تهیه، شناسایی و تعیین ساختار بلوری پلیمر کئوردیناسیونی جدید از فلز روی دارای لیگاند N-(4-پیریدیل)ایزونیکوتین‌آمید

نوع مقاله : مقاله پژوهشی

نویسندگان

دانشگاه فردوسی مشهد

چکیده

در این پژوهش، پلیمر کئوردیناسیونی جدید از واکنش کلرید روی و ترکیب کربوکسامید LNPI –N (4-پیریدیل)ایزونیکوتین آمید تهیه شد و با استفاده از طیف­سنجی تبدیل فوریه فروسرخ (FT-IR)، تجزیه­ی عنصری (CHN)، میکروسکوپ الکترونی روبشی (SEM) و پراش پرتو ایکس نمونه‌ی تک­بلور شناسایی گردید. نتایج نشان داد که ترکیب [ZnCl2(LNPI)]n با ساختار پلیمر یک بعدی به صورت زنجیره­ی زیگزاگی در سیستم بلوری راستگوشی (با گروه فضایی Pca21 متبلور شده است. بررسی برهم­کنش­های بین­مولکولی و تحلیل سطح هرشفلد در ساختار بلوری ترکیب نشان داد که پیوند هیدروژنی Zn-Cl∙∙∙H-N نقش موثری در پایداری زنجیرهای پلیمری در ساختار انباشته‌ی بلوری دارد. به منظور درک بهتر ساختار مولکولی و ویژگی­های الکترونی لیگاند و کمپلکس، محاسبات بر پایه نظریه تابعی چگالی (DFT) نیز انجام شد.     

کلیدواژه‌ها

عنوان مقاله [English]

Synthesis, characterization and crystal structure determination of new coordination polymer of zinc(II) containing N-(4-pyridyl)isonocotinamide ligand

نویسندگان [English]

  • Abolghasempour
  • Salimi
  • Nakhaei Pour
چکیده [English]

In this study, new coordination polymer was synthesized by the reaction of ZnCl2 and LNPI carboxamide, (N-(4-pyridyl)isonicotinamide) as well as characterized by FT-IR spectroscopy, elemental analysis (CHN), scanning electron microscope (SEM) and single-crystal X-ray diffraction analysis. The results revealed that the compound [ZnCl2 (LNPI)]n, as a one-dimensional zig-zag polymeric chain, was crystallized in “orthorhombic” crystalline system with the space group Pca21. The study of intermolecular interactions and hirshfeld surface analysis showed that the Zn-Cl∙∙∙H-N hydrogen bond plays an important role in the stability of the polymeric chains in the crystal packing structure. To get more insight about molecular structure and electronic properties of ligand and complex structures, theoretical studies using density functional theory (DFT) method were performed.

کلیدواژه‌ها [English]

  • Coordination polymer
  • carboxamide
  • single crystal
  • hydrogen bond
  • theoretical study

