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Synthesis, Crystal Structure and Hydrogen Bond Properties of {[HNC5H4B(OH)(OCH3)- 4]2PdCl2} New Compound

Year 2022, Volume: 12 Issue: 3, 1489 - 1495, 01.09.2022
https://doi.org/10.21597/jist.1075695

Abstract

In this study, the new compound {[HNC5H4B(OH)(OCH3)-4]2PdCl2} was synthesized
and its crystal structure was determined. Compound crystallized in the space group P21/n in the
monoclinic crystal system at a=3.8749 (8) Å, b=10.177 (2) Å, c=20.403 (4) Å, α= γ = 90°, β =91.78°
and Z=2 units cell parameters The Pd ion in the compound is at the inversion center and has a quaternary
coordination. Because the N–Pd–N* and Cl–Pd–Cl* angles are 180°, the Pd ion has a square plane
geometry. The CH···O, CH···Cl and π···π interactions in the compound form a 3-dimensional
structure in the bc plane and along a axis.

References

  • Aakeröy CB, Desper J and Levin B, 2005. Crystal Engineering Gone Awry and The Emergence of The Boronic Acid–Carboxylate Synthon. CrystEngComm, 7:102–107.
  • Acıkbas G, Calıs Acıkbas N, 2022. The Effect of Sintering Regime on Superhydrophobicity of Silicon Nitride Modified Ceramic Surfaces. Journal of Asian Ceramic Societies, 734-744.
  • Brdar-Jokanović M, 2020. Boron Toxicity and Deficiency in Agricultural Plants. International Journal of Molecular Science, 21(4):1424.
  • Brooks WLA and Sumerlin BS, 2016. Synthesis and Applications of Boronic Acid-Containing Polymers: From Materials to Medicine. Chemical Reviews, 116:1375–1397.
  • Cai D, Larsen, RD and Reider PJ, 2002. Effective Lithiation of 3-Bromopyridine: Synthesis of 3-Pyridine Boronic Acid and Variously 3-Substituted Pyridines. Tetrahedron Letters, 43:4285–4287.
  • Campos-Gaxiola JJ, García-Grajeda BA, Hernández-Ahuactzi IF, Guerrero-Álvarez JA, Höpfl H and Cruz-Enríquez A, 2017. Supramolecular Networks in Molecular Complexes of Pyridine Boronic Acids and Polycarboxylic Acids: Synthesis, Structural Characterization and Fluorescence Properties. CrystEngComm, 19:3760–3775.
  • Çetiner H, Şenol FF, Düzer S, 2020. Klinik Araştırma Akut Diffüz Eksternal Otit Tedavisinde Borik Asidin ve Deksametazon- Siprofloksasin Kombinasyonunun İyileşmeye ve Mikrobiyal Flora Üzerine Etkisi. Fırat Tıp Dergisi, 25:219–223.
  • Cui X, Wang Y, Yan Y, Meng Z, Lu R, Gao H, Pan C, Wei X, Zhou W, 2022. Phenylboronic Acid-Functionalized Cross-Linked Chitosanmagnetic Adsorbents for The Magnetic Solid-Phaseextraction of Benzoylurea Pesticides. Journal of Separation Science 45:908–918.
  • Damera NR and Pasam VK, 2008. Performance Profiling of Boric acid as Lubricant in Machining. Journal of the Brazilian Society of Mechanical Sciences and Engineering, 3:239-244.
  • Dolomanov OV, Bourhis LJ, Gildea RJ, Howard, JAK and Puschmann H, 2009. OLEX2: A Complete Structure Solution, Refinement and Analysis Program. Journal of Applied Crystallography, 42:339–341. Erkarslan U, Dönmez A, Kara Subaşat H, Aygün M, Çoban MB, 2018. Synthesis, Structure and Photoluminescence Performance of a New Er3-Cluster-Based 2D Coordination Polymer. Journal of Cluster Science, 29: 1177-1183.
