis of aromatic polyesters bearing pendant carboxyl groups by phase transfer catalysis. React. Kinet. Catal. Lett., 72, 219-227
9 Zhang R.F. and Moore J.A. (2002) Synthesis, Characterization and Properties of Polycarbonate Containing diphenolic acid. Polym. Prepr., 43, 1007-1008
10 Kim K.H., Moon J.Y., Ha D.H., and Park D.W. (2002) Synthesis of aromatic polyesters using polymeric catalysts having quaternary ammonium salt groups. React. Kinet. Catal. Lett., 75, 385-395
11 Zhang R. F. and Moore J.A. (2003) Synthesis, Characterization and Properties of Polycarbonate Containing Carboxyl Side Groups. Macromol. Symp. 199, 375-390
12 Calò E., Maffezzoli A., Mele G., Martina F., Mazetto S.E., Tarzia A. and Stifani C. (2007) Synthesis of a novel cardanol-based benzoxazine monomer and environmentally sustainable production of polymers and bio-composites. Green Chem., 9, 754-759
13 Zhang P., Wu L., Bu Z. and Li B.G. (2008) Interfacial Polycondensation of Diphenolic Acid and Isophthaloyl Chloride. J. Appl. Polym. Sci., 108, 3586-3592
14 Zhang P., Wu L. and Li B.G. (2009) Thermal stability of aromatic polyesters prepared from diphenolic acid and its esters. Polym. Degrad. Stab., 94, 1261–1266
15 Lochab B., Varma I.K. and Bijwe J. (2010) Thermal behaviour of cardanol-based benzoxazines. Therm. Calorim., 102, 769-774
16 Liu Y., Zhang Y. and Fang Z. (2012) Design, synthesis, and application of novel flame retardants derived from biomass. Bioresour., 7, 4914-4925
17 Zúñiga C., Lligadas G., Ronda J.C., Galià M. and Cádiz V. (2012) Self-foaming diphenolic acid benzoxazine. Polymer, 53 , 3089-3095
18 Hiratsuka Y., Funaya N., Matsunaga H., Haginaka J. (2013) Preparation of magnetic molecularly imprinted polymers for bisphenol A and its analogues and their application to the assay of bisphenol A in river water. J. Pharm. Biomed. Anal., 75, 180-185
19 Peng C., Wu J., Liu J., Qiu L., Liu X., Bo S. and Zhen Z. (2013) Synthesis and optical properties of new fluorinated second-order nonlinear optical copolymers: an attempt toward the balance between solubility and long-term alignment stability. Polym. Chem., 4, 2703-2708
20 Zúñiga C., Larrechi M.S., Lligadas G., Ronda J.C., Galià M. and Cádiz V. (2011) Polybenzoxazines from Renewable Diphenolic Acid. J. Polym. Sci., Part A: Polym. Chem., 49, 1219-1227
21 Zúñiga C., Lligadas G., Ronda J.C., Galià M. and Cádiz V. (2012) Renewable polybenzoxazines based in diphenolic acid. Polymer, 53, 1617-1623
22 Łapczuk-Krygier A., Baranowska K., Ponikiewski L., Matern E., Pikies J. (2012) π-Indenyl substituted zirconium compounds containing terminal bonded phosphanylphosphido ligands. Inorganica Chimica Acta, 387, 361 - 365
23 T. Kolasa et al. (2000) Symmetrical Bis(heteroarylmethoxyphenyl)alkylcarboxylic Acids as Inhibitors of Leukotriene Biosynthesis. J. Med. Chem., 43, 3322-3334
24 Hai-Feng L., Fan-Xin Z., Li D., Bing L., Hao P., Quin-Xiang G. (2013) Brønsted acidic ionic liquids catalyze the high-yield production of diphenolic acid/esters from renewable levulinic acid. Green Chem., 15, 81-84
25 Plechkova N.V and Seddon K.R. (2008) Applications of ionic liquids in the chemical industry. Chem. Soc. Rev., 37 (2008), 123-150
