SYNTHESIS, CHARACTERIZATION OF CYANIDE COMPLEXES WITH 2-(HYDROXYMETHYL)PYRIDINE BY VIBRATIONAL SPECTROSCOPIC, THERMAL STUDIES AND ELECTRICAL PROPERTIES
Year 2023,
Volume: 24 Issue: 4 - Eskişehir Technical University Journal of Science and Technology A - Applied Sciences and Engineering, 216 - 229, 27.12.2023
Elvan Sayın
,
Güneş Süheyla Kürkçüoğlu
Abstract
In this investigation, we present synthesis and characterized of three new heteropolynuclear cyanide complexes with 2-(Hydroxymethyl)pyridine (hmpH) of [M(H2O)(hmpH)Ni(CN)4]2·nH2O, (M(II) = Fe, Co and Ni); n = 12 for Fe, 2 for Co and Ni). The obtained complexes have been studied by elemental, thermal analysis, FT-IR, and Raman spectroscopic measurement techniques. Considering the alterations in characteristic peaks of cyanide, aqua, and hmpH ligands, general knowledge about the structural features of the complexes was detected from the vibrational spectra. The Ni(II) ion is coordinated by four cyanide-carbon atoms forming a square planar geometry. In addition, thermal analyses and electrical features of the complexes were investigated.
Supporting Institution
The Research Fund of Eskişehir Osmangazi University.
Thanks
This paper is dedicated to Prof. Dr. Ziya KANTARCI, who died on January, 2012.
References
- [1] Batten SR, Neville SM, Turner DR. Coordination polymers: design, analysis and application. Royal Society of Chemistry, 2009.
- [2] Tadokoro M, Yasuzukara S, Nakamura M, Shinoda T, Tatenuma T, Mitsumi M, Ozawa Y, Toriumi K, Yoshino H, Shiomi D, Sato K, Takui T, Mori T, Murata K. A High Conductivity Crystal Containing a Copper(I) Coordination Polymer Bridged by the Organic Acceptor TANC. Angew Chem 2006; 118: 5268-5271.
- [3] Gapud AA, Weber AP, Alexandera JA, Pham L, Khan A, Leatherbury RI, Reyes AP, Lumata LL, Kuhns PL, Valente EJ, Sykora RE. New quasi-one-dimensional tetracyanidoplatinate, Cs4[Pt(CN)4](CF3SO3)2: Synthesis, structure, and physical characterization. J Phys Chem Solids 2014; 75: 447-452.
- [4] Janiak C. Engineering coordination polymers towards applications. Dalton Trans 2003; 14: 2781-2804.
- [5] Di Noto V, Vittadello M, Greenbaum SG, Suares S, Kano K, Furukawa T. A new class of lithium hybrid gel electrolyte systems. J Phys Chem B 2004; 108: 18832-18844.
- [6] Real JA, Gaspar AB, Munoz MC. Thermal, pressure and light switchable spin-crossover materials. Dalton Trans 2005; 12: 2062-2079.
- [7] Ohtani R, Yoneda K, Furukawa S, Horike N, Kitagawa S, Gaspar AB, Munoz MC, Real JA, Ohba M. Precise control and consecutive modulation of spin transition temperature using chemical migration in porous coordination polymers. J Am Chem Soc 2011; 133: 8600-8605.
- [8] Wu CD, Lin W. Highly Porous, Homochiral Metal-Organic Frameworks: Solvent Exchange Induced Single Crystal to Single Crystal Transformations. Angew Chem Int Ed 2005; 44: 1958-1961.
- [9] Gu, JZ, Kou HZ, Jiang L, Lu TB, Tan MY. Synthesis, structures and magnetic properties of pentanuclear and trinuclear heterometallic complexes with bended and linear cyano-bridges (tren= tris(2-aminoethyl)amine). Inorg Chim Acta 2006; 359: 2015-2022.
- [10] Tanase S, Andruh M, Stanica N, Mathoniere C, Rombaut G, Golhen S, Ouahab L. A novel cyano-bridged pentanuclear complex:[{Mn3(MAC)3(H2O)2}{Fe(CN)6}2]·6H2O·2CH3OH-synthesis, crystal structure and magnetic properties (MAC= pentaaza macrocyclic ligand). Polyhedron 2003; 22: 1315-1320.