  • Fujita N, Shinkai S and James TD, 2008. Boronic Acids in Molecular Self‐Assembly. Chemistry An Asian Journal, 3:1076–1091.
  • Gungor E, 2017. 3-D Polymeric Structure Formed by Hydrogen Bonds of Copper (II) Complex. Molecular Crystals and Liquid Crystals, 642:21–28.
  • Habes D, Morakchi S, Aribi N, Farine JP and Soltani N, 2006. Boric Acid Toxicity to The German Cockroach, Blattella Germanica: Alterations in Midgut Structure, And Acetylcholinesterase and Glutathione S-Transferase Activity. Pesticide Biochemistry and Physiology, 84:17–24.
  • Hall DG, 2011. In Boronic Acids: Preparation and Applications in Organic Synthesis, Medicine and Materials Second Edition, Wiley-VCH Verlag GmbH and Co. KGaA, Weinheim, Germany.
  • Hernández MF, López PV, Conconi MS and Rendtorff NM, 2022. Effect of Boron Sources in The Thermal Behavior of A Clay-Based Ceramics. Open Ceramics, 100227.
  • Hernández MF, Violini MA, Serra MF, Conconi MS, Suarez G and Rendtorff NM, 2020. Boric Acid (H3BO3) as Flux Agent of Clay-Based Ceramics, B2O3 Effect in Clay Thermal Behavior and Resultant Ceramics Properties. Journal of Thermal Analysis and Calorimetry, 139:1717–1729.
  • Hezil H, 2016. Preparation, Structural and Thermal Studies of Boroxine Adducts Having Aryl Boronic Acids and Pyrazoles. African Journal of Pure and Applied Chemistry, 10:42–55.
  • James TD, 2016. Self and Directed Assembly: People and Molecules. Beilstein Journal of Organic Chemistry, 12:391–405.
  • Kadam RN, Shendge RS and Pande VV, 2015. A Review of Nanotechnology with an Emphasis on Nanoplex. Brazilian Journal of Pharmaceutical Sciences, 51:255–263. Karakuş MF, Arda HN, Ikinciogullari A, Gedikli Y, Coşkun S, Balaban N and Akdogan O, 2003. Asteatosis ve Kaşıntılı Hastalarda Dış Kulak Yolu Mikrobiyolojisi. Kulak Burun Bogaz İhtisas Dergisi, 11:33–38.
  • Kim K and Kim K, 2018. Valuable Recycling of Waste Glass Generated from The Liquid Crystal Display Panel İndustry. Journal of Cleaner Production 174:191–198.
  • Kinzhalov MA, Novikov AS, Chernyshev AN and Suslonov VV, 2017. Intermolecular Hydrogen Bonding H···Cl− in The Solid Palladium(II)-Diaminocarbene Complexes. Zeitschrift für Kristallographie - Crystalline Materials, 232:299–305.
  • Li B, Li T, Aliyu MA, Li ZH, Tang W, 2019. Enantioselective Palladium‐Catalyzed Cross‐Coupling of α‐Bromo Carboxamides and Aryl Boronic Acids. Angewandte Chemie, 201905174.
  • Macrae CF, Edgington PR, McCabe P, Pidcock E, Shields GP, Taylor R, Towler M and van de Streek J, 2006. Mercury: Visualization and Analysis of Crystal Structures. Journal of Applied Crystallography, 39:453–457.
  • Marinaro WA, Schieber LJ, Munson EJ, Day VW and Stella VJ, 2012. Properties of A Model Aryl Boronic Acid and İts Boroxine. Journal of Pharmaceutical Sciences, 101:3190–3198.
  • Muz B, Azab AK, Confalonieri L, Grosso ED, Fallarini S, Imperio D, Panza L, 2022. Synthesis, Equilibrium, and Biological Study of a C-7 Glucose Boronic Acid Derivative as a Potential Candidate for Boron Neutron Capture Therapy. Bioorganic Medicinal Chemistry, 59:116659.
