Research Article
BibTex RIS Cite

Synthesis, Characterization, Spectral Analysis and Molecular Simulation Studies of compounds formed by 2-mercaptopyridine and 1,4-dioxane ligands with some metal(II) chlorides

Year 2024, Volume: 37 Issue: 4, 2036 - 2060, 01.12.2024

Zeki Kartal , Zarife Sibel Şahin

https://doi.org/10.35378/gujs.1359705

Abstract

In this investigation, two novel coordination compounds in crystalline form were synthesized utilizing chemical substances including 2-mercaptopyridine (2MP), 1,4-dioxane (pD), nickel(II) chloride (NiCl2), and cadmium(II) chloride (CdCl2), followed by an exploration of their structural properties through various experimental techniques. In addition, molecular modelling studies were carried out with B3LYP/LanL2DZ level using Gaussian 03 program. HOMO and LUMO orbitals, NBO studies were obtained by computation. The results from both experimental and optimized structural data were consistent. In particular, the vibration frequencies obtained experimentally of these compounds and the vibration frequencies theoretically calculated with B3LYP/LanL2DZ are substantially compatible with each other.

Keywords

2-mercaptopyridine 2-pyridinethiolate 1 4-dioxane molecular simulation SC-XRD analysis

References

  • [1] Batten, S.R., Champness, N.R., Chen, X.M., Garcia-Martinez, J., Kitagawa, S., Öhrström, L., O’Keeffe, M., Suh, P., Reedijk, J., “Terminology of metal–organic frameworks and coordination polymers (IUPAC Recommendations 2013)”, Pure and Applied Chemistry, 85(8): 1715-1724, (2013). DOI: https://doi.org/10.1351/PAC-REC-12-11-20
  • [2] Fromm, K., “Coordination polymer networks with s-block metal ions”, Coordination Chemistry Reviews; 252 (8–9): 856-885, (2008). DOI: https://doi.org/10.1016/j.ccr.2007.10.032
  • [3] Yang, Y., Jiang, G., Li, Y.Z., Bai, J., Pan, Y., You, X.Z., “Synthesis, structures and properties of alkaline earth metal benzene-1.4-dioxylacetates with three-dimensional hybrid networks”, Inorganica Chimica Acta, 359(10): 3257-3263, (2006). DOI: https://doi.org/10.1016/j.ica.2006.03.038
  • [4] Adams, E.J., Skrydstrup. T., Lindsay, K.B., “2-Pyridinethiol, Encyclopedia of Reagents for Organic Synthesis”, (2005). DOI: https://doi.org/10.1002/047084289X.rp286
  • [5] Shunmugam, R., Sathyanarayana, D.N., “Raman and polarized infrared spectra of pyridine-2-thione”, Spectrochimica Acta Part A: Molecular Spectroscopy, 40(8):757-761, (1984). DOI: https://doi.org/10.1016/0584-8539(84)80100-2
  • [6] Castiñiras, A., Hiller, W., Strähle, J., Bravo, J., Casas, J., Gayoso, M., Sordo, J., “Methyl- and phenyl-mercury(II) derivatives of 2-mercaptopyridine. Crystal and molecular structure of methyl(pyridine-2-thiolato)mercury(II)”, Journal of the Chemical Society, Dalton Transactions, 9:1945-1948, (1986). DOI: https://doi.org/10.1039/dt9860001945
  • [7] Toma, H.E., Santos, P.S., Mattioli, M.P.D., Oliveira, L.A.A., “Kinetics, electrochemistry and resonance raman spectra of the (2-mercaptopyridine) (edta)ruthenium(III) complex”, Polyhedron, 6(3): 603-611, (1987). DOI: https://doi.org/10.1016/S0277-5387(00)81031-1
  • [8] Baldwin, J.A., Vlčková, B., Andrews, M.P., Butler, S., “Surface-Enhanced Raman Scattering of Mercaptopyridines and Pyrazinamide Incorporated in Silver Colloid−Adsorbate Films”, Langmuir, 13(14):3744-3751, (1997). DOI: https://doi.org/10.1021/la960719d
  • [9] Pang, Y.S., Hwang, H.J., Kim, M.S., “Adsorption of 2-mercaptopyridine and 2-mercaptopyrimidine on a silver colloidal surface investigated by Raman spectroscopy”, Journal of Molecular Structure, 441(1): 63-76, (1998). DOI: https://doi.org/10.1016/s0022-2860(97)00280-9
  • [10] Zhang, H.L., Evans, S.D., Henderson, J.R., Miles, R.E., Shen, T.H., “Spectroscopic Characterization of Gold Nanoparticles Passivated by Mercaptopyridine and Mercaptopyrimidine Derivatives”, The Journal of Physical Chemistry B, 107(25): 6087-6095, (2003). DOI: https://doi.org/ 10.1002/Adma.200390124