- [11] Nakamoto K. Infrared and Raman spectra of inorganic and coordination compounds. Part B., Applications in coordination, organometallic, and bioinorganic chemistry. John Wiley, 2009.
- [12] Şenocak A, Karadağ A, Soylu MS, Andaç Ö. Two novel cyanido-bridged polymeric complexes with suspension bridge type connections and a series of related complex salts: crystallographic and thermal characterizations. New J Chem 2015; 39: 3675-3686.
- [13] Lescouëzec R, Lloret F, Julve M, Vaissermann J, Verdaguer M. [Fe(bipy)(CN)4]- as a Versatile Building Block for the Design of Heterometallic Systems: Synthesis, Crystal Structure, and Magnetic Properties of PPh4[FeIII(bipy)(CN)4]∙H2O,[{FeIII(bipy)(CN)4}2MII(H2O)4]∙4H2O, and [{FeIII(bipy)(CN)4}2ZnII]∙2H2O [bipy= 2, 2'-Bipyridine; M= Mn and Zn]. Inorg chem 2002; 41: 818-826.
- [14] Černák J, Lipkowski J. Potočňák I, Hudák A. Bis-(bis-(1,3-diaminopropane)-copper(II) Tetracyanonickellate(II)) Tetrahydrate: Preparation, Characterization, and Crystal Structure of a Novel Molecular Tetracyanonickellate. Monatsh Chem 2001; 132: 193-202.
- [15] Cernak J, Abboud KA. Ni(bipy)2Ni(CN)4, a new type of one-dimensional square tetracyano complex. Acta Crystallogr C 2000; 56: 783-785.
- [16] Yakuphanoğlu F, Karadağ A, Şekerci M. Investigation of the thermal properties of [Cd(hydet-en)2Pd(CN)4] and [Zn(hydet-en)2Pd(CN)4] single crystals. J Therm Anal Calorim 2006; 86: 727-731.
- [17] Potočňák I, Vavra M, Čižmár E, Tibenská K, Orendáčová A, Steinborn D, Wagner C, Dušek M, Fejfarová K, Schmidt H, Müller T, Orendáč M, Feher A. Low-dimensional compounds containing cyano groups. XIV. Crystal structure, spectroscopic, thermal and magnetic properties of [CuL2][Pt(CN)4] complexes (L=ethylenediamine or N,N-dimethylethylenediamine). J Solid State Chem 2006; 179: 1965-1976.
- [18] Cernak J, Orendáč M, Potočňák I, Chomič J, Orendáčová A, Skoršepa J, Feher A. Cyano complexes with one-dimensional structures: preparations, crystal structures and magnetic properties. Coord Chem Rev 2002; 224: 51-66.
- [19] Vavra M, Potočňák I, Marhefková M, Boča R, Dlháň L. Low-dimensional compounds containing cyanido groups. XXII. Crystal structure, spectroscopic, thermal and magnetic properties of four Cu(II) tetracyanidoplatinates with a typical chain-like structures. Polyhedron 2012; 48; 227-236
- [20] Eriksen J, Hazell A, Jensen A, Jepsen J, Poulsen RD. Bimetallic assemblies, [Ni(en)2]3[M(CN)6]2·3H2O (en= H2NCH2CH2NH2; M = Fe, Co). Acta Crystallogr C 2000; 56: 551-553.
- [21] Miyasaka H, Matsumoto N, Okawa H, Re N, Gallo E, Floriani C. Complexes derived from the reaction of manganese(III) Schiff base complexes and hexacyanoferrate(III): syntheses, multidimensional network structures, and magnetic properties. J Am Chem Soc 1996; 118: 981-994.
- [22] Černák J, Kuchár J, Stolárová M, Kajňaková M, Vavra M, Potočňák I, Falvello LR, Tomás M. Preparation, spectroscopic and magnetic characterization of Cu(cyclam)M(CN)4 complexes exhibiting one-dimensional crystal structures (cyclam= 1, 4, 8, 11-tetraazacyclotetradecane, M= Ni, Pd, Pt). Transit Met Chem 2010; 35: 737-744.
- [23] Muga I, Gutiérrez-Zorrilla JM, Vitoria P, Román P, Lezama L, Beitia JL. Unusual Two Dimensional Nickel(II) Complexes Based on [Ni(dien)]2+ and [M(CN)4]2- Building Blocks (M = Ni, Pd and Pt)- Synthesis, Structural Diversity and Magnetic Properties. European J Inorg Chem 2004; 2004: 1886-1893.