  • Rihan M, Nalla LV, Dharavath A, Patel S, Shard A, Khairnar A, 2022. Boronic Acid Derivative Activates Pyruvate Kinase M2 İndispensable for Redox Metabolism in Oral Cancer Cells. Bioorganic Medicinal Chemistry Letter, 59:128539.
  • Nobrega G, Rodrigues de Souza R, Gonçalves IM, Moita AS , Ribeiro JE, Lima RA, 2022. Recent Developments on the Thermal Properties, Stability and Applications of Nanofluids in Machining, Solar Energy and Biomedicine. Applied Sciences, 12:1115-1133.
  • Obuobi S, Voo ZX, Low MW, Czarny B, Selvarajan V, Ibrahim NL, Yang YY and Ee PLR, 2018. Phenylboronic Acid Functionalized Polycarbonate Hydrogels for Controlled Release of Polymyxin B in Pseudomonas Aeruginosa Infected Burn Wounds. Advanced Healthcare Materials, 7:1701388.
  • Sen S , Mondal N , Ghosh W and Chakraborty R, 2022. Inducible Boron Resistance Via Active Efflux in Lysinibacillus And Enterococcus İsolates From Boron-Contaminated Agricultural Soil. BioMetals, 35:215–228.
  • Sheldrick GM, 2015. Crystal Structure Refinement with SHELXL. Acta Crystallographica Section C Structural Chemistry, 71:3–8.
  • Sheldrick GM, SADABS V2008/1, University of Göttingen, Germany.
  • Sierras A, Wada-Katsumata A and Schal C, 2018. Effectiveness of Boric Acid by Ingestion, But Not by Contact, Against the Common Bed Bug (Hemiptera: Cimicidae). Journal of Economic Entomology, 111:2772–2781.
  • SAINT V7.60A, Bruker-AXS, 2008. Inc. Madison, Wisconsin, USA.
  • Torborg C and Beller M, 2009. Recent Applications of Palladium‐Catalyzed Coupling Reactions in the Pharmaceutical, Agrochemical, and Fine Chemical Industries. Advanced Synthesis and Catalysis, 351:3027–3043.
  • Tsuchido Y, Horiuchi R, Hashimoto T, Ishihara K, Kanzawa N and Hayashita T, 2019. Rapid and Selective Discrimination of Gram-Positive and Gram-Negative Bacteria by Boronic Acid-Modified Poly(amidoamine) Dendrimer. Analytical Chemistry, 91:3929–3935.
  • Wang P, Pei D, Wang Z, Li M, Ma X, You J and Li C, 2020. Biocompatible and Self-Healing İonic Gel Skin as Shape-Adaptable and Skin-Adhering Sensor of Human Motions. Chemical Engineering Journal, 398: 125540.
  • Yahsi Y, Gungor E and Kara H, 2015. Chlorometallate-Pyridinium Boronic Acid Salts for Crystal Engineering: Synthesis of 1D, 2D and 3D Hydrogen Bond Networks. Crystal Growth and Design, 15: 2652–2660.
  • Yang W, Gao X and Wang B, 2003. Boronic Acid Compounds as Potential Pharmaceutical Agents. Medicinal Research Reviews, 23:346–368.
  • Zhu Q, Saeed M, Song R, Sun T, Jiang C, Yu H, 2020. Dynamic Covalent Chemistry-Regulated Stimuli-Activatable Drug Delivery Systems for Improved Cancer Therapy. Chinese Chemical Letter, 31:1051–1059.
  • Zhu Y, Zeng S, Li B, McEllin AJ, Liao J, Fang Z, Xiao C, Bruce DW, Zhu W, Wang Y, 2022. Liquid-Crystalline Thermally Activated Delayed Fluorescence: Design, Synthesis, and Application in Solution-Processed Organic Light-Emitting Diodes. Applied Materials Interfaces, 14:15437−15447.

