Araştırma Makalesi
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Experimental and Theoretical Analysis of (1E,1'E)-N,N'-(hexane-1,6-diyl)bis(1-(thiophen-2-yl)methanimine) and (1E,1'E)-N,N'-(octane-1,8-diyl)bis(1-(thiophen-2-yl)methanimine) Schiff Base Ligands

Yıl 2019, Cilt: 9 Sayı: 3, 1431 - 1442, 01.09.2019
https://doi.org/10.21597/jist.500254

Öz

The aromatic aldehyde thiophene-2-carbaldehyde, using 1,6-diaminohexane and 1,8-diaminoctane, respectively (1E,1'E)-N,N'-(hexane-1,6-diyl)bis(1-(thiophen-2-yl)methanimine) and (1E,1'E)-N,N'-(octane-1,8-diyl)bis(1-(thiophen-2-yl)methanimine) Schiff base ligands were obtained. The ligands were characterized by fourier transform infrared spectroscopy (FT-IR), 1H- and 13C- nuclear magnetic resonance spectroscopy (1H- and 13C- NMR), mass spectroscopy (LC ESI/MS) methods. The antibacterial activity of the ligands was investigated. In addition, the geometric properties of ligands such as bond lengths, bond angles, dihedral angles, electronic properties, highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energies were calculated by using Gaussian 09w program. Experimental and theoretical spectrum data were compared.