  • [11] Ozturk, I.I., Kourkoumelis, N., Hadjikakou, S.K., Manos, M.J., Tasiopoulos, A.J., Butler, I.S., Balzarini, J., Hadjiliadis, N., “Interaction of antimony(III) chloride with thiourea, 2-mercapto-5-methyl-benzimidazole, 3-methyl-2-mercaptobenzothiazole, 2-mercaptopyrimidine, and 2-mercaptopyridine”, Journal of Coordination Chemistry, 64(22): 3859-3871, (2011). DOI: https://doi.org/10.1080/00958972.2011.633603
  • [12] Do, W.H., Lee, C.J., Kim, D.Y., Jung, M.J., “Adsorption of 2-mercaptopyridine and 4-mercaptopyridine on a silver surfaces investigated by SERS spectroscopy”, Journal of Industrial and Engineering Chemistry, 18(6): 2141-2146, (2012). DOI: https://doi.org/10.1016/j.jiec.2012.06.009
  • [13] Naktode, K., Reddy, T.D.N., Nayek, H.P., Mallik, B.S., Panda, T.K., “Heavier group 2 metal complexes with a flexible scorpionate ligand based on 2-mercaptopyridine”, Royal Society of Chemistry Advances, 5(63): 51413-51420, (2015). DOI: https://doi.org/10.1039/C5RA04696C
  • [14] Ramsay, D.A., “The Vibration Spectrum and Molecular Configuration of 1,4-dioxane”. Proceedings of the Royal Society of London A, 190: 562-574, (1947). DOI: https://doi.org/10.1098/rspa.1947.0097
  • [15] Malherbe, F.E., Bernstein, H.J., “The Infrared and Raman Spectra of p-Dioxane”, Journal of the American Chemical Society, 74(17): 4408-4410, (1952). DOI: https://doi.org/10.1021/ja01137a051
  • [16] Snyder, R.G., Zerbi, G., “Vibrational analysis of ten simple aliphatic ethers: Spectra, assignments, valence force field and molecular conformations”, Spectrochimica Acta Part A: Molecular Spectroscopy, 23(2): 391-437, (1967). DOI: https://doi.org/10.1016/0584-8539(67)80241-1
  • [17] Ellestad, O.H., Klaboe, P., Hagen, G., “The vibrational spectra of 1,4-dioxan-do and 1,4- dioxan-d8”, Spectrochimica Acta, 27A: 1025-1048, (1971). DOI: https://doi.org/10.1016/0584-8539(71)80186-1
  • [18] Karayannis, N.M., Mikulski, C.M., Speca, A.N., Cronin, J.T., Pytlewski, L.L., “p-Dioxane, p-thioxane, and 1,2-dimethoxyethane complexes with transition metal perchlorates”, Inorganic Chemistry, 11(10): 2330-2335, (1972). DOI: https://doi.org/10.1021/ic50116a008
  • [19] Shimanouchi, T., “Tables of molecular vibrational frequencies consolidated volume II”, Journal of Physical and Chemical Reference Data., 6(3): 993-1102, (1977). DOI: https://doi.org/10.1063/1.555560
  • [20] Schwarz, W., Schmidt, A., Binder, G.E., “1,4-Dioxan•H2O•SbCl5; Vibrational Spectra, Crystal and Molecular Structure”, Zeitschrift für Naturforschung B, 33(2): 136-139, (1978). DOI: https://doi.org/10.1515/znb-1978-0202
  • [21] Dempster, A.B., Uslu, H., “Infrared spectra and stability of Hofmann-type dioxane clathrates”, Spectrochimica Acta Part A: Molecular Spectroscopy, 34(1): 71-75, (1978). DOI: https://doi.org/10.1016/0584-8539(78)80188-3
  • [22] Den, H.M., Driessen, W.L., “Ethers as ligands, Part IV, Metal(II) 1,4-dioxane solvates”, Inorganica Chimica Acta, 39:43-46, (1980). DOI: https://doi.org/10.1016/s0020-1693(00)93631-4
  • [23] Parvez, M., Pajerski, A.D., Richey, H.G., “(Dioxane)dineopentylmagnesium: a polymeric structure”, Acta Crystallographica Section C Crystal Structure Communications, 44(7): 1212-1215, (1998). DOI: https://doi.org/10.1107/s0108270188003099
  • [24] Edelmann, F.T., Pauer, F., Wedler, M., Stalke, D., “Preparation and structural characterization of dioxane-coordinated alkali metal bis(trimethylsilyl)amides”, Inorganic Chemistry, 31(20): 4143-4146, (1992). DOI: https://doi.org/10.1021/ic00046a028
  • [25] Parlak, C., Alver, Ö., “Spectroscopic investigations of 1,4-dioxane adsorbed on bentonite from Anatolia”, Anadolu University Journal of Science and Technology A - Applied Sciences and Engineering, 17(2): 273-277, (2016). DOI: https://doi.org/10.18038/btda,87236