{[HNC5H4B(OH)(OCH3)-4]2PdCl2} Yeni Bileşiğin Sentezi, Kristal Yapısı ve Hidrojen Bağ Özellikleri

Year 2022, Volume: 12 Issue: 3, 1489 - 1495, 01.09.2022
https://doi.org/10.21597/jist.1075695

Abstract

Bu çalışmada, yeni bileşik {[HNC5H4B(OH)(OCH3)-4]2PdCl2} sentezlendi ve kristal yapısı
belirlendi. Bileşik, monoklinik kristal sisteminde P21/n uzay grubunda a=3.8749 (8) Å, b=10.177 (2) Å,
c=20.403 (4) Å, α= γ = 90°, β =91.78° ve Z=2 birim hücre parametrelerinde kristallendi. Bileşikteki Pd
iyonu inversiyon merkezinde ve dörtlü bir koordinasyona sahiptir. N–Pd–N* ve Cl–Pd–Cl* açıları 180°
olduğu için, Pd iyonu kare düzlem geometriye sahiptir. Bileşikteki CH···O, CH···Cl ve π···π
etkileşimleri, bc düzleminde ve a ekseni boyunca 3 boyutlu bir yapı oluşturmaktadır.

References

  • Aakeröy CB, Desper J and Levin B, 2005. Crystal Engineering Gone Awry and The Emergence of The Boronic Acid–Carboxylate Synthon. CrystEngComm, 7:102–107.
  • Acıkbas G, Calıs Acıkbas N, 2022. The Effect of Sintering Regime on Superhydrophobicity of Silicon Nitride Modified Ceramic Surfaces. Journal of Asian Ceramic Societies, 734-744.
  • Brdar-Jokanović M, 2020. Boron Toxicity and Deficiency in Agricultural Plants. International Journal of Molecular Science, 21(4):1424.
  • Brooks WLA and Sumerlin BS, 2016. Synthesis and Applications of Boronic Acid-Containing Polymers: From Materials to Medicine. Chemical Reviews, 116:1375–1397.
  • Cai D, Larsen, RD and Reider PJ, 2002. Effective Lithiation of 3-Bromopyridine: Synthesis of 3-Pyridine Boronic Acid and Variously 3-Substituted Pyridines. Tetrahedron Letters, 43:4285–4287.
  • Campos-Gaxiola JJ, García-Grajeda BA, Hernández-Ahuactzi IF, Guerrero-Álvarez JA, Höpfl H and Cruz-Enríquez A, 2017. Supramolecular Networks in Molecular Complexes of Pyridine Boronic Acids and Polycarboxylic Acids: Synthesis, Structural Characterization and Fluorescence Properties. CrystEngComm, 19:3760–3775.
  • Çetiner H, Şenol FF, Düzer S, 2020. Klinik Araştırma Akut Diffüz Eksternal Otit Tedavisinde Borik Asidin ve Deksametazon- Siprofloksasin Kombinasyonunun İyileşmeye ve Mikrobiyal Flora Üzerine Etkisi. Fırat Tıp Dergisi, 25:219–223.
  • Cui X, Wang Y, Yan Y, Meng Z, Lu R, Gao H, Pan C, Wei X, Zhou W, 2022. Phenylboronic Acid-Functionalized Cross-Linked Chitosanmagnetic Adsorbents for The Magnetic Solid-Phaseextraction of Benzoylurea Pesticides. Journal of Separation Science 45:908–918.
  • Damera NR and Pasam VK, 2008. Performance Profiling of Boric acid as Lubricant in Machining. Journal of the Brazilian Society of Mechanical Sciences and Engineering, 3:239-244.
  • Dolomanov OV, Bourhis LJ, Gildea RJ, Howard, JAK and Puschmann H, 2009. OLEX2: A Complete Structure Solution, Refinement and Analysis Program. Journal of Applied Crystallography, 42:339–341. Erkarslan U, Dönmez A, Kara Subaşat H, Aygün M, Çoban MB, 2018. Synthesis, Structure and Photoluminescence Performance of a New Er3-Cluster-Based 2D Coordination Polymer. Journal of Cluster Science, 29: 1177-1183.