- [24] Pickardt J, Staub B. Kristallstruktur des cyanoverbrückten polymeren Zinkcyanid-Pyridin-Komplexes [Zn(py)2][Zn(CN)4]. Z für Naturforsch - B J Chem Sci 1995; 50: 1517-1520.
- [25] Iwamoto T. Past, present and future of the clathrate inclusion compounds built of cyanometallate hosts. J Incl Phenom Macrocycl Chem 1996; 24: 61-132.
- [26] Marinescu G, Madalan AM, Tiseanu C, Andruh M. New d10 heterometallic coordination polymers based on compartmental Schiff-base ligands. Synthesis, structure and luminescence. Polyhedron 2011; 30: 1070-1075.
- [27] Lefebvre J, Batchelor RJ, Leznoff DB. Cu[Au(CN)2]2(DMSO)2: Golden polymorphs that exhibit vapochromic behavior. J Am Chem Soc 2004; 126: 16117-16125.
- [28] Molnár G, Kitazawa T, Dubrovinsky L, McGarvey JJ, Bousseksou A. Pressure tuning Raman spectroscopy of the spin crossover coordination polymer Fe(C5H5N)2Ni(CN)4]. J Phys: Condens Matter 2004; 16: S1129.
- [29] Rigo P, Bressan M. Cyanide complexes of nickel(II) with hybrid bidentate ligands containing phosphorus and nitrogen or sulfur donor atoms. Inorg Chem 1975; 14: 1491-1494.
- [30] Stocker FB, Troester M, Britton, D. Crystal Structures of a Family of New Copper(I) Cyanide Complexes of Thiourea and Substituted Thioureas. Inorg Chem 1996; 35: 3145-3153.
- [31] Sayın E, Kürkçüoğlu GS, Yeşilel OZ, Hökelek T, Büyükgüngör O. One-and two-dimensional heteropolynuclear complexes with tetracyanonickelate(II) and 2-pyridinemethanol. Z Kristallogr Cryst Mater 2014; 229: 563-572.
- [32] Sayın E, Kürkçüoğlu GS, Yeşilel OZ, Hökelek T. 1D cyanide complexes with 2-pyridinemethanol: Synthesis, crystal structures and spectroscopic properties. J Mol Struct 2015; 1101: 73-81.
- [33] E. Sayın, G.S. Kürkçüoğlu, Syntheses, structures and physical properties of cyanide-bridged M(II)-Ni(II) bimetallic complexes with 2-pyridineethanol (M(II)= Fe, Co and Ni). Anadolu University Journal of Science and Technology A-Applied Sciences and Engineering 17; 2016: 37-49.
- [34] Arjunan V, Balamourougane PS, Govindaraja ST, Mohan S. A comparative study on vibrational, conformational and electronic structure of 2-(hydroxymethyl)pyridine and 3-(hydroxymethyl)pyridine. J Mol Struct 2012; 1018: 156-170.
- [35] Karaağaç D, Kürkçüoğlu GS. Syntheses, spectroscopic and thermal analyses of the hofmann-type metal(II) tetra-cyanonickelate(II) pyridazine complexes:{[M(pdz)Ni(CN)4]∙H2O}n (M= Zn(II) or Cd(II)). Bull Chem Soc Ethiop 2015; 29: 415-422.
- [36] Kürkçüoğlu GS, Yeşilel OZ, Büyükgüngör O. Syntheses, spectral and thermal analyses of heteronuclear aqua(2-methylpyrazine)metal(II) complexes with tetracyanonickelate ion and crystal structure of supramolecular [Cd(H2O)(2mpz)Ni(μ-CN)4]n complex. Struct Chem 2008; 19: 879-888.
- [37] Yılmaz VT, Güney S, Andaç Ö, Harrison WTA. Different coordination modes of saccharin in the metal complexes with 2-pyridylmethanol: synthesis, spectroscopic, thermal and structural characterization. Polyhedron 2002; 21: 2393-2402.
- [38] Anderson, RJ, Bendell DJ, Groundwater PW. Organic spectroscopic analysis (Vol. 22). Royal Society of Chemistry 2004.
- [39] Socrates, G., Infrared and Raman characteristic group frequencies: tables and charts. John Wiley & Sons 2004.