26 Yue C., Fang D., Liu L. and Yi T.F. (2011) Synthesis and application of task-specific ionic liquids used as catalysts and/or solvents in organic unit reactions. J. Mol. Liq., 163, 99–121
27 Khaligh N.G. (2012) Synthesis of coumarins via Pechmann reaction catalyzed by 3-methyl-1-sulfonic acid imidazolium hydrogen sulfate as an efficient, halogen-free and reusable acidic ionic liquid. Catal. Sci. Technol., 2, 1633-1636
28 Shaterian H. R. and Aghakhanizadeh M. (2013) Ionic-liquid-catalyzed green synthesis of coumarin derivatives under solvent-free conditions. Chinese J. Catal., 34, 1690–1696
29 Ghosh P.K., Guha T. and Saha A.N. (1967) Kinetic study of formation of bisphenol a. J. Appl. Chem., 17, 239- 240
30 Pérez P., Domingo L.R., Aizman A. and Contreras R. (2008) The electrophilicity index in organic chemistry. Theor. Aspects Chem. React., 19, 139-201
31 Domingo L.R., Aurell M.J., Perez P. and Contreras R. (2002) Quantitative characterization of the global electrophilicity power of common diene/dienophile pairs in Diels-Alder reactions. Tetrahedron, 58, 4417-4423
32 Chattaraj P.K., Giri S. and Duley S. (2011) Electrophilicity Index. Chem. Rev., 111, PR43-PR75
33 Domingo L.R. (2024) 1999 – 2024, a Quarter Century of the Parr’s Electrophilicity ω Index. Scientiae Radices, 3(3), 156-186
34 Fryźlewicz A., Olszewska A., Zawadzińska K., Woliński P., Kula K., Kącka-Zych A., Łapczuk-Krygier A. and Jasiński R. (2022) On the Mechanism of the Synthesis of Nitrofunctionalised Δ2-Pyrazolines via [3+2] Cycloaddition Reactions between α-EWG-Activated Nitroethenes and Nitrylimine TAC Systems. Organics, 3(1), 59 - 76
35 M.J. Frisch et al. (2009) Gaussian 09 rev A.1 Gaussian, Inc. Wallingford CT
36 Parr R.G. and Yang W. (1989) Density Functional Theory of Atoms and Molecules. Oxford University, New York
37 Sadowski M., Dresler E., Zawadzinska-Wrochniak K., Wroblewska A., and Jasinski R. (2024) Syn-propanethial S-oxide as the natural available building block for the preparation of nitrofunctionalized sulfur containing five-membered heterocycles: MEDT study. Molecules, 29, 4892
38 Łapczuk-Krygier A., Korotaev V.Y., Barkov A.Y., Sosnovskikh V.Y., Jasińska E. and Jasiński R. (2014) A DFT computational study on the molecular mechanism of the nitro group migration in the product derived from 3-nitro-2-(trifluoromethyl)-2H-chromene and 2-(1-phenylpropylidene)malononitrile. J. Flu. Chem., 168, 236 - 239
2 Nowakowska-Bogdan E., Dresler E. (2012) Optimization of conditions of condensation of phenol with methyl pyruvate in acidic 1-n-butyl-3-methylimidazolium aluminium chloride ionic liquid medium. Przem. Chem., 91, 1931-1934
3 Nowakowska-Bogdan E. and Dresler E. (2013) Condensation of phenols with methylpyruvate in 1-n-butyl-3-methylimidazolium aluminium chloride ionic liquid medium. Przem. Chem., 92, 1868-1871
4 Dresler E., Nowakowska-Bogdan E., Kulesza R., and Jasiński R. (2013) Temperature and solvent effect on the thermodynamic equilibrium in the intramolecular transesterification process of ethyl 4-(4-hydroxyphenyl)-4-(2-hydroxyphenyl)-pentanoate. Przem. Chem., 92, 1876-1878