  • [26] Borowski, P., Gac, W., Pulay, P., Wolinski, K., “The vibrational spectrum of 1,4-dioxane in aqueous solution – theory and experiment”, New Journal of Chemistry, 40(9): 7663-7670, (2016). DOI: https://doi.org/10.1039/c6nj01198e
  • [27] Kartal, Z., Yavuz, A., “The synthesis and the spectroscopic, thermal, and structural properties of the M2[(fumarate)Ni(CN)4]•2(1,4-Dioxane) clathrate (M = Co, Ni, Cd and Hg)”, Journal of Molecular Structure, 1155: 171-183, (2018). DOI: https://doi.org/10.1016/j.molstruc.2017.10.107
  • [28] Lockwood, D.J., Bertrand, D., Carrara, P., Mischler, G., Billerey, D., Terrier, C., “Raman spectrum of NiCl2”, Journal of Physics C: Solid State Physics, 11(17): 3615-3620, (1979). DOI: https://doi.org/10.1088/0022-3719/12/17/031
  • [29] Agulló-Rueda, F., Calleja, J.M., Martini, M., Spinolo, G., Cariati, F., “Raman and infrared spectra of transition metal halide hexahydrates”, Journal of Raman Spectroscopy, 18(7): 485-491, (1987). DOI: https://doi.org/10.1002/jrs.1250180707
  • [30] Lide, D.R., “CRC Handbook of Chemistry and Physics”, 90th ed, Boca Raton, Florida, USA: CRC Press, ISBN 978-1-4200-9084-0, (2009).
  • [31] Seidell, A., “Solubilities of Inorganic and Organic Compounds: A Compilation of Quantitave Solubility Data From the Periodical Literature; Volume 1”, Legare Street Press, ISBN-10: 1015948987, (2022).
  • [32] Greenwood, N.N., Earnshaw, A., “Chemistry of the Elements”, 2nd ed, Butterworth-Heinemann, Oxford, UK: ISBN: 9780750633659. (1997).
  • [33] Wells, A.F., “Structural Inorganic Chemistry”, 4th ed, Oxford University Press, Oxford, UK: ISBN: 0198553544, (1975).
  • [34] Smith, M.B., March, J., “March’s Advanced Organic Chemistry: Reactions, Mechanisms, and Structure”. 6th ed., Wiley, New York, USA: ISBN-10: 0471720917, (2007).
  • [35] Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Montgomery, Jr.J.A., Vreven, T., Kudin, K.N., Burant, J.C., Millam, J.M., Iyengar, S.S., Tomasi, J., Barone, V., Mennucci, B., Cossi, M., Scalmani, G., Rega, N., Petersson, G.A., Nakatsuji, H., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Klene, M., Li, X., Knox, J.E., Hratchian, H. P., Cross, J.B., Bakken, V., Adamo, C., Jaramillo, J., Dapprich, S., Daniels, A.D., Strain, M.C., Farkas, O., Malick, D.K., Rabuck, A.D., Raghavachari, K., Foresman, J.B., Ortiz, J.V., Cui, Q., Baboul, A.G., Clifford, S., Cioslowski, J., Stefanov, B.B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., Martin, R.L., Fox, D.J., Keith, T., Al-Laham, M.A., Peng, C.Y., Nanayakkara, A., Challacombe, M., Gill, P.M.W., Johnson, B., Chen, W., Wong, M.W., Gonzalez, C., Pople, J.A., Gaussian 03 Revision D.01. Gaussian, Inc., Wallingford CT, (2004).
  • [36] Young, D.C., “Computational chemistry: a practical guide for applying techniques to real-world problems (electronics)”, New York, USA: Wiley, ISBN:  0-471-33368-9, (2001).
  • [37] Dennington, R., Keith, T., Millam, J., Gauss View, Version 4.1.2. Semichem Inc., Shawnee Mission (2007).
  • [38] Sheldrick, G.M., “A short history of SHELX”, Acta Crystallographica, A64: 112-122, (2008). DOI: https://doi.org/10.1107/S0108767307043930
  • [39] Farrugia, L.J., “WinGX and ORTEP for Windows: an update”, Journal of Applied Crystallography, 45: 849-854, (2012). DOI: https://doi.org/10.1107/S0021889812029111
  • [40] Macrae, C.F., Bruno, I.J., Chisholm, J.A., Edgington, P., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J., Wood, P.A., “Mercury CSD 2.0 – New features for the visualization and investigation of crystal structures”, Journal of Applied Crystallography, 41: 466-470, (2008). DOI: https://doi.org/10.1107/S0021889807067908
  • [41] Sickerman, N.S., Park, Y.J., Ng, G.K.Y., Bates, J.E. Hilkert, M., Ziller, J.W., Furche, F., Borovik, A.S., “Synthesis, structure, and physical properties for a series of trigonal bipyramidal M(II)-Cl complexes with intramolecular hydrogen bonds”, Dalton Transactions, 41(15): 4358-4364, (2012). DOI: https://doi.org/10.1039/c2dt12244h
