Synthesis and crystal structure of new [Pyridine-4-boronic acid methyl ester and Nickel(II) dithiooxalate] compound
Yıl 2022,
, 750 - 756, 08.07.2022
Hülya Kara Subasat
,
Elif Güngör
Öz
In this study, a new compound [HNC5H4B(OH)(OCH3)-4]2[Ni(S2C2O2)2], [Pyridine-4-boronic acid methyl ester and Nickel(II) dithiooxalate] was synthesized and its crystal structure was determined by the single-crystal X-ray diffraction method. The compound crystallized in the monoclinic crystal system in the P21/n space group. The NiII ion is four-coordinated and has a slightly distorted square-plane geometry. There is NH⋯O, OH⋯O and CH⋯O hydrogen bond interactions in the crystal structure. These interactions form a 3-dimension network stacked along the c axis in the ab plane.
Kaynakça
- Fujita, N., Shinkai, S., James, T.D., Boronic Acids in Molecular Self‐Assembly, Chemistry – An Asian Journal, 3, 1076–1091, (2008).
- James, T.D., Self and directed assembly: people and molecules, Beilstein Journal of Organic Chemistry, 12, 391–405, (2016).
- Georgiou, I., Ilyashenko, G., Whiting, A., Synthesis of Aminoboronic Acids and Their Applications in Bifunctional Catalysis, Accounts of Chemical Research, 42, 756–768, (2009).
- Georgiou, I., Kervyn, S., Rossignon, A., De Leo, F., Wouters, J., Bruylants, G., Bonifazi, D., Versatile Self-Adapting Boronic Acids for H-Bond Recognition: From Discrete to Polymeric Supramolecules, Journal of the American Chemical Society, 139, 2710–2727, (2017).
- Silva, M.P., Saraiva, L., Pinto, M., Sousa, M.E., Boronic Acids and Their Derivatives in Medicinal Chemistry: Synthesis and Biological Applications, Molecules, 25, 4323, (2020).
- Trippier, P.C., McGuigan, C., Boronic acids in medicinal chemistry: anticancer, antibacterial and antiviral applications, Medchemcomm, 1, 183, (2010).
- Stubelius, A., Lee, S., Almutairi, A., The Chemistry of Boronic Acids in Nanomaterials for Drug Delivery, Accounts of Chemical Research, 52, 3108–3119, (2019).
- Plescia, J., Moitessier, N., Design and discovery of boronic acid drugs, European Journal of Medicinal Chemistry, 195, 112270, (2020).
- Hatanaka, H., Komada, F., Shiono, M., Mishima, Y., Okumura, K., Tissue Distribution of Para-boronophenylalanine Administered Orally as a Cyclodextrin Inclusion Complex to Melanoma-Bearing Hamsters, Pigment Cell Research, 5, 38–40, (1992).
- Roughley, S.D., Jordan, A.M., The Medicinal Chemist’s Toolbox: An Analysis of Reactions Used in the Pursuit of Drug Candidates, Journal of Medicinal Chemistry, 54, 3451–3479, (2011).
- Marinaro, W.A., Schieber, L.J., Munson, E.J., Day, V.W., Stella, V.J., Properties of a Model Aryl Boronic Acid and Its Boroxine, Journal of Pharmaceutical Sciences, 101, 3190–3198, (2012).
- Karakuş, M.F., Arda, H.N., Ikinciogullari, A., Gedikli, Y., Coşkun, S., Balaban, N., Akdogan, O., Microbiology of the external auditory canal in patients with asteatosis and itching, Kulak Burun Bogaz Ihtisas Dergisi, 11, 33–38, (2003).
- Çetiner, H., Şenol, F.F., Düzer, S., Akut Diffüz Eksternal Otit Tedavisinde Borik Asidin ve Deksametazon- Siprofloksasin Kombinasyonunun İyileşmeye ve Mikrobiyal Flora Üzerine Etkisi, Fırat Tıp Dergisi, 25, 219–223, (2020).
- Torborg, C., Beller, M., Recent Applications of Palladium-Catalyzed Coupling Reactions in the Pharmaceutical, Agrochemical, and Fine Chemical Industries, Advanced Synthesis & Catalysis, 351, 3027–3043, (2009).
- Damera, N.R., Pasam, V.K., Performance profiling of boric acid as lubricant in machining, Journal of the Brazilian Society of Mechanical Sciences, 30 (2008).
- Wang, P., Pei, D., Wang, Z., Li, M., Ma, X., You, J., Li, C., Biocompatible and self-healing ionic gel skin as shape-adaptable and skin-adhering sensor of human motions, Chemical Engineering Journal, 398, 125540, (2020).
- Kicheol, K., Kim, K., Valuable Recycling of waste glass generated from the liquid crystal display panel industry, Journal of Cleaner Production, 174, 191–198, (2018).
- Brooks, W.L.A., Sumerlin, B.S., Synthesis and Applications of Boronic Acid-Containing Polymers: From Materials to Medicine, Chemical Reviews, 116, 1375–1397, (2016).