مراجع

  1. [1] Desiraju G. R., "Crystal Engineering: A Holistic View", Angew. Chem. Int. Ed., 46 (2007) 8342-8356. [DOI:10.1002/anie.200700534]
  2. [1] Desiraju G. R., "Crystal Engineering: A Holistic View", Angew. Chem. Int. Ed., 46 (2007) 8342-8356. [DOI:10.1002/anie.200700534]
  3. [2] Desiraju G. R., "Crystal Engineering: From Molecule to Crystal", J. Am. Chem. Soc., 135 (2013) 9952-9967. [DOI:10.1021/ja403264c]
  4. [2] Desiraju G. R., "Crystal Engineering: From Molecule to Crystal", J. Am. Chem. Soc., 135 (2013) 9952-9967. [DOI:10.1021/ja403264c]
  5. [3] Althagbi H. I., Lane J. R., Saunders G. C., Webb S. J., "Engineering polar crystal structures by p-p stacking of N-perfluoroarylbenzimidazoles" , J. Fluor. Chem., 166 (2014) 88-95. [DOI:10.1016/j.jfluchem.2014.07.024]
  6. [3] Althagbi H. I., Lane J. R., Saunders G. C., Webb S. J., "Engineering polar crystal structures by p-p stacking of N-perfluoroarylbenzimidazoles" , J. Fluor. Chem., 166 (2014) 88-95. [DOI:10.1016/j.jfluchem.2014.07.024]
  7. [4] Braga D., Desiraju, G. R., Miller, J. S., Orpen, A. G., Price, S. L.," Innovation in crystal engineering", CrystEngComm, 4, (2002) 500-509. [DOI:10.1039/B207466B]
  8. [4] Braga D., Desiraju, G. R., Miller, J. S., Orpen, A. G., Price, S. L.," Innovation in crystal engineering", CrystEngComm, 4, (2002) 500-509. [DOI:10.1039/B207466B]
  9. [5] Lee B., "Developments in inorganic crystal engineering" , Chem. Soc. Rev., 33 (2004) 476-489. [DOI:10.1039/b313412c]
  10. [5] Lee B., "Developments in inorganic crystal engineering" , Chem. Soc. Rev., 33 (2004) 476-489. [DOI:10.1039/b313412c]
  11. [6] Moulton B., Zaworotko M., " From Molecules to Crystal Engineering: Supramolecular Isomerism and Polymorphism in Network Solids", Chem. Rev., 101 (2001)1629 -1658. [DOI:10.1021/cr9900432]
  12. [6] Moulton B., Zaworotko M., " From Molecules to Crystal Engineering: Supramolecular Isomerism and Polymorphism in Network Solids", Chem. Rev., 101 (2001)1629 -1658. [DOI:10.1021/cr9900432]
  13. [7] Braga D., Grepioni F., "Making crystals from crystals: a green route to crystal engineering and polymorphism ", Chem. Commun., 29 )2005) 3635-3645. [DOI:10.1039/b504668h]
  14. [7] Braga D., Grepioni F., "Making crystals from crystals: a green route to crystal engineering and polymorphism ", Chem. Commun., 29 )2005) 3635-3645. [DOI:10.1039/b504668h]
  15. [8] Rahmani, M., Salimi, A., Mohammadzadeh, S., Sparkes, H. A., "The supramolecular effect of aromaticity on the crystal packing of furan/thiophene carboxamide compounds ", CrystEngComm, 18 (2016) 8953-8960. [DOI:10.1039/C6CE01945E]
  16. [8] Rahmani, M., Salimi, A., Mohammadzadeh, S., Sparkes, H. A., "The supramolecular effect of aromaticity on the crystal packing of furan/thiophene carboxamide compounds ", CrystEngComm, 18 (2016) 8953-8960. [DOI:10.1039/C6CE01945E]
  17. [9] Azadbakht A., Abbasi A. R., Derikvand Z., Morsali A.,"Characterization of crystal structure of 4-(4H-1,2,4-Triazol-4-yl) phenol prepared by hydrothermal method", Iran J. Cryst. Miner., 24, (2016), 581-586 [DOI:10.1107/S2053273316094043]
  18. [9] Azadbakht A., Abbasi A. R., Derikvand Z., Morsali A.,"Characterization of crystal structure of 4-(4H-1,2,4-Triazol-4-yl) phenol prepared by hydrothermal method", Iran J. Cryst. Miner., 24, (2016), 581-586 [DOI:10.1107/S2053273316094043]