5 Wang C.H. and Nakamura S. (1995) Synthesis of aromatic polyesters having pendant carboxyl groups in the side chains and conversion of the carboxyl groups to other reactive groups. J. Polym. Sci. Part A Polym. Chem. 33, 2157-2163
6 Rodewald B. and Ritter H. (1999) Oligo(ether sulfones). 3.† Block Copolymers via Condensation Reactions of Telechelic Oligo(ether sulfones) Bearing Phenolic Endgroups and Oligomeric r,ö-Diols. Macromolecules, 32, 1697-1700
7 Gong C. and Fréchet J.M.J., (2000) Proton Transfer Polymerization in the Preparation of Hyperbranched Polyesters with Epoxide Chain-Ends and Internal Hydroxyl Functionalities. Macromolecules, 33, 4997-4999
8 Park D.W., Ha D.H., Park J.Y., Moon J.Y. and Lee H.S. (2001) Synthesis of aromatic polyesters bearing pendant carboxyl groups by phase transfer catalysis. React. Kinet. Catal. Lett., 72, 219-227
9 Zhang R.F. and Moore J.A. (2002) Synthesis, Characterization and Properties of Polycarbonate Containing diphenolic acid. Polym. Prepr., 43, 1007-1008
10 Kim K.H., Moon J.Y., Ha D.H., and Park D.W. (2002) Synthesis of aromatic polyesters using polymeric catalysts having quaternary ammonium salt groups. React. Kinet. Catal. Lett., 75, 385-395
11 Zhang R. F. and Moore J.A. (2003) Synthesis, Characterization and Properties of Polycarbonate Containing Carboxyl Side Groups. Macromol. Symp. 199, 375-390
12 Calò E., Maffezzoli A., Mele G., Martina F., Mazetto S.E., Tarzia A. and Stifani C. (2007) Synthesis of a novel cardanol-based benzoxazine monomer and environmentally sustainable production of polymers and bio-composites. Green Chem., 9, 754-759
13 Zhang P., Wu L., Bu Z. and Li B.G. (2008) Interfacial Polycondensation of Diphenolic Acid and Isophthaloyl Chloride. J. Appl. Polym. Sci., 108, 3586-3592
14 Zhang P., Wu L. and Li B.G. (2009) Thermal stability of aromatic polyesters prepared from diphenolic acid and its esters. Polym. Degrad. Stab., 94, 1261–1266
15 Lochab B., Varma I.K. and Bijwe J. (2010) Thermal behaviour of cardanol-based benzoxazines. Therm. Calorim., 102, 769-774
16 Liu Y., Zhang Y. and Fang Z. (2012) Design, synthesis, and application of novel flame retardants derived from biomass. Bioresour., 7, 4914-4925
17 Zúñiga C., Lligadas G., Ronda J.C., Galià M. and Cádiz V. (2012) Self-foaming diphenolic acid benzoxazine. Polymer, 53 , 3089-3095
18 Hiratsuka Y., Funaya N., Matsunaga H., Haginaka J. (2013) Preparation of magnetic molecularly imprinted polymers for bisphenol A and its analogues and their application to the assay of bisphenol A in river water. J. Pharm. Biomed. Anal., 75, 180-185
19 Peng C., Wu J., Liu J., Qiu L., Liu X., Bo S. and Zhen Z. (2013) Synthesis and optical properties of new fluorinated second-order nonlinear optical copolymers: an attempt toward the balance between solubility and long-term alignment stability. Polym. Chem., 4, 2703-2708
20 Zúñiga C., Larrechi M.S., Lligadas G., Ronda J.C., Galià M. and Cádiz V. (2011) Polybenzoxazines from Renewable Diphenolic Acid. J. Polym. Sci., Part A: Polym. Chem., 49, 1219-1227
21 Zúñiga C., Lligadas G., Ronda J.C., Galià M. and Cádiz V. (2012) Renewable polybenzoxazines based in diphenolic acid. Polymer, 53, 1617-1623