  • [42] Gusev, A.N., Shul’gin, V.F., Ryush, I.O., Hasegawa, M., Kiskin, M.A., Efimov, N.N., Konstantin, A., Lyssenko, A., Eremenko, I.L., Linert, W., “Copper(II), Nickel(II), and Cobalt(II)/(III) Self-Assembled Polynuclear Complexes of Bis[(pyridin-2-yl)-1,2,4-triazol-3-yl]]methane”, European Journal of Inorganic Chemistry, 3: 704-712, (2017). DOI: https://doi.org/10.1002/ejic.201601107
  • [43] Paes, L.W.C., Suárez, J.A., Márquez, A.M., Sanz, J.F., “First-principles study of nickel complex with 1,3-dithiole-2-thione-4,5-dithiolate ligands as model photosensitizers”, Theoretical Chemistry Accounts, 136(6): 1-9, (2017). DOI: https://doi.org/10.1007/s00214-017-2098-7
  • [44] Hakimi, M., Mardani, Z., Moeini, K., Fernandes, M.A., “Coordination geometries and crystal structures of cadmium(II) complexes with a new amino alcohol (NN′O) ligand”, Journal of Coordination Chemistry, 65(13): 2221-2233, (2012). DOI: https://doi.org/10.1080/00958972.2012.690145
  • [45] Kawasaki, T., Kitazawa, T., “Synthesis and Crystal Structures of Cadmium(II) Cyanide with Branched-Butoxyethanol”, Crystals, 8(5): 221/1-221/10, (2018). https://doi.org/10.3390/cryst8050221
  • [46] BelhajSalah, S., Abdelbaky, M.S.M., García-Granda, S., Essalah, K., Ben Nasr, C., Mrad, M.L., “Crystal structure, Hirshfeld surfaces computational study and physicochemical characterization of the hybrid material (C7H10N)2[SnCl6]•H2O”, Journal of Molecular Structure, 1152: 276-286, (2018). DOI: https://doi.org/10.1016/j.molstruc.2017.09.098
  • [47] Jellali, A., Elleuch, S., Hamdi, B., Zouari, R., “Experimental and theoretical investigations of the molecular structure, the spectroscopic properties and TD-DFT analysis of a new semiconductor hybrid based iron (III)”, Journal of Saudi Chemical Society, 23(5): 600-611, (2019). DOI: https://doi.org/10.1016/j.jscs.2018.10.006
  • [48] Zhang, W., Schmid, T., Yeo, B.S., Zenobi, R., “Tip-enhanced Raman spectroscopy reveals rich nanoscale adsorption chemistry of 2-mercaptopyridine on Ag”, Israel Journal of Chemistry, 47(2): 177-184, (2007). DOI: https://doi.org/10.1560/ijc.47.2.177
  • [49] Kartal, Z., Sayın, E., “FTIR spectroscopic and thermal study of M(Cyclohexanethiol)2Ni(CN)4•(1,4-dioxane) clathrate (M = Mn, Co, Ni and Cd)”, Journal of Molecular Structure, 994(1-3): 170-178, (2011). DOI: https://doi.org/10.1016/j.molstruc.2011.03.014
  • [50] Kartal, Z., Türk, T., “FT-IR spectroscopic and thermal study of M(1,6-hexanedithiol)Ni(CN)4⋅2(1,4-dioxane) clathrate (M = Mn, Co, Ni and Cd)”, Journal of Molecular Structure, 1014: 74-80, (2012). DOI: https://doi.org/10.1016/j.molstruc.2012.01.031
  • [51] Eckert, S., Miedema, P.S., Quevedo, W., O’Cinneide, B., Fondell, M., Beye, M., Pietzsch, A., Ross, M., Khalil, M., Föhlisch, A., “Molecular structures and protonation state of 2-Mercaptopyridine in aqueous solution”, Chemical Physics Letters, 647: 103-106, (2016). DOI: https://doi.org/10.1016/j.cplett.2016.01.050
  • [52] Do, W.H., Lee, C.J., Kim, D.Y., Jung, M.J., “Adsorption of 2-mercaptopyridine and 4-mercaptopyridine on a silver surfaces investigated by SERS spectroscopy”, Journal of Industrial and Engineering Chemistry, 18(6): 2141-2146, (2012). DOI: https://doi.org/10.1016/j.jiec.2012.06.009
  • [53] Jamroz, M.H., “Vibrational Energy Distribution Analysis VEDA 4”, Warsaw, (2004-2010).
  • [54] Solomons, T.W.G., Fryhle, C.B., Scott, A., “Organic Chemistry”, New York, USA: Wiley, ISBN 10: 1119768195, (2022).
  • [55] Lockwood, D.J., “Raman Spectra of Cadmium Chloride and Cadmium Bromide. In: G.B. Wright (eds) Light Scattering Spectra of Solids”, Springer, Berlin, Heidelberg, (1969). DOI: https://doi:10.1007/978-3-642-87357-7_6
  • [56] Lockwood, D.J., “Lattice vibrations of CdCl2, CdBr2, MnCl2, and CoCl2: infrared and Raman spectra”, Journal of the Optical Society of America, 63: 374-382, (1973). DOI: https://doi.org/10.1364/JOSA.63.000374