  19. [10] Mukherjee A., "Building upon Supramolecular Synthons: Some Aspects of Crystal Engineerings", Cryst. Growth Des., 15 (2015) 3076−3085. [DOI:10.1021/acs.cgd.5b00242]
  20. [10] Mukherjee A., "Building upon Supramolecular Synthons: Some Aspects of Crystal Engineerings", Cryst. Growth Des., 15 (2015) 3076−3085. [DOI:10.1021/acs.cgd.5b00242]
  21. [11] Desiraju G. R., "Reflections on the Hydrogen Bond in Crystal Engineering", Cryst. Growth Des., 11 (2011) 896-898. [DOI:10.1021/cg200100m]
  22. [11] Desiraju G. R., "Reflections on the Hydrogen Bond in Crystal Engineering", Cryst. Growth Des., 11 (2011) 896-898. [DOI:10.1021/cg200100m]
  23. [12] Mukherjee G., Biradha K., "Dynamic Layered Coordination Polymer: Adsorption and Separation of Aromatics and I2 by Single Crystals", Cryst. Growth Des., 14 (2014) 3696−3699 [DOI:10.1021/cg500658x]
  24. [12] Mukherjee G., Biradha K., "Dynamic Layered Coordination Polymer: Adsorption and Separation of Aromatics and I2 by Single Crystals", Cryst. Growth Des., 14 (2014) 3696−3699 [DOI:10.1021/cg500658x]
  25. [13] Blake A. J., Champness N. R., Hubberstey P., Li W.S., Withersby M. A., Schroder M., "Inorganic crystal engineering usingself-assembly of tailored building-blocks" Coord. Chem. Rev., 183 (1999) 117-138. [DOI:10.1016/S0010-8545(98)00173-8]
  26. [13] Blake A. J., Champness N. R., Hubberstey P., Li W.S., Withersby M. A., Schroder M., "Inorganic crystal engineering usingself-assembly of tailored building-blocks" Coord. Chem. Rev., 183 (1999) 117-138. [DOI:10.1016/S0010-8545(98)00173-8]
  27. [14] Mukhejee G., Biradha K., "Crystal Engineering Studies with Monocarboxamidoalkanes Having C- or N-Terminal Pyridine and Their Coordination Complexes" Cryst. Growth Des., 11 (2011) 5649-5658. [DOI:10.1021/cg2012028]
  28. [14] Mukhejee G., Biradha K., "Crystal Engineering Studies with Monocarboxamidoalkanes Having C- or N-Terminal Pyridine and Their Coordination Complexes" Cryst. Growth Des., 11 (2011) 5649-5658. [DOI:10.1021/cg2012028]
  29. [15] Biradha K., "Crystal engineering: from weak hydrogen bonds to co-ordination bonds", CrystEngComm, 5 (2003) 374-384. [DOI:10.1039/b309903b]
  30. [15] Biradha K., "Crystal engineering: from weak hydrogen bonds to co-ordination bonds", CrystEngComm, 5 (2003) 374-384. [DOI:10.1039/b309903b]
  31. [16] Braga D., Maini L., Polito M., Grepioni F.,"Hydrogen bonding interactions between ions: A powerful tool in molecular crystal engineering", Struct. Bond., 111 (2004) 1-32. [DOI:10.1007/b14139]
  32. [16] Braga D., Maini L., Polito M., Grepioni F.,"Hydrogen bonding interactions between ions: A powerful tool in molecular crystal engineering", Struct. Bond., 111 (2004) 1-32. [DOI:10.1007/b14139]
  33. [17] Steed J. W., Atwood J. L., "Supramolecular Chemistry", Wiley, Chichester, U. K., 2000
  34. [17] Steed J. W., Atwood J. L., "Supramolecular Chemistry", Wiley, Chichester, U. K., 2000
  35. [18] Amani A., Derikvand Z., Azadbakht A., Notash B., "Synthesis, characterization and crystal
  36. [18] Amani A., Derikvand Z., Azadbakht A., Notash B., "Synthesis, characterization and crystal
  37. structure of a co-crystal compound including 4,4'-bipyridine, 3-nithrophthalic acid (in persian)" Iran
  38. structure of a co-crystal compound including 4,4'-bipyridine, 3-nithrophthalic acid (in persian)" Iran
  39. J. Cryst. Miner., 25 (2017) 207-212. [DOI:10.1159/000490446]