- Cambre, J.N., Sumerlin, B.S., Biomedical applications of boronic acid polymers, Polymer, 52, 4631–4643, (2011).
- Yang, W., Gao, X., Wang, B., Boronic acid compounds as potential pharmaceutical agents, Medicinal Research Reviews, 23, 346–368, (2003).
- Coban, M.B., Hydrothermal synthesis, crystal structure, luminescent and magnetic properties of a new mononuclear GdIII coordination complex, Journal of Molecular Structure, 1162, 109–116, (2018).
- Yahsi, Y., X-ray characterization and magnetic properties of dioxygen-bridged Cu II and Mn III Schiff base complexes, Acta Crystallographica Section C: Structural Chemistry, 72, 585–592, (2016).
- Kara, H., Adams, C.J., Orpen, A.G., Podesta, T.J., Pyridinium boronic acid salts in crystal synthesis, New Journal of Chemistry, 30, 1461–1469, (2006).
- Yahsi, Y., Gungor, E., Kara, H., Chlorometallate-Pyridinium Boronic Acid Salts for Crystal Engineering: Synthesis of One-, Two-, and Three-Dimensional Hydrogen Bond Networks, Crystal Growth & Design, 15, 2652–2660, (2015).
- U. SAINT V7.60A, Bruker-AXS (2008), Inc. Madison, Wisconsin.
- Dolomanov, O.V., Bourhis, L.J., Gildea, R.J., Howard, J.A.K., Puschmann, H., OLEX2 : a complete structure solution, refinement and analysis program, Journal of Applied Crystallography, 42, 339–341, (2009).
- Sheldrick, G.M., A short history of SHELX, Acta Crystallography, A64, 112–122, (2008).
- Macrae, C.F., Edgington, P.R., McCabe, P., Pidcock, E., Shields, G.P., Taylor, R., Towler, M., van de Streek, J., Mercury : visualization and analysis of crystal structures, Journal of Applied Crystallography, 39, 453–457, (2006).
- Harvey, H.B.J., Gray, P.D.; Low-lying singlet and triplet electronic excited states of binuclear (d10-d10) palladium(0) and platinum(0) complexes, Journal of the American Chemical Society, 110, 2145, (1988).
- Gungor, E., Kara Subasat, H., Synthesis and Crystal Structure of New Compound Containing 4-Pyridine Boronic Acid Cation and [Pd(S2C2O2)2] Anion, Journal of the Institute of Science and Technology, 11, 1921–1927 (2021).
Yeni [Piridin-4-boronik asit metil ester ve Nikel(II) ditiooksalat] bileşiğinin sentezi ve kristal yapısı
Yıl 2022,
, 750 - 756, 08.07.2022
Hülya Kara Subasat
,
Elif Güngör
Öz
Bu çalışmada yeni bir bileşik [HNC5H4B(OH)(OCH3)-4]2[Ni(S2C2O2)2], [Piridin-4-boronik asit metil ester ve Nikel(II) ditiooksalat] sentezlendi ve onun kristal yapısı tek kristal X-ışını difraktometresi metodu ile belirlendi. Bileşik P21/n uzay grubunda monoklinik kristal sisteminde kristallendi. NiII iyonu dört koordinasyonlu ve hafifçe bozulmuş kare düzlem geometriye sahiptir. Kristal yapıda, NH⋯O, OH⋯O ve CH⋯O hidrojen bağ etkileşimleri vardır. Bu etkileşimler ab düzleminde c ekseni boyunca paketlenir ve 3 boyutlu bir ağ oluşturur.
Kaynakça
- Fujita, N., Shinkai, S., James, T.D., Boronic Acids in Molecular Self‐Assembly, Chemistry – An Asian Journal, 3, 1076–1091, (2008).
- James, T.D., Self and directed assembly: people and molecules, Beilstein Journal of Organic Chemistry, 12, 391–405, (2016).
- Georgiou, I., Ilyashenko, G., Whiting, A., Synthesis of Aminoboronic Acids and Their Applications in Bifunctional Catalysis, Accounts of Chemical Research, 42, 756–768, (2009).
- Georgiou, I., Kervyn, S., Rossignon, A., De Leo, F., Wouters, J., Bruylants, G., Bonifazi, D., Versatile Self-Adapting Boronic Acids for H-Bond Recognition: From Discrete to Polymeric Supramolecules, Journal of the American Chemical Society, 139, 2710–2727, (2017).
- Silva, M.P., Saraiva, L., Pinto, M., Sousa, M.E., Boronic Acids and Their Derivatives in Medicinal Chemistry: Synthesis and Biological Applications, Molecules, 25, 4323, (2020).
- Trippier, P.C., McGuigan, C., Boronic acids in medicinal chemistry: anticancer, antibacterial and antiviral applications, Medchemcomm, 1, 183, (2010).
- Stubelius, A., Lee, S., Almutairi, A., The Chemistry of Boronic Acids in Nanomaterials for Drug Delivery, Accounts of Chemical Research, 52, 3108–3119, (2019).
- Plescia, J., Moitessier, N., Design and discovery of boronic acid drugs, European Journal of Medicinal Chemistry, 195, 112270, (2020).