Year 2024, Volume: 37 Issue: 4, 2036 - 2060, 01.12.2024

Zeki Kartal , Zarife Sibel Şahin

https://doi.org/10.35378/gujs.1359705

Abstract

References

  • [1] Batten, S.R., Champness, N.R., Chen, X.M., Garcia-Martinez, J., Kitagawa, S., Öhrström, L., O’Keeffe, M., Suh, P., Reedijk, J., “Terminology of metal–organic frameworks and coordination polymers (IUPAC Recommendations 2013)”, Pure and Applied Chemistry, 85(8): 1715-1724, (2013). DOI: https://doi.org/10.1351/PAC-REC-12-11-20
  • [2] Fromm, K., “Coordination polymer networks with s-block metal ions”, Coordination Chemistry Reviews; 252 (8–9): 856-885, (2008). DOI: https://doi.org/10.1016/j.ccr.2007.10.032
  • [3] Yang, Y., Jiang, G., Li, Y.Z., Bai, J., Pan, Y., You, X.Z., “Synthesis, structures and properties of alkaline earth metal benzene-1.4-dioxylacetates with three-dimensional hybrid networks”, Inorganica Chimica Acta, 359(10): 3257-3263, (2006). DOI: https://doi.org/10.1016/j.ica.2006.03.038
  • [4] Adams, E.J., Skrydstrup. T., Lindsay, K.B., “2-Pyridinethiol, Encyclopedia of Reagents for Organic Synthesis”, (2005). DOI: https://doi.org/10.1002/047084289X.rp286
  • [5] Shunmugam, R., Sathyanarayana, D.N., “Raman and polarized infrared spectra of pyridine-2-thione”, Spectrochimica Acta Part A: Molecular Spectroscopy, 40(8):757-761, (1984). DOI: https://doi.org/10.1016/0584-8539(84)80100-2
  • [6] Castiñiras, A., Hiller, W., Strähle, J., Bravo, J., Casas, J., Gayoso, M., Sordo, J., “Methyl- and phenyl-mercury(II) derivatives of 2-mercaptopyridine. Crystal and molecular structure of methyl(pyridine-2-thiolato)mercury(II)”, Journal of the Chemical Society, Dalton Transactions, 9:1945-1948, (1986). DOI: https://doi.org/10.1039/dt9860001945
  • [7] Toma, H.E., Santos, P.S., Mattioli, M.P.D., Oliveira, L.A.A., “Kinetics, electrochemistry and resonance raman spectra of the (2-mercaptopyridine) (edta)ruthenium(III) complex”, Polyhedron, 6(3): 603-611, (1987). DOI: https://doi.org/10.1016/S0277-5387(00)81031-1
  • [8] Baldwin, J.A., Vlčková, B., Andrews, M.P., Butler, S., “Surface-Enhanced Raman Scattering of Mercaptopyridines and Pyrazinamide Incorporated in Silver Colloid−Adsorbate Films”, Langmuir, 13(14):3744-3751, (1997). DOI: https://doi.org/10.1021/la960719d
  • [9] Pang, Y.S., Hwang, H.J., Kim, M.S., “Adsorption of 2-mercaptopyridine and 2-mercaptopyrimidine on a silver colloidal surface investigated by Raman spectroscopy”, Journal of Molecular Structure, 441(1): 63-76, (1998). DOI: https://doi.org/10.1016/s0022-2860(97)00280-9
  • [10] Zhang, H.L., Evans, S.D., Henderson, J.R., Miles, R.E., Shen, T.H., “Spectroscopic Characterization of Gold Nanoparticles Passivated by Mercaptopyridine and Mercaptopyrimidine Derivatives”, The Journal of Physical Chemistry B, 107(25): 6087-6095, (2003). DOI: https://doi.org/ 10.1002/Adma.200390124
  • [11] Ozturk, I.I., Kourkoumelis, N., Hadjikakou, S.K., Manos, M.J., Tasiopoulos, A.J., Butler, I.S., Balzarini, J., Hadjiliadis, N., “Interaction of antimony(III) chloride with thiourea, 2-mercapto-5-methyl-benzimidazole, 3-methyl-2-mercaptobenzothiazole, 2-mercaptopyrimidine, and 2-mercaptopyridine”, Journal of Coordination Chemistry, 64(22): 3859-3871, (2011). DOI: https://doi.org/10.1080/00958972.2011.633603
  • [12] Do, W.H., Lee, C.J., Kim, D.Y., Jung, M.J., “Adsorption of 2-mercaptopyridine and 4-mercaptopyridine on a silver surfaces investigated by SERS spectroscopy”, Journal of Industrial and Engineering Chemistry, 18(6): 2141-2146, (2012). DOI: https://doi.org/10.1016/j.jiec.2012.06.009
  • [13] Naktode, K., Reddy, T.D.N., Nayek, H.P., Mallik, B.S., Panda, T.K., “Heavier group 2 metal complexes with a flexible scorpionate ligand based on 2-mercaptopyridine”, Royal Society of Chemistry Advances, 5(63): 51413-51420, (2015). DOI: https://doi.org/10.1039/C5RA04696C
  • [14] Ramsay, D.A., “The Vibration Spectrum and Molecular Configuration of 1,4-dioxane”. Proceedings of the Royal Society of London A, 190: 562-574, (1947). DOI: https://doi.org/10.1098/rspa.1947.0097
  • [15] Malherbe, F.E., Bernstein, H.J., “The Infrared and Raman Spectra of p-Dioxane”, Journal of the American Chemical Society, 74(17): 4408-4410, (1952). DOI: https://doi.org/10.1021/ja01137a051
  • [16] Snyder, R.G., Zerbi, G., “Vibrational analysis of ten simple aliphatic ethers: Spectra, assignments, valence force field and molecular conformations”, Spectrochimica Acta Part A: Molecular Spectroscopy, 23(2): 391-437, (1967). DOI: https://doi.org/10.1016/0584-8539(67)80241-1
  • [17] Ellestad, O.H., Klaboe, P., Hagen, G., “The vibrational spectra of 1,4-dioxan-do and 1,4- dioxan-d8”, Spectrochimica Acta, 27A: 1025-1048, (1971). DOI: https://doi.org/10.1016/0584-8539(71)80186-1