Kaynakça

  • Al-Otaibi JS, Al-Wabli RI, 2015. Vibrational spectroscopic investigation (FT-IR and FT-Raman) using ab initio (HF) and DFT (B3LYP) calculations of 3-ethoxymethyl-1,4-dihydroquinolin-4-one. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 137: 7-15.
  • Alkorta I, Perez JJ, 1996. Molecular polarization potential maps of the nucleic acid bases. International Journal of Quantum Chemistry, 57 (1): 123-135.
  • Altürk S, Avcı D, Tamer Ö, Atalay Y, 2018. 1H–pyrazole–3–carboxylic acid: Experimental and computational study. Journal of Molecular Structure, 1164: 28-36.
  • Casella L, Ibers JA, 1981. Synthesis, Characterization, and Reactivity of Copper(I) and Copper(II) Complexes of N,N'-Bis(3-(2-Thenylideneimino)Propyl)Piperazine (Tipp) and N,N'-Bis(3-(2-Thenylamino)Propyl)Piperazine (Tapp). Crystal Structure of [Cu(Tapp)][Clo4]2. Inorganic Chemistry, 20 (8): 2438-2448.
  • Dineshkumar S, Muthusamy A, 2016. Synthesis and Spectral Characterization of Cross Linked Rigid Structured Schiff Base Polymers: Effect of Substituent Position Changes on Optical, Electrical, and Thermal Properties. Polymer-Plastics Technology and Engineering, 55 (4): 368-378.
  • Fedorova EV, Buryakina AV, Vorobieva NM, Baranova NI, 2013. The Vanadium Compounds: Chemistry, Synthesis, Insulinomimetic Properties. Biochemistry (Moscow) Supplement Series B: Biomedical Chemistry, 7 (4): 259-270.
  • Gabr MT, El-Gohary NS, El-Bendary ER, El-Kerdawy MM, Ni N, Shaaban MI, 2015. Synthesis, antimicrobial, antiquorum-sensing and cytotoxic activities of new series of benzothiazole derivatives. Chinese Chemical Letters, 26 (12): 1522-1528.
  • Gadre SR, Shrivastava IH, 1991. Shapes and sizes of molecular anions via topographical analysis of electrostatic potential. The Journal of Chemical Physics, 94 (6): 4384-4390.
  • Gudasi KB, Patil MS, Vadavi RS, Shenoy RV, Patil SA, Nethaji M, 2006. X-ray Crystal Structure of the N-(2-hydroxy-1-naphthalidene)phenylglycine Schiff Base. Synthesis and Characterization of its Transition Metal Complexes. Transition Metal Chemistry, 31 (5): 580-585.
  • Hamada Y, 1997. The development of chelate metal complexes as an organic electroluminescent material. IEEE Transactions on Electron Devices, 44 (8): 1208-1217.
  • Hriday MN, Srivastava RK, Narayan V, S. C, Sachan AK, Shukla VK, Prasad O, Sinha L, 2013. Electronic structure, non-linear properties and vibrational analysis of ortho, meta and para -hydroxybenzaldehyde by density functional theory. Research Journal of Recent Sciences, 2: 150-157.
  • Karakaya C, Dede B, Cicek E, 2016. Novel Metal(II) Complexes with Bidentate Schiff Base Ligand: Synthesis, Spectroscopic Properties and Dye Decolorization Functions. Acta Physica Polonica A, 129 (2): 208-212.
  • Kumar S, Nath Dhar D, N. Saxena P, 2009. Applications of metal complexes of Schiff bases-A review. Journal of scientific and industrial research, 68 (3): 181-187.
  • Luque FJ, Orozco M, Bhadane PK, Gadre SR, 1993. SCRF calculation of the effect of water on the topology of the molecular electrostatic potential. The Journal of Physical Chemistry, 97 (37): 9380-9384.
  • Mihai S, Negoiu M, Bondarev A, 2009. Synthesis, Characterization and Biological Activity of Some Novel Metal Complexes of Schiff Base Derived from p-phenyldiamine and 2-thiophene Carboxaldehyde. Revista de Chimie -Bucharest, 60: 778-782.
  • Murray JS, Sen K. 1996. Molecular Electrostatic Potentials, Concepts and Applications, Elsevier Science, No: 1, pp. 665, Amsterdam-Netherlands
  • Nagy PI, 2013. The syn–anti equilibrium for the COOH group reinvestigated. Theoretical conformation analysis for acetic acid in the gas phase and in solution. Computational and Theoretical Chemistry, 1022: 59-69.
  • Pessoa JC, Etcheverry S, Gambino D, 2015. Vanadium Compounds in Medicine. Coordination Chemistry Reviews, 301-302 (Supplement C): 24-48.
  • Rehder D, 2003. Biological and Medicinal Aspects of Vanadium. Inorganic Chemistry Communications, 6 (5): 604-617.
  • Sreedasyam JS, Sunkari J, Kundha S, Gundapaneni RR, 2013. N,N'-(Propane-1,3-diyl)bis(2-aminobenzamide). Acta Crystallographica Section E, 69 (5): o673.
  • Sun XL, Fan LX, Yang YJ, Guo Z, Tian WQ, Lei S, 2015. Synthesis of one-dimensional Schiff base polymers that contain an oligothiophene building block on the graphite surface. Chemistry, 21 (18): 6898-6905.
  • Suresh T, Shivaraj, Durgad K, Suresh, 2015. Synthesis Characterization and Biological Studies on Drug Metal Complexes. International Journal of Pharmacy & Life Sciences, 6 (8/9): 4719-4726.
  • Tamer Ö, Avcı D, Atalay Y, 2016. Synthesis, X-Ray crystal structure, photophysical characterization and nonlinear optical properties of the unique manganese complex with picolinate and 1,10 phenantroline: toward the designing of new high NLO response crystal. Journal of Physics and Chemistry of Solids, 99: 124-133.
  • Thompson KH, 1999. Vanadium and diabetes. Biofactors, 10 (1): 43-51.
  • Turkyilmaz M, Uluçam G, Aktaş Ş, Okan SE, 2017. Synthesis and Characterization of New N-Heterocyclic Carbene Ligands: 1,3-Bis(Acetamide)Imidazol-3-Ium Bromide And 3-(Acetamide)-1-(3-Aminopropyl)-1h-Imidazol-3-Ium Bromide. Journal of Molecular Structure, 1136 (Supplement C): 263-270.
  • Ulucam G, 2017. Synthesis, Characterization and Biological Activities of 3-(2-Hydroxyethyl)-1-(3-Aminopropyl)-1HImidazole-3-Ium Bromide. Trakya University Journal of Natural Sciences, 18 (1): 49-54.
  • Ulucam G, Turkyilmaz M, 2018. Synthesis, Structural Analysis, and Biological Activities of Some Imidazolium Salts. Bioinorganic chemistry and applications, 2018: 1439810.
  • Uluçam G, Okan SE, Aktaş Ş, Öğretmen GP, 2015. Characterization of dinaphthosulfoxide molecule. Journal of Molecular Structure, 1102: 146-152.
  • Vela A, Gazquez JL, 1990. A relationship between the static dipole polarizability, the global softness, and the fukui function. Journal of the American Chemical Society, 112 (4): 1490-1492.