  • Fujita N, Shinkai S and James TD, 2008. Boronic Acids in Molecular Self‐Assembly. Chemistry An Asian Journal, 3:1076–1091.
  • Gungor E, 2017. 3-D Polymeric Structure Formed by Hydrogen Bonds of Copper (II) Complex. Molecular Crystals and Liquid Crystals, 642:21–28.
  • Habes D, Morakchi S, Aribi N, Farine JP and Soltani N, 2006. Boric Acid Toxicity to The German Cockroach, Blattella Germanica: Alterations in Midgut Structure, And Acetylcholinesterase and Glutathione S-Transferase Activity. Pesticide Biochemistry and Physiology, 84:17–24.
  • Hall DG, 2011. In Boronic Acids: Preparation and Applications in Organic Synthesis, Medicine and Materials Second Edition, Wiley-VCH Verlag GmbH and Co. KGaA, Weinheim, Germany.
  • Hernández MF, López PV, Conconi MS and Rendtorff NM, 2022. Effect of Boron Sources in The Thermal Behavior of A Clay-Based Ceramics. Open Ceramics, 100227.
  • Hernández MF, Violini MA, Serra MF, Conconi MS, Suarez G and Rendtorff NM, 2020. Boric Acid (H3BO3) as Flux Agent of Clay-Based Ceramics, B2O3 Effect in Clay Thermal Behavior and Resultant Ceramics Properties. Journal of Thermal Analysis and Calorimetry, 139:1717–1729.
  • Hezil H, 2016. Preparation, Structural and Thermal Studies of Boroxine Adducts Having Aryl Boronic Acids and Pyrazoles. African Journal of Pure and Applied Chemistry, 10:42–55.
  • James TD, 2016. Self and Directed Assembly: People and Molecules. Beilstein Journal of Organic Chemistry, 12:391–405.
  • Kadam RN, Shendge RS and Pande VV, 2015. A Review of Nanotechnology with an Emphasis on Nanoplex. Brazilian Journal of Pharmaceutical Sciences, 51:255–263. Karakuş MF, Arda HN, Ikinciogullari A, Gedikli Y, Coşkun S, Balaban N and Akdogan O, 2003. Asteatosis ve Kaşıntılı Hastalarda Dış Kulak Yolu Mikrobiyolojisi. Kulak Burun Bogaz İhtisas Dergisi, 11:33–38.
  • Kim K and Kim K, 2018. Valuable Recycling of Waste Glass Generated from The Liquid Crystal Display Panel İndustry. Journal of Cleaner Production 174:191–198.
  • Kinzhalov MA, Novikov AS, Chernyshev AN and Suslonov VV, 2017. Intermolecular Hydrogen Bonding H···Cl− in The Solid Palladium(II)-Diaminocarbene Complexes. Zeitschrift für Kristallographie - Crystalline Materials, 232:299–305.
  • Li B, Li T, Aliyu MA, Li ZH, Tang W, 2019. Enantioselective Palladium‐Catalyzed Cross‐Coupling of α‐Bromo Carboxamides and Aryl Boronic Acids. Angewandte Chemie, 201905174.
  • Macrae CF, Edgington PR, McCabe P, Pidcock E, Shields GP, Taylor R, Towler M and van de Streek J, 2006. Mercury: Visualization and Analysis of Crystal Structures. Journal of Applied Crystallography, 39:453–457.
  • Marinaro WA, Schieber LJ, Munson EJ, Day VW and Stella VJ, 2012. Properties of A Model Aryl Boronic Acid and İts Boroxine. Journal of Pharmaceutical Sciences, 101:3190–3198.
  • Muz B, Azab AK, Confalonieri L, Grosso ED, Fallarini S, Imperio D, Panza L, 2022. Synthesis, Equilibrium, and Biological Study of a C-7 Glucose Boronic Acid Derivative as a Potential Candidate for Boron Neutron Capture Therapy. Bioorganic Medicinal Chemistry, 59:116659.