  40. J. Cryst. Miner., 25 (2017) 207-212. [DOI:10.1159/000490446]
  41. [19] Arunan E., Desiraju G. R., Klein R. A., Sadlej J., Scheiner S., Alkorta I., Clary D. C., Crabtree R. H., Dannenberg J., Hobza P., Kjaergaard H. G., Legon A. C., Mennucci B., Nesbitt D. "Definition of the hydrogen bond (IUPAC recommendations 2011) ", Pure Appl. Chem., 83 (2011) 1637-1641. [DOI:10.1351/PAC-REC-10-01-02]
  42. [19] Arunan E., Desiraju G. R., Klein R. A., Sadlej J., Scheiner S., Alkorta I., Clary D. C., Crabtree R. H., Dannenberg J., Hobza P., Kjaergaard H. G., Legon A. C., Mennucci B., Nesbitt D. "Definition of the hydrogen bond (IUPAC recommendations 2011) ", Pure Appl. Chem., 83 (2011) 1637-1641. [DOI:10.1351/PAC-REC-10-01-02]
  43. [20] Kitagawa S., Kitaura R., Noro S., "Functional Porous Coordination Polymers" Angew. Chem. Int. Ed., 43 (2004) 2334 -2375. [DOI:10.1002/anie.200300610]
  44. [20] Kitagawa S., Kitaura R., Noro S., "Functional Porous Coordination Polymers" Angew. Chem. Int. Ed., 43 (2004) 2334 -2375. [DOI:10.1002/anie.200300610]
  45. [21] Kubota Y., Takata M., Matsuda R., " Direct Observation of Hydrogen Molecules Adsorbed onto a Microporous Coordination Polymer" ., Angew. Chem. Int. Ed., 44 (2005) 920 -923. [DOI:10.1002/anie.200461895]
  46. [21] Kubota Y., Takata M., Matsuda R., " Direct Observation of Hydrogen Molecules Adsorbed onto a Microporous Coordination Polymer" ., Angew. Chem. Int. Ed., 44 (2005) 920 -923. [DOI:10.1002/anie.200461895]
  47. [22] Khavasi H. R., Mir Mohammad Sadegh B.,"Effect of robust π-π stacking synthon on the
  48. [22] Khavasi H. R., Mir Mohammad Sadegh B.,"Effect of robust π-π stacking synthon on the
  49. formation of mercury coordination compounds; an unusual pseudo-square planar geometry", Dalton
  50. formation of mercury coordination compounds; an unusual pseudo-square planar geometry", Dalton
  51. Trans., 43 (2014) 5564-5573. [DOI:10.1039/C3DT53220H]
  52. Trans., 43 (2014) 5564-5573. [DOI:10.1039/C3DT53220H]
  53. [23] Hadad zade H., Rezvani A. R., "Crystal Structure of Trans- [bis(2,5-dichlorophenylcyanamido ) {N,N′-propanediylbis(2,3-butadien-2-imine-3-oxime)} Cobalt(III)], trans-[Co((DO)(DOH)pn)(2,5-Cl2pcyd)2] ", Iran J. Cryst. Miner., 12 (2004) 273-284.
  54. [23] Hadad zade H., Rezvani A. R., "Crystal Structure of Trans- [bis(2,5-dichlorophenylcyanamido ) {N,N′-propanediylbis(2,3-butadien-2-imine-3-oxime)} Cobalt(III)], trans-[Co((DO)(DOH)pn)(2,5-Cl2pcyd)2] ", Iran J. Cryst. Miner., 12 (2004) 273-284.
  55. [24] Khavasi H. R., Ghanbarpour A. R., Azhdari Tehrani A., "The role of intermolecular interactions involving halogens in the supramolecular architecture of a series of Mn(II) coordination compounds", RSC Adv., 6 (2016) 2422-2430. [DOI:10.1039/C5RA25192C]
  56. [24] Khavasi H. R., Ghanbarpour A. R., Azhdari Tehrani A., "The role of intermolecular interactions involving halogens in the supramolecular architecture of a series of Mn(II) coordination compounds", RSC Adv., 6 (2016) 2422-2430. [DOI:10.1039/C5RA25192C]
  57. [25] Krishna Kumar D., Amilan Jose D., Dastidar P., Das A.,"Nonpolymeric Hydrogelator Derived from N-(4-Pyridyl)isonicotinamide " Langmuir 20 (2004) 10413-10418. [DOI:10.1021/la049097j]
  58. [25] Krishna Kumar D., Amilan Jose D., Dastidar P., Das A.,"Nonpolymeric Hydrogelator Derived from N-(4-Pyridyl)isonicotinamide " Langmuir 20 (2004) 10413-10418. [DOI:10.1021/la049097j]