(1E,1'E)-N,N'-(hekzan-1,6-diil)bis(1-(tiyofen-2-il)metanimin) ve (1E,1'E)-N,N'-(oktan-1,8-diil)bis(1-(tiyofen-2-il)metanimin) Schiff Baz Ligantlarının Deneysel ve Teorik Karakterizasyonu

Yıl 2019, Cilt: 9 Sayı: 3, 1431 - 1442, 01.09.2019
https://doi.org/10.21597/jist.500254

Öz

Aromatik aldehit olan 2-tiyofen-karboksialdehit sırasıyla 1,6-diaminohekzan ve 1,8-diaminooktan’nın kullanılmasıyla (1E,1'E)-N,N'-(hekzan-1,6-diil)bis(1-(tiyofen-2-il)metanimin) ve (1E,1'E)-N,N'-(oktan-1,8-diil)bis(1-(tiyofen-2-il)metanimin) Schiff baz ligantları elde edildi. Ligantlar fourier transform infrared spektroskopisi (FT-IR), 1H- ve 13C- nükleer manyetik rezonans spektroskopisi (1H- ve 13C- NMR), kütle spektroskopisi (LC ESI/MS) yöntemleri ile karakterize edildi. Ligantların antibakteriyal aktiviteleri araştırıldı. Ayrıca ligantların bağ uzunlukları, bağ açıları, dihedral açıları gibi geometrik özellikleri, elektronik özellikleri, en yüksek dolu moleküler orbital (HOMO) ve en düşük boş moleküler orbital (LUMO) enerjileri Gaussian 09w programı kullanılarak hesaplandı. Deneysel ve teorik spektrum verileri karşılaştırıldı.