  • [18] Karayannis, N.M., Mikulski, C.M., Speca, A.N., Cronin, J.T., Pytlewski, L.L., “p-Dioxane, p-thioxane, and 1,2-dimethoxyethane complexes with transition metal perchlorates”, Inorganic Chemistry, 11(10): 2330-2335, (1972). DOI: https://doi.org/10.1021/ic50116a008
  • [19] Shimanouchi, T., “Tables of molecular vibrational frequencies consolidated volume II”, Journal of Physical and Chemical Reference Data., 6(3): 993-1102, (1977). DOI: https://doi.org/10.1063/1.555560
  • [20] Schwarz, W., Schmidt, A., Binder, G.E., “1,4-Dioxan•H2O•SbCl5; Vibrational Spectra, Crystal and Molecular Structure”, Zeitschrift für Naturforschung B, 33(2): 136-139, (1978). DOI: https://doi.org/10.1515/znb-1978-0202
  • [21] Dempster, A.B., Uslu, H., “Infrared spectra and stability of Hofmann-type dioxane clathrates”, Spectrochimica Acta Part A: Molecular Spectroscopy, 34(1): 71-75, (1978). DOI: https://doi.org/10.1016/0584-8539(78)80188-3
  • [22] Den, H.M., Driessen, W.L., “Ethers as ligands, Part IV, Metal(II) 1,4-dioxane solvates”, Inorganica Chimica Acta, 39:43-46, (1980). DOI: https://doi.org/10.1016/s0020-1693(00)93631-4
  • [23] Parvez, M., Pajerski, A.D., Richey, H.G., “(Dioxane)dineopentylmagnesium: a polymeric structure”, Acta Crystallographica Section C Crystal Structure Communications, 44(7): 1212-1215, (1998). DOI: https://doi.org/10.1107/s0108270188003099
  • [24] Edelmann, F.T., Pauer, F., Wedler, M., Stalke, D., “Preparation and structural characterization of dioxane-coordinated alkali metal bis(trimethylsilyl)amides”, Inorganic Chemistry, 31(20): 4143-4146, (1992). DOI: https://doi.org/10.1021/ic00046a028
  • [25] Parlak, C., Alver, Ö., “Spectroscopic investigations of 1,4-dioxane adsorbed on bentonite from Anatolia”, Anadolu University Journal of Science and Technology A - Applied Sciences and Engineering, 17(2): 273-277, (2016). DOI: https://doi.org/10.18038/btda,87236
  • [26] Borowski, P., Gac, W., Pulay, P., Wolinski, K., “The vibrational spectrum of 1,4-dioxane in aqueous solution – theory and experiment”, New Journal of Chemistry, 40(9): 7663-7670, (2016). DOI: https://doi.org/10.1039/c6nj01198e
  • [27] Kartal, Z., Yavuz, A., “The synthesis and the spectroscopic, thermal, and structural properties of the M2[(fumarate)Ni(CN)4]•2(1,4-Dioxane) clathrate (M = Co, Ni, Cd and Hg)”, Journal of Molecular Structure, 1155: 171-183, (2018). DOI: https://doi.org/10.1016/j.molstruc.2017.10.107
  • [28] Lockwood, D.J., Bertrand, D., Carrara, P., Mischler, G., Billerey, D., Terrier, C., “Raman spectrum of NiCl2”, Journal of Physics C: Solid State Physics, 11(17): 3615-3620, (1979). DOI: https://doi.org/10.1088/0022-3719/12/17/031
  • [29] Agulló-Rueda, F., Calleja, J.M., Martini, M., Spinolo, G., Cariati, F., “Raman and infrared spectra of transition metal halide hexahydrates”, Journal of Raman Spectroscopy, 18(7): 485-491, (1987). DOI: https://doi.org/10.1002/jrs.1250180707
  • [30] Lide, D.R., “CRC Handbook of Chemistry and Physics”, 90th ed, Boca Raton, Florida, USA: CRC Press, ISBN 978-1-4200-9084-0, (2009).
  • [31] Seidell, A., “Solubilities of Inorganic and Organic Compounds: A Compilation of Quantitave Solubility Data From the Periodical Literature; Volume 1”, Legare Street Press, ISBN-10: 1015948987, (2022).
  • [32] Greenwood, N.N., Earnshaw, A., “Chemistry of the Elements”, 2nd ed, Butterworth-Heinemann, Oxford, UK: ISBN: 9780750633659. (1997).
  • [33] Wells, A.F., “Structural Inorganic Chemistry”, 4th ed, Oxford University Press, Oxford, UK: ISBN: 0198553544, (1975).
  • [34] Smith, M.B., March, J., “March’s Advanced Organic Chemistry: Reactions, Mechanisms, and Structure”. 6th ed., Wiley, New York, USA: ISBN-10: 0471720917, (2007).
  • [35] Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Montgomery, Jr.J.A., Vreven, T., Kudin, K.N., Burant, J.C., Millam, J.M., Iyengar, S.S., Tomasi, J., Barone, V., Mennucci, B., Cossi, M., Scalmani, G., Rega, N., Petersson, G.A., Nakatsuji, H., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Klene, M., Li, X., Knox, J.E., Hratchian, H. P., Cross, J.B., Bakken, V., Adamo, C., Jaramillo, J., Dapprich, S., Daniels, A.D., Strain, M.C., Farkas, O., Malick, D.K., Rabuck, A.D., Raghavachari, K., Foresman, J.B., Ortiz, J.V., Cui, Q., Baboul, A.G., Clifford, S., Cioslowski, J., Stefanov, B.B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., Martin, R.L., Fox, D.J., Keith, T., Al-Laham, M.A., Peng, C.Y., Nanayakkara, A., Challacombe, M., Gill, P.M.W., Johnson, B., Chen, W., Wong, M.W., Gonzalez, C., Pople, J.A., Gaussian 03 Revision D.01. Gaussian, Inc., Wallingford CT, (2004).
  • [36] Young, D.C., “Computational chemistry: a practical guide for applying techniques to real-world problems (electronics)”, New York, USA: Wiley, ISBN:  0-471-33368-9, (2001).
  • [37] Dennington, R., Keith, T., Millam, J., Gauss View, Version 4.1.2. Semichem Inc., Shawnee Mission (2007).
  • [38] Sheldrick, G.M., “A short history of SHELX”, Acta Crystallographica, A64: 112-122, (2008). DOI: https://doi.org/10.1107/S0108767307043930