22 Łapczuk-Krygier A., Baranowska K., Ponikiewski L., Matern E., Pikies J. (2012) π-Indenyl substituted zirconium compounds containing terminal bonded phosphanylphosphido ligands. Inorganica Chimica Acta, 387, 361 - 365
23 T. Kolasa et al. (2000) Symmetrical Bis(heteroarylmethoxyphenyl)alkylcarboxylic Acids as Inhibitors of Leukotriene Biosynthesis. J. Med. Chem., 43, 3322-3334
24 Hai-Feng L., Fan-Xin Z., Li D., Bing L., Hao P., Quin-Xiang G. (2013) Brønsted acidic ionic liquids catalyze the high-yield production of diphenolic acid/esters from renewable levulinic acid. Green Chem., 15, 81-84
25 Plechkova N.V and Seddon K.R. (2008) Applications of ionic liquids in the chemical industry. Chem. Soc. Rev., 37 (2008), 123-150
26 Yue C., Fang D., Liu L. and Yi T.F. (2011) Synthesis and application of task-specific ionic liquids used as catalysts and/or solvents in organic unit reactions. J. Mol. Liq., 163, 99–121
27 Khaligh N.G. (2012) Synthesis of coumarins via Pechmann reaction catalyzed by 3-methyl-1-sulfonic acid imidazolium hydrogen sulfate as an efficient, halogen-free and reusable acidic ionic liquid. Catal. Sci. Technol., 2, 1633-1636
28 Shaterian H. R. and Aghakhanizadeh M. (2013) Ionic-liquid-catalyzed green synthesis of coumarin derivatives under solvent-free conditions. Chinese J. Catal., 34, 1690–1696
29 Ghosh P.K., Guha T. and Saha A.N. (1967) Kinetic study of formation of bisphenol a. J. Appl. Chem., 17, 239- 240
30 Pérez P., Domingo L.R., Aizman A. and Contreras R. (2008) The electrophilicity index in organic chemistry. Theor. Aspects Chem. React., 19, 139-201
31 Domingo L.R., Aurell M.J., Perez P. and Contreras R. (2002) Quantitative characterization of the global electrophilicity power of common diene/dienophile pairs in Diels-Alder reactions. Tetrahedron, 58, 4417-4423
32 Chattaraj P.K., Giri S. and Duley S. (2011) Electrophilicity Index. Chem. Rev., 111, PR43-PR75
33 Domingo L.R. (2024) 1999 – 2024, a Quarter Century of the Parr’s Electrophilicity ω Index. Scientiae Radices, 3(3), 156-186
34 Fryźlewicz A., Olszewska A., Zawadzińska K., Woliński P., Kula K., Kącka-Zych A., Łapczuk-Krygier A. and Jasiński R. (2022) On the Mechanism of the Synthesis of Nitrofunctionalised Δ2-Pyrazolines via [3+2] Cycloaddition Reactions between α-EWG-Activated Nitroethenes and Nitrylimine TAC Systems. Organics, 3(1), 59 - 76
35 M.J. Frisch et al. (2009) Gaussian 09 rev A.1 Gaussian, Inc. Wallingford CT
36 Parr R.G. and Yang W. (1989) Density Functional Theory of Atoms and Molecules. Oxford University, New York
37 Sadowski M., Dresler E., Zawadzinska-Wrochniak K., Wroblewska A., and Jasinski R. (2024) Syn-propanethial S-oxide as the natural available building block for the preparation of nitrofunctionalized sulfur containing five-membered heterocycles: MEDT study. Molecules, 29, 4892
38 Łapczuk-Krygier A., Korotaev V.Y., Barkov A.Y., Sosnovskikh V.Y., Jasińska E. and Jasiński R. (2014) A DFT computational study on the molecular mechanism of the nitro group migration in the product derived from 3-nitro-2-(trifluoromethyl)-2H-chromene and 2-(1-phenylpropylidene)malononitrile. J. Flu. Chem., 168, 236 - 239