  • Rihan M, Nalla LV, Dharavath A, Patel S, Shard A, Khairnar A, 2022. Boronic Acid Derivative Activates Pyruvate Kinase M2 İndispensable for Redox Metabolism in Oral Cancer Cells. Bioorganic Medicinal Chemistry Letter, 59:128539.
  • Nobrega G, Rodrigues de Souza R, Gonçalves IM, Moita AS , Ribeiro JE, Lima RA, 2022. Recent Developments on the Thermal Properties, Stability and Applications of Nanofluids in Machining, Solar Energy and Biomedicine. Applied Sciences, 12:1115-1133.
  • Obuobi S, Voo ZX, Low MW, Czarny B, Selvarajan V, Ibrahim NL, Yang YY and Ee PLR, 2018. Phenylboronic Acid Functionalized Polycarbonate Hydrogels for Controlled Release of Polymyxin B in Pseudomonas Aeruginosa Infected Burn Wounds. Advanced Healthcare Materials, 7:1701388.
  • Sen S , Mondal N , Ghosh W and Chakraborty R, 2022. Inducible Boron Resistance Via Active Efflux in Lysinibacillus And Enterococcus İsolates From Boron-Contaminated Agricultural Soil. BioMetals, 35:215–228.
  • Sheldrick GM, 2015. Crystal Structure Refinement with SHELXL. Acta Crystallographica Section C Structural Chemistry, 71:3–8.
  • Sheldrick GM, SADABS V2008/1, University of Göttingen, Germany.
  • Sierras A, Wada-Katsumata A and Schal C, 2018. Effectiveness of Boric Acid by Ingestion, But Not by Contact, Against the Common Bed Bug (Hemiptera: Cimicidae). Journal of Economic Entomology, 111:2772–2781.
  • SAINT V7.60A, Bruker-AXS, 2008. Inc. Madison, Wisconsin, USA.
  • Torborg C and Beller M, 2009. Recent Applications of Palladium‐Catalyzed Coupling Reactions in the Pharmaceutical, Agrochemical, and Fine Chemical Industries. Advanced Synthesis and Catalysis, 351:3027–3043.
  • Tsuchido Y, Horiuchi R, Hashimoto T, Ishihara K, Kanzawa N and Hayashita T, 2019. Rapid and Selective Discrimination of Gram-Positive and Gram-Negative Bacteria by Boronic Acid-Modified Poly(amidoamine) Dendrimer. Analytical Chemistry, 91:3929–3935.
  • Wang P, Pei D, Wang Z, Li M, Ma X, You J and Li C, 2020. Biocompatible and Self-Healing İonic Gel Skin as Shape-Adaptable and Skin-Adhering Sensor of Human Motions. Chemical Engineering Journal, 398: 125540.
  • Yahsi Y, Gungor E and Kara H, 2015. Chlorometallate-Pyridinium Boronic Acid Salts for Crystal Engineering: Synthesis of 1D, 2D and 3D Hydrogen Bond Networks. Crystal Growth and Design, 15: 2652–2660.
  • Yang W, Gao X and Wang B, 2003. Boronic Acid Compounds as Potential Pharmaceutical Agents. Medicinal Research Reviews, 23:346–368.
  • Zhu Q, Saeed M, Song R, Sun T, Jiang C, Yu H, 2020. Dynamic Covalent Chemistry-Regulated Stimuli-Activatable Drug Delivery Systems for Improved Cancer Therapy. Chinese Chemical Letter, 31:1051–1059.
  • Zhu Y, Zeng S, Li B, McEllin AJ, Liao J, Fang Z, Xiao C, Bruce DW, Zhu W, Wang Y, 2022. Liquid-Crystalline Thermally Activated Delayed Fluorescence: Design, Synthesis, and Application in Solution-Processed Organic Light-Emitting Diodes. Applied Materials Interfaces, 14:15437−15447.
There are 40 citations in total.