  • [39] Farrugia, L.J., “WinGX and ORTEP for Windows: an update”, Journal of Applied Crystallography, 45: 849-854, (2012). DOI: https://doi.org/10.1107/S0021889812029111
  • [40] Macrae, C.F., Bruno, I.J., Chisholm, J.A., Edgington, P., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J., Wood, P.A., “Mercury CSD 2.0 – New features for the visualization and investigation of crystal structures”, Journal of Applied Crystallography, 41: 466-470, (2008). DOI: https://doi.org/10.1107/S0021889807067908
  • [41] Sickerman, N.S., Park, Y.J., Ng, G.K.Y., Bates, J.E. Hilkert, M., Ziller, J.W., Furche, F., Borovik, A.S., “Synthesis, structure, and physical properties for a series of trigonal bipyramidal M(II)-Cl complexes with intramolecular hydrogen bonds”, Dalton Transactions, 41(15): 4358-4364, (2012). DOI: https://doi.org/10.1039/c2dt12244h
  • [42] Gusev, A.N., Shul’gin, V.F., Ryush, I.O., Hasegawa, M., Kiskin, M.A., Efimov, N.N., Konstantin, A., Lyssenko, A., Eremenko, I.L., Linert, W., “Copper(II), Nickel(II), and Cobalt(II)/(III) Self-Assembled Polynuclear Complexes of Bis[(pyridin-2-yl)-1,2,4-triazol-3-yl]]methane”, European Journal of Inorganic Chemistry, 3: 704-712, (2017). DOI: https://doi.org/10.1002/ejic.201601107
  • [43] Paes, L.W.C., Suárez, J.A., Márquez, A.M., Sanz, J.F., “First-principles study of nickel complex with 1,3-dithiole-2-thione-4,5-dithiolate ligands as model photosensitizers”, Theoretical Chemistry Accounts, 136(6): 1-9, (2017). DOI: https://doi.org/10.1007/s00214-017-2098-7
  • [44] Hakimi, M., Mardani, Z., Moeini, K., Fernandes, M.A., “Coordination geometries and crystal structures of cadmium(II) complexes with a new amino alcohol (NN′O) ligand”, Journal of Coordination Chemistry, 65(13): 2221-2233, (2012). DOI: https://doi.org/10.1080/00958972.2012.690145
  • [45] Kawasaki, T., Kitazawa, T., “Synthesis and Crystal Structures of Cadmium(II) Cyanide with Branched-Butoxyethanol”, Crystals, 8(5): 221/1-221/10, (2018). https://doi.org/10.3390/cryst8050221
  • [46] BelhajSalah, S., Abdelbaky, M.S.M., García-Granda, S., Essalah, K., Ben Nasr, C., Mrad, M.L., “Crystal structure, Hirshfeld surfaces computational study and physicochemical characterization of the hybrid material (C7H10N)2[SnCl6]•H2O”, Journal of Molecular Structure, 1152: 276-286, (2018). DOI: https://doi.org/10.1016/j.molstruc.2017.09.098
  • [47] Jellali, A., Elleuch, S., Hamdi, B., Zouari, R., “Experimental and theoretical investigations of the molecular structure, the spectroscopic properties and TD-DFT analysis of a new semiconductor hybrid based iron (III)”, Journal of Saudi Chemical Society, 23(5): 600-611, (2019). DOI: https://doi.org/10.1016/j.jscs.2018.10.006
  • [48] Zhang, W., Schmid, T., Yeo, B.S., Zenobi, R., “Tip-enhanced Raman spectroscopy reveals rich nanoscale adsorption chemistry of 2-mercaptopyridine on Ag”, Israel Journal of Chemistry, 47(2): 177-184, (2007). DOI: https://doi.org/10.1560/ijc.47.2.177
  • [49] Kartal, Z., Sayın, E., “FTIR spectroscopic and thermal study of M(Cyclohexanethiol)2Ni(CN)4•(1,4-dioxane) clathrate (M = Mn, Co, Ni and Cd)”, Journal of Molecular Structure, 994(1-3): 170-178, (2011). DOI: https://doi.org/10.1016/j.molstruc.2011.03.014
  • [50] Kartal, Z., Türk, T., “FT-IR spectroscopic and thermal study of M(1,6-hexanedithiol)Ni(CN)4⋅2(1,4-dioxane) clathrate (M = Mn, Co, Ni and Cd)”, Journal of Molecular Structure, 1014: 74-80, (2012). DOI: https://doi.org/10.1016/j.molstruc.2012.01.031
  • [51] Eckert, S., Miedema, P.S., Quevedo, W., O’Cinneide, B., Fondell, M., Beye, M., Pietzsch, A., Ross, M., Khalil, M., Föhlisch, A., “Molecular structures and protonation state of 2-Mercaptopyridine in aqueous solution”, Chemical Physics Letters, 647: 103-106, (2016). DOI: https://doi.org/10.1016/j.cplett.2016.01.050
  • [52] Do, W.H., Lee, C.J., Kim, D.Y., Jung, M.J., “Adsorption of 2-mercaptopyridine and 4-mercaptopyridine on a silver surfaces investigated by SERS spectroscopy”, Journal of Industrial and Engineering Chemistry, 18(6): 2141-2146, (2012). DOI: https://doi.org/10.1016/j.jiec.2012.06.009
  • [53] Jamroz, M.H., “Vibrational Energy Distribution Analysis VEDA 4”, Warsaw, (2004-2010).
  • [54] Solomons, T.W.G., Fryhle, C.B., Scott, A., “Organic Chemistry”, New York, USA: Wiley, ISBN 10: 1119768195, (2022).
  • [55] Lockwood, D.J., “Raman Spectra of Cadmium Chloride and Cadmium Bromide. In: G.B. Wright (eds) Light Scattering Spectra of Solids”, Springer, Berlin, Heidelberg, (1969). DOI: https://doi:10.1007/978-3-642-87357-7_6
  • [56] Lockwood, D.J., “Lattice vibrations of CdCl2, CdBr2, MnCl2, and CoCl2: infrared and Raman spectra”, Journal of the Optical Society of America, 63: 374-382, (1973). DOI: https://doi.org/10.1364/JOSA.63.000374
There are 56 citations in total.