- Hatanaka, H., Komada, F., Shiono, M., Mishima, Y., Okumura, K., Tissue Distribution of Para-boronophenylalanine Administered Orally as a Cyclodextrin Inclusion Complex to Melanoma-Bearing Hamsters, Pigment Cell Research, 5, 38–40, (1992).
- Roughley, S.D., Jordan, A.M., The Medicinal Chemist’s Toolbox: An Analysis of Reactions Used in the Pursuit of Drug Candidates, Journal of Medicinal Chemistry, 54, 3451–3479, (2011).
- Marinaro, W.A., Schieber, L.J., Munson, E.J., Day, V.W., Stella, V.J., Properties of a Model Aryl Boronic Acid and Its Boroxine, Journal of Pharmaceutical Sciences, 101, 3190–3198, (2012).
- Karakuş, M.F., Arda, H.N., Ikinciogullari, A., Gedikli, Y., Coşkun, S., Balaban, N., Akdogan, O., Microbiology of the external auditory canal in patients with asteatosis and itching, Kulak Burun Bogaz Ihtisas Dergisi, 11, 33–38, (2003).
- Çetiner, H., Şenol, F.F., Düzer, S., Akut Diffüz Eksternal Otit Tedavisinde Borik Asidin ve Deksametazon- Siprofloksasin Kombinasyonunun İyileşmeye ve Mikrobiyal Flora Üzerine Etkisi, Fırat Tıp Dergisi, 25, 219–223, (2020).
- Torborg, C., Beller, M., Recent Applications of Palladium-Catalyzed Coupling Reactions in the Pharmaceutical, Agrochemical, and Fine Chemical Industries, Advanced Synthesis & Catalysis, 351, 3027–3043, (2009).
- Damera, N.R., Pasam, V.K., Performance profiling of boric acid as lubricant in machining, Journal of the Brazilian Society of Mechanical Sciences, 30 (2008).
- Wang, P., Pei, D., Wang, Z., Li, M., Ma, X., You, J., Li, C., Biocompatible and self-healing ionic gel skin as shape-adaptable and skin-adhering sensor of human motions, Chemical Engineering Journal, 398, 125540, (2020).
- Kicheol, K., Kim, K., Valuable Recycling of waste glass generated from the liquid crystal display panel industry, Journal of Cleaner Production, 174, 191–198, (2018).
- Brooks, W.L.A., Sumerlin, B.S., Synthesis and Applications of Boronic Acid-Containing Polymers: From Materials to Medicine, Chemical Reviews, 116, 1375–1397, (2016).
- Cambre, J.N., Sumerlin, B.S., Biomedical applications of boronic acid polymers, Polymer, 52, 4631–4643, (2011).
- Yang, W., Gao, X., Wang, B., Boronic acid compounds as potential pharmaceutical agents, Medicinal Research Reviews, 23, 346–368, (2003).
- Coban, M.B., Hydrothermal synthesis, crystal structure, luminescent and magnetic properties of a new mononuclear GdIII coordination complex, Journal of Molecular Structure, 1162, 109–116, (2018).
- Yahsi, Y., X-ray characterization and magnetic properties of dioxygen-bridged Cu II and Mn III Schiff base complexes, Acta Crystallographica Section C: Structural Chemistry, 72, 585–592, (2016).
- Kara, H., Adams, C.J., Orpen, A.G., Podesta, T.J., Pyridinium boronic acid salts in crystal synthesis, New Journal of Chemistry, 30, 1461–1469, (2006).
- Yahsi, Y., Gungor, E., Kara, H., Chlorometallate-Pyridinium Boronic Acid Salts for Crystal Engineering: Synthesis of One-, Two-, and Three-Dimensional Hydrogen Bond Networks, Crystal Growth & Design, 15, 2652–2660, (2015).
- U. SAINT V7.60A, Bruker-AXS (2008), Inc. Madison, Wisconsin.
- Dolomanov, O.V., Bourhis, L.J., Gildea, R.J., Howard, J.A.K., Puschmann, H., OLEX2 : a complete structure solution, refinement and analysis program, Journal of Applied Crystallography, 42, 339–341, (2009).
- Sheldrick, G.M., A short history of SHELX, Acta Crystallography, A64, 112–122, (2008).
- Macrae, C.F., Edgington, P.R., McCabe, P., Pidcock, E., Shields, G.P., Taylor, R., Towler, M., van de Streek, J., Mercury : visualization and analysis of crystal structures, Journal of Applied Crystallography, 39, 453–457, (2006).
- Harvey, H.B.J., Gray, P.D.; Low-lying singlet and triplet electronic excited states of binuclear (d10-d10) palladium(0) and platinum(0) complexes, Journal of the American Chemical Society, 110, 2145, (1988).
- Gungor, E., Kara Subasat, H., Synthesis and Crystal Structure of New Compound Containing 4-Pyridine Boronic Acid Cation and [Pd(S2C2O2)2] Anion, Journal of the Institute of Science and Technology, 11, 1921–1927 (2021).