  59. [26] CrysAlisPRO Software system, Version 1.171.39.31c. Rigaku Oxford Diffraction, Rigaku Corporation, Oxford, U. K. 2017.
  60. [26] CrysAlisPRO Software system, Version 1.171.39.31c. Rigaku Oxford Diffraction, Rigaku Corporation, Oxford, U. K. 2017.
  61. [27] Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H., "OLEX2: a complete structure solution, refinement and analysis program" J. Appl. Cryst. 42, (2009) 339-341. [DOI:10.1107/S0021889808042726]
  62. [27] Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H., "OLEX2: a complete structure solution, refinement and analysis program" J. Appl. Cryst. 42, (2009) 339-341. [DOI:10.1107/S0021889808042726]
  63. [28] Sheldrick, G.M., " A short history of SHELX" Acta Cryst. A64, (2008) 112-122. [DOI:10.1107/S0108767307043930]
  64. [28] Sheldrick, G.M., " A short history of SHELX" Acta Cryst. A64, (2008) 112-122. [DOI:10.1107/S0108767307043930]
  65. [29] Sheldrick, G.M., "Crystal structure refinement with SHELXL" Acta Cryst. C71, (2015) 3-8. [DOI:10.1107/S2053229614024218]
  66. [29] Sheldrick, G.M., "Crystal structure refinement with SHELXL" Acta Cryst. C71, (2015) 3-8. [DOI:10.1107/S2053229614024218]
  67. [30] Turner M. J., McKinnon J. J., Wolff S. K., Grimwood D. J., Spackman P. R., Jayatilaka D.,
  68. [30] Turner M. J., McKinnon J. J., Wolff S. K., Grimwood D. J., Spackman P. R., Jayatilaka D.,
  69. Spackman M. A., CrystalExplorer 17, University of Western Australia, 2017.
  70. Spackman M. A., CrystalExplorer 17, University of Western Australia, 2017.
  71. [31] Frisch, M. J. Gaussian 09, Revision A.1; Gaussian, Inc., Wallingford, CT, 2004.
  72. [31] Frisch, M. J. Gaussian 09, Revision A.1; Gaussian, Inc., Wallingford, CT, 2004.
  73. [32] Alizadeh M.H., Salimi A.R., " Density functional theory and Hartree-Fock studies: Geometry, vibrationalfrequencies and electronic properties of Anderson-type heteropolyanion,[XM6O24]n− (X=TeVI, IVII and M= Mo, W) and [SbVW6O24]7−", Spectrochim. Acta 65A (2006) 1104-1111. [DOI:10.1016/j.saa.2006.02.011]
  74. [32] Alizadeh M.H., Salimi A.R., " Density functional theory and Hartree-Fock studies: Geometry, vibrationalfrequencies and electronic properties of Anderson-type heteropolyanion,[XM6O24]n− (X=TeVI, IVII and M= Mo, W) and [SbVW6O24]7−", Spectrochim. Acta 65A (2006) 1104-1111. [DOI:10.1016/j.saa.2006.02.011]
  75. [33] Salehi H., Nazari H.," Calculation of electronic and structure properties of the semi-conductor MgSe by using the FP-LAPW method", Iran J. Cryst. Miner., 17 (2009) 489-496.
  76. [33] Salehi H., Nazari H.," Calculation of electronic and structure properties of the semi-conductor MgSe by using the FP-LAPW method", Iran J. Cryst. Miner., 17 (2009) 489-496.
  77. [34] Jarzembska K. N., Hoser A. A., Kaminski R., Madsen A. Ø., Durka K., Wozniak K., "Combined Experimental and Computational Studies of Pyrazinamide and Nicotinamide in the Context of Crystal Engineering and Thermodynamics", Cryst. Growth Des. 14 (2014) 3453-3465. [DOI:10.1021/cg500376z]
  78. [34] Jarzembska K. N., Hoser A. A., Kaminski R., Madsen A. Ø., Durka K., Wozniak K., "Combined Experimental and Computational Studies of Pyrazinamide and Nicotinamide in the Context of Crystal Engineering and Thermodynamics", Cryst. Growth Des. 14 (2014) 3453-3465. [DOI:10.1021/cg500376z]
