Synthesis and Structural Features of Hydrogen-Bonded Networks Based on The Combination of Tectons Triphenylboroxine Cation and Pt(SCN)4 Anion Salts

Yıl 2021, , 1980 - 1989, 01.09.2021

Fümet Üstündağ Elif Güngör , Hülya Kara Subasat

https://doi.org/10.21597/jist.857611

Cited By: 1

Öz

In this work, a new compound [C15H16B3N3O5].[Pt(SCN)4].2(H2O] (1) has been synthesized and structurally characterized. The compound (1) crystallizes in monoclinic, space group P21/c a=10.443 Å, b= 24.918 Å, c= 15.048 Å, 𝛼=90, β=133.945, γ=90, V=2819.4 Å3, Z=4. The use of molecular tecton (building block) able to form thiocyano-based hydrogen-bonded synthons (OH···SCN) to synthesize a diverse range of crystal structures is described. In the crystal structure, molecules are linked by intermolecular SCN···HN and BO···HN hydrogen bonds, forming a threedimensional network.

Anahtar Kelimeler

Boroxine compound, single-crystal structure, hydrogen bonds synthons, supramolecular frameworks

Destekleyen Kurum

Balıkesir Üniversitesi

Proje Numarası

BAP-2013/23

Teşekkür

The authors are grateful to the Research Funds of Balikesir University (BAP-2013/23) for the financial support and Prof. Guy Orpen (School of Chemistry, University of Bristol, UK) for his hospitality and the use of the X-ray diffractometer.