- [40] Ciajolo A, Apicella B, Barbella R, Tregross, A. Correlations of the spectroscopic properties with the chemical composition of flame-formed aromatic mixtures. Combust Sci Technol 2000; 153: 19-32.
- [41] Guchhait N, Ebata T, Mikami N. Structures of hydrogen-bonded clusters of benzyl alcohol with water investigated by infrared-ultraviolet double resonance spectroscopy in supersonic jet. J Chem Phys 1999; 111: 8438-8447.
- [42] Puviarasan N, Arjunan V. Mohan S. FT-IR and FT-Raman studies on 3-aminophthalhydrazide and N-aminophthalimide. Turk J Chem 2002; 26: 323-334.
- [43] Roeges NP. A guide to the complete interpretation of infrared spectra of organic structures. Wiley 1994.
- [44] Xiao-Hong L, Hong-Ling C, Rui-Zhou Z, Xian-Zhou Z. Theoretical investigation on the non-linear optical properties, vibrational spectroscopy and frontier molecular orbital of (E)-2-cyano-3-(3-hydroxyphenyl) acrylamide molecule. Spectrochim Acta A Mol Biomol Spectrosc 2015; 137: 321-327.
- [45] Silverstein R, Webster F. Spectrometric identification of organic compounds. John Wiley & Sons 2006.
- [46] Saxena R, Kandpal L, Mathur G. Synthesis and characterization of poly(benzobisthiazole)s derived from halogenated phthalic acid and isophthalic acid. J Polym Sci A Polym Chem 2002; 40: 3959-3966.
- [47] Prasad M, Sri NU, Veeraiah V. A combined experimental and theoretical studies on FT-IR, FT-Raman and UV-vis spectra of 2-chloro-3-quinolinecarboxaldehyde. Spectrochim Acta A Mol Biomol Spectrosc 2015; 148: 163-174.
- [48] Parlak C. FT-IR and Raman spectroscopic analysis of some Hofmann type complexes. Spectrochim Acta A Mol Biomol Spectrosc 2012; 99: 12-17.
- [49] Suzuki, S. Orvilelle-TW. Molecular force field of pyridine and its application to pyridine-metal complexes. J Mol Struct 1977; 37: 321-327.
- [50] Gör K, Kürkçüoğlu GS, Yeşilel OZ, Büyükgüngör O. Syntheses, crystal structures and spectroscopic properties of cyano-bridged two-dimensional coordination polymers with 3-methylpyridazine. Inorg Chim Acta 2014; 414: 15-20.
- [51] McCullough RL. Jones LH, Crosby, GA. An analysis of the vibrational spectrum of the tetracyanonickelate(II) ion in a crystal lattice. SpectrochimActa, 1960; 16: 929-944.
- [52] Kürkçüoğlu GS, Sayın E, Şahin O. Cyanide bridged hetero-metallic polymeric complexes: Syntheses, vibrational spectra, thermal analyses and crystal structures of complexes [M(1,2-dmi)2Ni(μ-CN)4]n (M= Zn (II) and Cd (II)). J Mol Struct 2015; 1101: 82-90.
- [53] Kubas GJ, Jones LH. Potential constants of the tetracyanide ions of nickel, palladium, and platinum. Inorg Chem 1974; 13: 2816-2819.
- [54] Kuchar J, Cernak J, Abboud KA. The one-dimensional structure of Cu(dmen)2Pd(CN)4 (dmen is N,N-dimethylethylenediamine). Acta Crystallogr C 2004; 60: M492-M494.
- [55] Karaağaç D, Kürkçüoğlu GS, Yeşilel OZ, Hökelek T, Dal H. Synthesis and crystal structure of cyano-bridged three dimensional polyheteronuclear complex. Z Kristallogr 2012; 227: 639-645.
- [56] Karadağ A, Şenocak A, Önal İ, Yerli Y, Şahin E, Başaran AC, Preparation, structural, magnetic and thermal properties of two heterobimetallic cyano-bridged nickel(II)-copper (II)/platinum(II) coordination polymers. Inorg Chim Acta 2009; 362: 2299-2304.
- [57] Nakamoto K. Infrared and Raman spectra of coordination compounds. Wiley, New York 1997.