Details

Primary Language English
Subjects Condensed Matter Modelling and Density Functional Theory, Molecular Imaging, Crystallography, Computational Chemistry
Journal Section Physics
Authors

Zeki Kartal 0000-0001-9739-0858

Zarife Sibel Şahin 0000-0003-2745-7871

Early Pub Date August 8, 2024
Publication Date December 1, 2024
Published in Issue Year 2024 Volume: 37 Issue: 4

Cite

APA Kartal, Z., & Şahin, Z. S. (2024). Synthesis, Characterization, Spectral Analysis and Molecular Simulation Studies of compounds formed by 2-mercaptopyridine and 1,4-dioxane ligands with some metal(II) chlorides. Gazi University Journal of Science, 37(4), 2036-2060. https://doi.org/10.35378/gujs.1359705
AMA Kartal Z, Şahin ZS. Synthesis, Characterization, Spectral Analysis and Molecular Simulation Studies of compounds formed by 2-mercaptopyridine and 1,4-dioxane ligands with some metal(II) chlorides. Gazi University Journal of Science. December 2024;37(4):2036-2060. doi:10.35378/gujs.1359705
Chicago Kartal, Zeki, and Zarife Sibel Şahin. “Synthesis, Characterization, Spectral Analysis and Molecular Simulation Studies of Compounds Formed by 2-Mercaptopyridine and 1,4-Dioxane Ligands With Some metal(II) Chlorides”. Gazi University Journal of Science 37, no. 4 (December 2024): 2036-60. https://doi.org/10.35378/gujs.1359705.
EndNote Kartal Z, Şahin ZS (December 1, 2024) Synthesis, Characterization, Spectral Analysis and Molecular Simulation Studies of compounds formed by 2-mercaptopyridine and 1,4-dioxane ligands with some metal(II) chlorides. Gazi University Journal of Science 37 4 2036–2060.
IEEE Z. Kartal and Z. S. Şahin, “Synthesis, Characterization, Spectral Analysis and Molecular Simulation Studies of compounds formed by 2-mercaptopyridine and 1,4-dioxane ligands with some metal(II) chlorides”, Gazi University Journal of Science, vol. 37, no. 4, pp. 2036–2060, 2024, doi: 10.35378/gujs.1359705.
ISNAD Kartal, Zeki - Şahin, Zarife Sibel. “Synthesis, Characterization, Spectral Analysis and Molecular Simulation Studies of Compounds Formed by 2-Mercaptopyridine and 1,4-Dioxane Ligands With Some metal(II) Chlorides”. Gazi University Journal of Science 37/4 (December 2024), 2036-2060. https://doi.org/10.35378/gujs.1359705.
JAMA Kartal Z, Şahin ZS. Synthesis, Characterization, Spectral Analysis and Molecular Simulation Studies of compounds formed by 2-mercaptopyridine and 1,4-dioxane ligands with some metal(II) chlorides. Gazi University Journal of Science. 2024;37:2036–2060.
MLA Kartal, Zeki and Zarife Sibel Şahin. “Synthesis, Characterization, Spectral Analysis and Molecular Simulation Studies of Compounds Formed by 2-Mercaptopyridine and 1,4-Dioxane Ligands With Some metal(II) Chlorides”. Gazi University Journal of Science, vol. 37, no. 4, 2024, pp. 2036-60, doi:10.35378/gujs.1359705.
Vancouver Kartal Z, Şahin ZS. Synthesis, Characterization, Spectral Analysis and Molecular Simulation Studies of compounds formed by 2-mercaptopyridine and 1,4-dioxane ligands with some metal(II) chlorides. Gazi University Journal of Science. 2024;37(4):2036-60.