Kaynakça

• 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.
• Aakeröy CB and Salmon DJ, 2005. Building Co-crystals with Molecular Sense and Supramolecular Sensibility. CrystEngComm, 7: 439–448.
• Bowmaker GA, Pakawatchai C, Saithong S, Skelton BW and White AH, 2009. 1 : 1 Complexes of Silver(i) thiocyanate with (substituted) Thiourea Ligands. Dalton Transactions, 14: 2588–2598.
• Braga D, Polito M, Bracaccini M, D’Addario D, Tagliavini E, Sturba L and Grepioni F, 2003. Novel Organometallic Building Blocks for Molecular Crystal Engineering. 2. Synthesis and Characterization of Pyridyl and Pyrimidyl Derivatives of Diboronic Acid, [Fe(η5-C5H4-B(OH)2)2], and of Pyridyl Boronic Acid, [Fe(η5-C5H4-4-C5H4N)(η5-C5H4-B(OH)2)].Organometallics, 22: 2142–2150.
• 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.
• Cambre JN and Sumerlin BS, 2011. Biomedical Applications of Boronic Acid Polymers. Polymer, 52: 4631–4643.
• 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.
• Coban MB, Erkarslan U, Oylumluoglu G, Aygun M and Kara H, 2016. Hydrothermal synthesis, crystal structure and Photoluminescent properties; 3D Holmium(III) coordination polymer. Inorganica Chimica Acta, 447: 87–91.
• Dai C, Cheng Y, Cui J and Wang B, 2010. Click Reactions and Boronic Acids: Applications, Issues and Potential Solutions. Molecules, 15: 5768–5781.
• Deplano P, Mercuri ML, Marchiò L, Pilia L, Salidu M, Serpe A and Tronci E, 2004. Salts of Cationic Platinum Dithiolenes with Anionic Platinum Complexes. Structural Characterization of [Pt(Me2pipdt)2][Pt(SCN)4] (Me2pipdt=N,N’-dimethyl-piperazine-2,3-dithione). Inorganica Chimica Acta, 357: 1608–1612.
• 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, Oylumluoglu G, Coban MB, Ozturk E and Kara H, 2016. Cyanide-bridged trinuclear MnIII–FeIII assembly: Crystal structure, magnetic and photoluminescence behavior. Inorganica Chimica Acta, 445: 57–61.
• Erkarslan U, Donmez A, Kara H, Aygun M and Coban MB, 2018. Synthesis, Structure and Photoluminescence Performance of a New Er3+ Cluster-Based 2D Coordination Polymer. Journal of Cluster Science, 29: 1177–1183.
• Hall DG, 2011. Boronic Acids: Preparation and Applications in Organic Synthesis, Medicine and Materials 2 Volume Set, 2nd Completely Revised Edition.
• 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.
• Kara H, Adams CJ, Orpen AG and Podesta TJ, 2006. Pyridinium Boronic Acid Salts in Crystal Synthesis. New Journal of Chemistry, 30: 1461–1469.
• Kara H, Adams CJ, Schwarz B and Orpen AG, 2011. The Use of [Fe(dithiooxalate)2(NO)]2− as a Tecton in Crystal Engineering. CrystEngComm, 13: 5082–5087.
• Kocak C, Oylumluoglu G, Donmez A, Coban MB, Erkarslan U, Aygun M and Kara H, 2017. Crystal structure and photoluminescence properties of a new monomeric copper (II) complex: bis (3-{[(3-hydroxypropyl) imino] methyl}-4-nitrophenolato-κ3O,N,O′) copper (II). Acta Crystallographica Section C: Structural Chemistry, 73: 414–419.
• Korich AL and Iovine PM, 2010. Boroxine Chemistry and Applications: A Perspective. Dalton Transactions, 39: 1423–1431.
• Marinaro WA, Schieber LJ, Munson EJ, Day VW and Stella VJ, 2012. Properties of A Model Aryl Boronic Acid and Its Boroxine. Journal of Pharmaceutical Sciences, 101: 3190–3198.
• Neochoritis CG, Shaabani S, Ahmadianmoghaddam M, Zarganes-Tzitzikas T, Gao L, Novotná M, Mitríková T, Romero AR, Irianti MI, Xu R, Olechno J, Ellson R, Helan V, Kossenjans M, Groves MR and Dömling A, 2019. Rapid Approach to Complex Boronic Acids. Science Advances, 5: 1–9.
• Otgonbaatar E, Chung MC, Umakoshi K and Kwak CH, 2015. Preparation and Luminescent Property of the Self-Assembled Nanoscale Network Systems Combined Tetracyanoplatinate(II) and Copper(II)-Polyaza Complexes. Journal of Nanoscience and Nanotechnology, 15: 1389–1395.
• Pedireddi, VR and SeethaLekshmi N, 2004. Boronic Acids in The Design and Synthesis of Supramolecular Assemblies. Tetrahedron Letters, 45: 1903–1906.
• Rodríguez-Cuamatzi P, Luna-garcía R, Torres-huerta A, Bernal-Uruchurtu, MI, Barba V and Höpfl H, 2009. On the Organizing Role of Water Molecules in the Assembly of Boronic Acids and 4,4′-Bipyridine: 1D, 2D and 3D Hydrogen-Bonded Architectures Containing Cyclophane-Type Motifs. Crystal Growth and Design, 9: 1575–1583.
• Sheldrick GM, 2008. A Short History of SHELX. Acta Crystallographica A64: 112–122.
• 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.
• Tan YS, Sudlow, AL, Molloy KC, Morishima Y, Fujisawa K, Jackson WJ, Henderson W, Halim SNBA, Ng SW and Tiekink ERT, 2013. Supramolecular İsomerism in A Cadmium Bis(N-hydroxyethyl, N-isopropyldithiocarbamate) Compound: Physiochemical Characterization of Ball (n = 2) and Chain (n = ∞) forms of {Cd[S2CN(iPr)CH2CH2OH]2·solvent}n. Crystal Growth and Design, 13: 3046–3056.
• SAINT V7.60A, Bruker-AXS, 2008. Inc. Madison, Wisconsin, USA.
• Whyte GF, Vilar R and Woscholski R, 2013. Molecular Recognition with Boronic Acids-Applications in Chemical Biology. Journal of Chemical Biology, 6: 161–174.
• 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 Reserarch Reviews, 23: 346–368.
• SAINT V7.60A, Bruker-AXS (2008), Inc. Madison, Wisconsin, USA.
• Whyte GF, Vilar R & Woscholski R, (2013). Molecular recognition with boronic acids-applications in chemical biology. Journal of Chemical Biology 6, 161–174.
• Yahsi Y, Gungor E & 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 & Wang B, (2003). Boronic acid compounds as potential pharmaceutical agents. Medicinal Reserarch Reviews 23, 346–368.