- [58] Molnár G, Niel V, Gaspar AB, Real JA, Zwick A, Bousseksou A, McGarvey JJ. Vibrational spectroscopy of cyanide-bridged, iron(II) spin-crossover coordination polymers: Estimation of vibrational contributions to the entropy change associated with the spin transition. J Phys Chem B 2002; 106: 9701-9707.
- [59] Kürkçüoğlu GS, Kiraz FÇ, Sayın E. Vibrational spectra, powder X-ray diffractions and physical properties of cyanide complexes with 1-ethylimidazole. Spectrochim Acta A Mol Biomol Spectrosc 2015; 149: 8-16.
SYNTHESIS, CHARACTERIZATION OF CYANIDE COMPLEXES WITH 2-(HYDROXYMETHYL)PYRIDINE BY VIBRATIONAL SPECTROSCOPIC, THERMAL STUDIES AND ELECTRICAL PROPERTIES
Year 2023,
Volume: 24 Issue: 4 - Eskişehir Technical University Journal of Science and Technology A - Applied Sciences and Engineering, 216 - 229, 27.12.2023
Elvan Sayın
,
Güneş Süheyla Kürkçüoğlu
References
- [1] Batten SR, Neville SM, Turner DR. Coordination polymers: design, analysis and application. Royal Society of Chemistry, 2009.
- [2] Tadokoro M, Yasuzukara S, Nakamura M, Shinoda T, Tatenuma T, Mitsumi M, Ozawa Y, Toriumi K, Yoshino H, Shiomi D, Sato K, Takui T, Mori T, Murata K. A High Conductivity Crystal Containing a Copper(I) Coordination Polymer Bridged by the Organic Acceptor TANC. Angew Chem 2006; 118: 5268-5271.
- [3] Gapud AA, Weber AP, Alexandera JA, Pham L, Khan A, Leatherbury RI, Reyes AP, Lumata LL, Kuhns PL, Valente EJ, Sykora RE. New quasi-one-dimensional tetracyanidoplatinate, Cs4[Pt(CN)4](CF3SO3)2: Synthesis, structure, and physical characterization. J Phys Chem Solids 2014; 75: 447-452.
- [4] Janiak C. Engineering coordination polymers towards applications. Dalton Trans 2003; 14: 2781-2804.
- [5] Di Noto V, Vittadello M, Greenbaum SG, Suares S, Kano K, Furukawa T. A new class of lithium hybrid gel electrolyte systems. J Phys Chem B 2004; 108: 18832-18844.
- [6] Real JA, Gaspar AB, Munoz MC. Thermal, pressure and light switchable spin-crossover materials. Dalton Trans 2005; 12: 2062-2079.
- [7] Ohtani R, Yoneda K, Furukawa S, Horike N, Kitagawa S, Gaspar AB, Munoz MC, Real JA, Ohba M. Precise control and consecutive modulation of spin transition temperature using chemical migration in porous coordination polymers. J Am Chem Soc 2011; 133: 8600-8605.
- [8] Wu CD, Lin W. Highly Porous, Homochiral Metal-Organic Frameworks: Solvent Exchange Induced Single Crystal to Single Crystal Transformations. Angew Chem Int Ed 2005; 44: 1958-1961.
- [9] Gu, JZ, Kou HZ, Jiang L, Lu TB, Tan MY. Synthesis, structures and magnetic properties of pentanuclear and trinuclear heterometallic complexes with bended and linear cyano-bridges (tren= tris(2-aminoethyl)amine). Inorg Chim Acta 2006; 359: 2015-2022.
- [10] Tanase S, Andruh M, Stanica N, Mathoniere C, Rombaut G, Golhen S, Ouahab L. A novel cyano-bridged pentanuclear complex:[{Mn3(MAC)3(H2O)2}{Fe(CN)6}2]·6H2O·2CH3OH-synthesis, crystal structure and magnetic properties (MAC= pentaaza macrocyclic ligand). Polyhedron 2003; 22: 1315-1320.
- [11] Nakamoto K. Infrared and Raman spectra of inorganic and coordination compounds. Part B., Applications in coordination, organometallic, and bioinorganic chemistry. John Wiley, 2009.
- [12] Şenocak A, Karadağ A, Soylu MS, Andaç Ö. Two novel cyanido-bridged polymeric complexes with suspension bridge type connections and a series of related complex salts: crystallographic and thermal characterizations. New J Chem 2015; 39: 3675-3686.