  79. [35] Notash B., " Synthesis, characterization and crystal structure determination of new coordination polymers of cadmium (II) based on pyridine hydrazide ligands", Iran J. Cryst. Miner., 26 (2019) 1001-1012. [DOI:10.29252/ijcm.26.4.1001]
  80. [35] Notash B., " Synthesis, characterization and crystal structure determination of new coordination polymers of cadmium (II) based on pyridine hydrazide ligands", Iran J. Cryst. Miner., 26 (2019) 1001-1012. [DOI:10.29252/ijcm.26.4.1001]
  81. [36] Karimi Ahmadabad F., Pourayoubi M., Necas M., " Synthesis, crystal structure and Hirshfeld surface analysis of acidic salt [4-methyl phenyl ammonium][(O-phenyl) (hydroxyl) phosphate], [4-CH3-C6H4NH3][(C6H5O)P(O)(O)(OH)]", Iran J. Cryst. Miner., 25 (2017) 199-206.
  82. [36] Karimi Ahmadabad F., Pourayoubi M., Necas M., " Synthesis, crystal structure and Hirshfeld surface analysis of acidic salt [4-methyl phenyl ammonium][(O-phenyl) (hydroxyl) phosphate], [4-CH3-C6H4NH3][(C6H5O)P(O)(O)(OH)]", Iran J. Cryst. Miner., 25 (2017) 199-206.
  83. [37] Samie A., Salimi A., " Orientation-dependent conformational polymorphs in two similar pyridine / pyrazine phenolic esters ", CrystEngComm, 21 (2019), 3721-3730. [DOI:10.1039/C8CE02107D]
  84. [37] Samie A., Salimi A., " Orientation-dependent conformational polymorphs in two similar pyridine / pyrazine phenolic esters ", CrystEngComm, 21 (2019), 3721-3730. [DOI:10.1039/C8CE02107D]
  85. [38] Tanaka, D., Henke, A., Albrecht, K., Moeller, M., Nakagawa, K., Kitagawa, S., & Groll, J., "Rapid preparation of flexible porous coordination polymer nanocrystals with accelerated guest adsorption kinetics". Nature Chemistry, 2(5), (2010) 410-416. [DOI:10.1038/nchem.627]
  86. [38] Tanaka, D., Henke, A., Albrecht, K., Moeller, M., Nakagawa, K., Kitagawa, S., & Groll, J., "Rapid preparation of flexible porous coordination polymer nanocrystals with accelerated guest adsorption kinetics". Nature Chemistry, 2(5), (2010) 410-416. [DOI:10.1038/nchem.627]
  87. [39] Panahi, P., Nouruzi, N., Doustkhah, E., Mohtasham, H., Ahadi, A., Ghiasi-Moaser, A., Rostamniaa A., Mahmoudi G., Khataee A., " O Zirconium based porous coordination polymer (PCP) bearing organocatalytic ligand: a promising dual catalytic center for ultrasonic heterocycle synthesis", Ultrasonics - Sonochemistry 58 (2019) 104653. [DOI:10.1016/j.ultsonch.2019.104653]
  88. [39] Panahi, P., Nouruzi, N., Doustkhah, E., Mohtasham, H., Ahadi, A., Ghiasi-Moaser, A., Rostamniaa A., Mahmoudi G., Khataee A., " O Zirconium based porous coordination polymer (PCP) bearing organocatalytic ligand: a promising dual catalytic center for ultrasonic heterocycle synthesis", Ultrasonics - Sonochemistry 58 (2019) 104653. [DOI:10.1016/j.ultsonch.2019.104653]
  89. [40] Rostami S., Nakhaei Pour A., Salimi A., Abolghasempour A., " Hydrogen adsorption in metal- organic frameworks (MOFs): Effects of adsorbent architecture", Int. J. Hydrog. Energy, 43 (2018) 7072-7080. [DOI:10.1016/j.ijhydene.2018.02.160]
  90. [40] Rostami S., Nakhaei Pour A., Salimi A., Abolghasempour A., " Hydrogen adsorption in metal- organic frameworks (MOFs): Effects of adsorbent architecture", Int. J. Hydrog. Energy, 43 (2018) 7072-7080. [DOI:10.1016/j.ijhydene.2018.02.160]

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  • تاریخ دریافت: 05 اسفند 1398
  • تاریخ بازنگری: 13 فروردین 1399
  • تاریخ پذیرش: 15 اردیبهشت 1399

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