Details

Primary Language Turkish
Subjects Metrology, Applied and Industrial Physics
Journal Section Fizik / Physics
Authors

Elif Güngör 0000-0002-7158-9604

Hülya Kara Subasat 0000-0002-2032-8930

Early Pub Date August 26, 2022
Publication Date September 1, 2022
Submission Date February 18, 2022
Acceptance Date August 1, 2022
Published in Issue Year 2022 Volume: 12 Issue: 3

Cite

APA Güngör, E., & Kara Subasat, H. (2022). {[HNC5H4B(OH)(OCH3)-4]2PdCl2} Yeni Bileşiğin Sentezi, Kristal Yapısı ve Hidrojen Bağ Özellikleri. Journal of the Institute of Science and Technology, 12(3), 1489-1495. https://doi.org/10.21597/jist.1075695
AMA Güngör E, Kara Subasat H. {[HNC5H4B(OH)(OCH3)-4]2PdCl2} Yeni Bileşiğin Sentezi, Kristal Yapısı ve Hidrojen Bağ Özellikleri. J. Inst. Sci. and Tech. September 2022;12(3):1489-1495. doi:10.21597/jist.1075695
Chicago Güngör, Elif, and Hülya Kara Subasat. “{[HNC5H4B(OH)(OCH3)-4]2PdCl2} Yeni Bileşiğin Sentezi, Kristal Yapısı Ve Hidrojen Bağ Özellikleri”. Journal of the Institute of Science and Technology 12, no. 3 (September 2022): 1489-95. https://doi.org/10.21597/jist.1075695.
EndNote Güngör E, Kara Subasat H (September 1, 2022) {[HNC5H4B(OH)(OCH3)-4]2PdCl2} Yeni Bileşiğin Sentezi, Kristal Yapısı ve Hidrojen Bağ Özellikleri. Journal of the Institute of Science and Technology 12 3 1489–1495.
IEEE E. Güngör and H. Kara Subasat, “{[HNC5H4B(OH)(OCH3)-4]2PdCl2} Yeni Bileşiğin Sentezi, Kristal Yapısı ve Hidrojen Bağ Özellikleri”, J. Inst. Sci. and Tech., vol. 12, no. 3, pp. 1489–1495, 2022, doi: 10.21597/jist.1075695.
ISNAD Güngör, Elif - Kara Subasat, Hülya. “{[HNC5H4B(OH)(OCH3)-4]2PdCl2} Yeni Bileşiğin Sentezi, Kristal Yapısı Ve Hidrojen Bağ Özellikleri”. Journal of the Institute of Science and Technology 12/3 (September 2022), 1489-1495. https://doi.org/10.21597/jist.1075695.
JAMA Güngör E, Kara Subasat H. {[HNC5H4B(OH)(OCH3)-4]2PdCl2} Yeni Bileşiğin Sentezi, Kristal Yapısı ve Hidrojen Bağ Özellikleri. J. Inst. Sci. and Tech. 2022;12:1489–1495.
MLA Güngör, Elif and Hülya Kara Subasat. “{[HNC5H4B(OH)(OCH3)-4]2PdCl2} Yeni Bileşiğin Sentezi, Kristal Yapısı Ve Hidrojen Bağ Özellikleri”. Journal of the Institute of Science and Technology, vol. 12, no. 3, 2022, pp. 1489-95, doi:10.21597/jist.1075695.
Vancouver Güngör E, Kara Subasat H. {[HNC5H4B(OH)(OCH3)-4]2PdCl2} Yeni Bileşiğin Sentezi, Kristal Yapısı ve Hidrojen Bağ Özellikleri. J. Inst. Sci. and Tech. 2022;12(3):1489-95.