- [13] Lescouëzec R, Lloret F, Julve M, Vaissermann J, Verdaguer M. [Fe(bipy)(CN)4]- as a Versatile Building Block for the Design of Heterometallic Systems: Synthesis, Crystal Structure, and Magnetic Properties of PPh4[FeIII(bipy)(CN)4]∙H2O,[{FeIII(bipy)(CN)4}2MII(H2O)4]∙4H2O, and [{FeIII(bipy)(CN)4}2ZnII]∙2H2O [bipy= 2, 2'-Bipyridine; M= Mn and Zn]. Inorg chem 2002; 41: 818-826.
- [14] Černák J, Lipkowski J. Potočňák I, Hudák A. Bis-(bis-(1,3-diaminopropane)-copper(II) Tetracyanonickellate(II)) Tetrahydrate: Preparation, Characterization, and Crystal Structure of a Novel Molecular Tetracyanonickellate. Monatsh Chem 2001; 132: 193-202.
- [15] Cernak J, Abboud KA. Ni(bipy)2Ni(CN)4, a new type of one-dimensional square tetracyano complex. Acta Crystallogr C 2000; 56: 783-785.
- [16] Yakuphanoğlu F, Karadağ A, Şekerci M. Investigation of the thermal properties of [Cd(hydet-en)2Pd(CN)4] and [Zn(hydet-en)2Pd(CN)4] single crystals. J Therm Anal Calorim 2006; 86: 727-731.
- [17] Potočňák I, Vavra M, Čižmár E, Tibenská K, Orendáčová A, Steinborn D, Wagner C, Dušek M, Fejfarová K, Schmidt H, Müller T, Orendáč M, Feher A. Low-dimensional compounds containing cyano groups. XIV. Crystal structure, spectroscopic, thermal and magnetic properties of [CuL2][Pt(CN)4] complexes (L=ethylenediamine or N,N-dimethylethylenediamine). J Solid State Chem 2006; 179: 1965-1976.
- [18] Cernak J, Orendáč M, Potočňák I, Chomič J, Orendáčová A, Skoršepa J, Feher A. Cyano complexes with one-dimensional structures: preparations, crystal structures and magnetic properties. Coord Chem Rev 2002; 224: 51-66.
- [19] Vavra M, Potočňák I, Marhefková M, Boča R, Dlháň L. Low-dimensional compounds containing cyanido groups. XXII. Crystal structure, spectroscopic, thermal and magnetic properties of four Cu(II) tetracyanidoplatinates with a typical chain-like structures. Polyhedron 2012; 48; 227-236
- [20] Eriksen J, Hazell A, Jensen A, Jepsen J, Poulsen RD. Bimetallic assemblies, [Ni(en)2]3[M(CN)6]2·3H2O (en= H2NCH2CH2NH2; M = Fe, Co). Acta Crystallogr C 2000; 56: 551-553.
- [21] Miyasaka H, Matsumoto N, Okawa H, Re N, Gallo E, Floriani C. Complexes derived from the reaction of manganese(III) Schiff base complexes and hexacyanoferrate(III): syntheses, multidimensional network structures, and magnetic properties. J Am Chem Soc 1996; 118: 981-994.
- [22] Černák J, Kuchár J, Stolárová M, Kajňaková M, Vavra M, Potočňák I, Falvello LR, Tomás M. Preparation, spectroscopic and magnetic characterization of Cu(cyclam)M(CN)4 complexes exhibiting one-dimensional crystal structures (cyclam= 1, 4, 8, 11-tetraazacyclotetradecane, M= Ni, Pd, Pt). Transit Met Chem 2010; 35: 737-744.
- [23] Muga I, Gutiérrez-Zorrilla JM, Vitoria P, Román P, Lezama L, Beitia JL. Unusual Two Dimensional Nickel(II) Complexes Based on [Ni(dien)]2+ and [M(CN)4]2- Building Blocks (M = Ni, Pd and Pt)- Synthesis, Structural Diversity and Magnetic Properties. European J Inorg Chem 2004; 2004: 1886-1893.
- [24] Pickardt J, Staub B. Kristallstruktur des cyanoverbrückten polymeren Zinkcyanid-Pyridin-Komplexes [Zn(py)2][Zn(CN)4]. Z für Naturforsch - B J Chem Sci 1995; 50: 1517-1520.
- [25] Iwamoto T. Past, present and future of the clathrate inclusion compounds built of cyanometallate hosts. J Incl Phenom Macrocycl Chem 1996; 24: 61-132.
- [26] Marinescu G, Madalan AM, Tiseanu C, Andruh M. New d10 heterometallic coordination polymers based on compartmental Schiff-base ligands. Synthesis, structure and luminescence. Polyhedron 2011; 30: 1070-1075.
- [27] Lefebvre J, Batchelor RJ, Leznoff DB. Cu[Au(CN)2]2(DMSO)2: Golden polymorphs that exhibit vapochromic behavior. J Am Chem Soc 2004; 126: 16117-16125.
- [28] Molnár G, Kitazawa T, Dubrovinsky L, McGarvey JJ, Bousseksou A. Pressure tuning Raman spectroscopy of the spin crossover coordination polymer Fe(C5H5N)2Ni(CN)4]. J Phys: Condens Matter 2004; 16: S1129.
- [29] Rigo P, Bressan M. Cyanide complexes of nickel(II) with hybrid bidentate ligands containing phosphorus and nitrogen or sulfur donor atoms. Inorg Chem 1975; 14: 1491-1494.
- [30] Stocker FB, Troester M, Britton, D. Crystal Structures of a Family of New Copper(I) Cyanide Complexes of Thiourea and Substituted Thioureas. Inorg Chem 1996; 35: 3145-3153.
- [31] Sayın E, Kürkçüoğlu GS, Yeşilel OZ, Hökelek T, Büyükgüngör O. One-and two-dimensional heteropolynuclear complexes with tetracyanonickelate(II) and 2-pyridinemethanol. Z Kristallogr Cryst Mater 2014; 229: 563-572.
- [32] Sayın E, Kürkçüoğlu GS, Yeşilel OZ, Hökelek T. 1D cyanide complexes with 2-pyridinemethanol: Synthesis, crystal structures and spectroscopic properties. J Mol Struct 2015; 1101: 73-81.
- [33] E. Sayın, G.S. Kürkçüoğlu, Syntheses, structures and physical properties of cyanide-bridged M(II)-Ni(II) bimetallic complexes with 2-pyridineethanol (M(II)= Fe, Co and Ni). Anadolu University Journal of Science and Technology A-Applied Sciences and Engineering 17; 2016: 37-49.
- [34] Arjunan V, Balamourougane PS, Govindaraja ST, Mohan S. A comparative study on vibrational, conformational and electronic structure of 2-(hydroxymethyl)pyridine and 3-(hydroxymethyl)pyridine. J Mol Struct 2012; 1018: 156-170.
- [35] Karaağaç D, Kürkçüoğlu GS. Syntheses, spectroscopic and thermal analyses of the hofmann-type metal(II) tetra-cyanonickelate(II) pyridazine complexes:{[M(pdz)Ni(CN)4]∙H2O}n (M= Zn(II) or Cd(II)). Bull Chem Soc Ethiop 2015; 29: 415-422.
- [36] Kürkçüoğlu GS, Yeşilel OZ, Büyükgüngör O. Syntheses, spectral and thermal analyses of heteronuclear aqua(2-methylpyrazine)metal(II) complexes with tetracyanonickelate ion and crystal structure of supramolecular [Cd(H2O)(2mpz)Ni(μ-CN)4]n complex. Struct Chem 2008; 19: 879-888.
- [37] Yılmaz VT, Güney S, Andaç Ö, Harrison WTA. Different coordination modes of saccharin in the metal complexes with 2-pyridylmethanol: synthesis, spectroscopic, thermal and structural characterization. Polyhedron 2002; 21: 2393-2402.
- [38] Anderson, RJ, Bendell DJ, Groundwater PW. Organic spectroscopic analysis (Vol. 22). Royal Society of Chemistry 2004.
- [39] Socrates, G., Infrared and Raman characteristic group frequencies: tables and charts. John Wiley & Sons 2004.
- [40] Ciajolo A, Apicella B, Barbella R, Tregross, A. Correlations of the spectroscopic properties with the chemical composition of flame-formed aromatic mixtures. Combust Sci Technol 2000; 153: 19-32.
- [41] Guchhait N, Ebata T, Mikami N. Structures of hydrogen-bonded clusters of benzyl alcohol with water investigated by infrared-ultraviolet double resonance spectroscopy in supersonic jet. J Chem Phys 1999; 111: 8438-8447.
- [42] Puviarasan N, Arjunan V. Mohan S. FT-IR and FT-Raman studies on 3-aminophthalhydrazide and N-aminophthalimide. Turk J Chem 2002; 26: 323-334.
- [43] Roeges NP. A guide to the complete interpretation of infrared spectra of organic structures. Wiley 1994.
- [44] Xiao-Hong L, Hong-Ling C, Rui-Zhou Z, Xian-Zhou Z. Theoretical investigation on the non-linear optical properties, vibrational spectroscopy and frontier molecular orbital of (E)-2-cyano-3-(3-hydroxyphenyl) acrylamide molecule. Spectrochim Acta A Mol Biomol Spectrosc 2015; 137: 321-327.
- [45] Silverstein R, Webster F. Spectrometric identification of organic compounds. John Wiley & Sons 2006.
- [46] Saxena R, Kandpal L, Mathur G. Synthesis and characterization of poly(benzobisthiazole)s derived from halogenated phthalic acid and isophthalic acid. J Polym Sci A Polym Chem 2002; 40: 3959-3966.
- [47] Prasad M, Sri NU, Veeraiah V. A combined experimental and theoretical studies on FT-IR, FT-Raman and UV-vis spectra of 2-chloro-3-quinolinecarboxaldehyde. Spectrochim Acta A Mol Biomol Spectrosc 2015; 148: 163-174.
- [48] Parlak C. FT-IR and Raman spectroscopic analysis of some Hofmann type complexes. Spectrochim Acta A Mol Biomol Spectrosc 2012; 99: 12-17.
- [49] Suzuki, S. Orvilelle-TW. Molecular force field of pyridine and its application to pyridine-metal complexes. J Mol Struct 1977; 37: 321-327.
- [50] Gör K, Kürkçüoğlu GS, Yeşilel OZ, Büyükgüngör O. Syntheses, crystal structures and spectroscopic properties of cyano-bridged two-dimensional coordination polymers with 3-methylpyridazine. Inorg Chim Acta 2014; 414: 15-20.
- [51] McCullough RL. Jones LH, Crosby, GA. An analysis of the vibrational spectrum of the tetracyanonickelate(II) ion in a crystal lattice. SpectrochimActa, 1960; 16: 929-944.
- [52] Kürkçüoğlu GS, Sayın E, Şahin O. Cyanide bridged hetero-metallic polymeric complexes: Syntheses, vibrational spectra, thermal analyses and crystal structures of complexes [M(1,2-dmi)2Ni(μ-CN)4]n (M= Zn (II) and Cd (II)). J Mol Struct 2015; 1101: 82-90.
- [53] Kubas GJ, Jones LH. Potential constants of the tetracyanide ions of nickel, palladium, and platinum. Inorg Chem 1974; 13: 2816-2819.
- [54] Kuchar J, Cernak J, Abboud KA. The one-dimensional structure of Cu(dmen)2Pd(CN)4 (dmen is N,N-dimethylethylenediamine). Acta Crystallogr C 2004; 60: M492-M494.
- [55] Karaağaç D, Kürkçüoğlu GS, Yeşilel OZ, Hökelek T, Dal H. Synthesis and crystal structure of cyano-bridged three dimensional polyheteronuclear complex. Z Kristallogr 2012; 227: 639-645.
- [56] Karadağ A, Şenocak A, Önal İ, Yerli Y, Şahin E, Başaran AC, Preparation, structural, magnetic and thermal properties of two heterobimetallic cyano-bridged nickel(II)-copper (II)/platinum(II) coordination polymers. Inorg Chim Acta 2009; 362: 2299-2304.
- [57] Nakamoto K. Infrared and Raman spectra of coordination compounds. Wiley, New York 1997.
- [58] Molnár G, Niel V, Gaspar AB, Real JA, Zwick A, Bousseksou A, McGarvey JJ. Vibrational spectroscopy of cyanide-bridged, iron(II) spin-crossover coordination polymers: Estimation of vibrational contributions to the entropy change associated with the spin transition. J Phys Chem B 2002; 106: 9701-9707.
- [59] Kürkçüoğlu GS, Kiraz FÇ, Sayın E. Vibrational spectra, powder X-ray diffractions and physical properties of cyanide complexes with 1-ethylimidazole. Spectrochim Acta A Mol Biomol Spectrosc 2015; 149: 8-16.