Kaynakça

  • Al-Otaibi JS, Al-Wabli RI, 2015. Vibrational spectroscopic investigation (FT-IR and FT-Raman) using ab initio (HF) and DFT (B3LYP) calculations of 3-ethoxymethyl-1,4-dihydroquinolin-4-one. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 137: 7-15.
  • Alkorta I, Perez JJ, 1996. Molecular polarization potential maps of the nucleic acid bases. International Journal of Quantum Chemistry, 57 (1): 123-135.
  • Altürk S, Avcı D, Tamer Ö, Atalay Y, 2018. 1H–pyrazole–3–carboxylic acid: Experimental and computational study. Journal of Molecular Structure, 1164: 28-36.
  • Casella L, Ibers JA, 1981. Synthesis, Characterization, and Reactivity of Copper(I) and Copper(II) Complexes of N,N'-Bis(3-(2-Thenylideneimino)Propyl)Piperazine (Tipp) and N,N'-Bis(3-(2-Thenylamino)Propyl)Piperazine (Tapp). Crystal Structure of [Cu(Tapp)][Clo4]2. Inorganic Chemistry, 20 (8): 2438-2448.
  • Dineshkumar S, Muthusamy A, 2016. Synthesis and Spectral Characterization of Cross Linked Rigid Structured Schiff Base Polymers: Effect of Substituent Position Changes on Optical, Electrical, and Thermal Properties. Polymer-Plastics Technology and Engineering, 55 (4): 368-378.
  • Fedorova EV, Buryakina AV, Vorobieva NM, Baranova NI, 2013. The Vanadium Compounds: Chemistry, Synthesis, Insulinomimetic Properties. Biochemistry (Moscow) Supplement Series B: Biomedical Chemistry, 7 (4): 259-270.
  • Gabr MT, El-Gohary NS, El-Bendary ER, El-Kerdawy MM, Ni N, Shaaban MI, 2015. Synthesis, antimicrobial, antiquorum-sensing and cytotoxic activities of new series of benzothiazole derivatives. Chinese Chemical Letters, 26 (12): 1522-1528.
  • Gadre SR, Shrivastava IH, 1991. Shapes and sizes of molecular anions via topographical analysis of electrostatic potential. The Journal of Chemical Physics, 94 (6): 4384-4390.
  • Gudasi KB, Patil MS, Vadavi RS, Shenoy RV, Patil SA, Nethaji M, 2006. X-ray Crystal Structure of the N-(2-hydroxy-1-naphthalidene)phenylglycine Schiff Base. Synthesis and Characterization of its Transition Metal Complexes. Transition Metal Chemistry, 31 (5): 580-585.
  • Hamada Y, 1997. The development of chelate metal complexes as an organic electroluminescent material. IEEE Transactions on Electron Devices, 44 (8): 1208-1217.
  • Hriday MN, Srivastava RK, Narayan V, S. C, Sachan AK, Shukla VK, Prasad O, Sinha L, 2013. Electronic structure, non-linear properties and vibrational analysis of ortho, meta and para -hydroxybenzaldehyde by density functional theory. Research Journal of Recent Sciences, 2: 150-157.
  • Karakaya C, Dede B, Cicek E, 2016. Novel Metal(II) Complexes with Bidentate Schiff Base Ligand: Synthesis, Spectroscopic Properties and Dye Decolorization Functions. Acta Physica Polonica A, 129 (2): 208-212.
  • Kumar S, Nath Dhar D, N. Saxena P, 2009. Applications of metal complexes of Schiff bases-A review. Journal of scientific and industrial research, 68 (3): 181-187.
  • Luque FJ, Orozco M, Bhadane PK, Gadre SR, 1993. SCRF calculation of the effect of water on the topology of the molecular electrostatic potential. The Journal of Physical Chemistry, 97 (37): 9380-9384.
  • Mihai S, Negoiu M, Bondarev A, 2009. Synthesis, Characterization and Biological Activity of Some Novel Metal Complexes of Schiff Base Derived from p-phenyldiamine and 2-thiophene Carboxaldehyde. Revista de Chimie -Bucharest, 60: 778-782.
  • Murray JS, Sen K. 1996. Molecular Electrostatic Potentials, Concepts and Applications, Elsevier Science, No: 1, pp. 665, Amsterdam-Netherlands
  • Nagy PI, 2013. The syn–anti equilibrium for the COOH group reinvestigated. Theoretical conformation analysis for acetic acid in the gas phase and in solution. Computational and Theoretical Chemistry, 1022: 59-69.
  • Pessoa JC, Etcheverry S, Gambino D, 2015. Vanadium Compounds in Medicine. Coordination Chemistry Reviews, 301-302 (Supplement C): 24-48.
  • Rehder D, 2003. Biological and Medicinal Aspects of Vanadium. Inorganic Chemistry Communications, 6 (5): 604-617.
  • Sreedasyam JS, Sunkari J, Kundha S, Gundapaneni RR, 2013. N,N'-(Propane-1,3-diyl)bis(2-aminobenzamide). Acta Crystallographica Section E, 69 (5): o673.
  • Sun XL, Fan LX, Yang YJ, Guo Z, Tian WQ, Lei S, 2015. Synthesis of one-dimensional Schiff base polymers that contain an oligothiophene building block on the graphite surface. Chemistry, 21 (18): 6898-6905.
  • Suresh T, Shivaraj, Durgad K, Suresh, 2015. Synthesis Characterization and Biological Studies on Drug Metal Complexes. International Journal of Pharmacy & Life Sciences, 6 (8/9): 4719-4726.
  • Tamer Ö, Avcı D, Atalay Y, 2016. Synthesis, X-Ray crystal structure, photophysical characterization and nonlinear optical properties of the unique manganese complex with picolinate and 1,10 phenantroline: toward the designing of new high NLO response crystal. Journal of Physics and Chemistry of Solids, 99: 124-133.
  • Thompson KH, 1999. Vanadium and diabetes. Biofactors, 10 (1): 43-51.
  • Turkyilmaz M, Uluçam G, Aktaş Ş, Okan SE, 2017. Synthesis and Characterization of New N-Heterocyclic Carbene Ligands: 1,3-Bis(Acetamide)Imidazol-3-Ium Bromide And 3-(Acetamide)-1-(3-Aminopropyl)-1h-Imidazol-3-Ium Bromide. Journal of Molecular Structure, 1136 (Supplement C): 263-270.
  • Ulucam G, 2017. Synthesis, Characterization and Biological Activities of 3-(2-Hydroxyethyl)-1-(3-Aminopropyl)-1HImidazole-3-Ium Bromide. Trakya University Journal of Natural Sciences, 18 (1): 49-54.
  • Ulucam G, Turkyilmaz M, 2018. Synthesis, Structural Analysis, and Biological Activities of Some Imidazolium Salts. Bioinorganic chemistry and applications, 2018: 1439810.
  • Uluçam G, Okan SE, Aktaş Ş, Öğretmen GP, 2015. Characterization of dinaphthosulfoxide molecule. Journal of Molecular Structure, 1102: 146-152.
  • Vela A, Gazquez JL, 1990. A relationship between the static dipole polarizability, the global softness, and the fukui function. Journal of the American Chemical Society, 112 (4): 1490-1492.
Toplam 29 adet kaynakça vardır.

Ayrıntılar

Birincil Dil Türkçe
Konular Kimya Mühendisliği
Bölüm Kimya / Chemistry
Yazarlar

Gühergül Uluçam 0000-0001-6481-8483

Büşra Yentürk Bu kişi benim 0000-0003-0009-9752

Yayımlanma Tarihi 1 Eylül 2019
Gönderilme Tarihi 20 Aralık 2018
Kabul Tarihi 7 Mart 2019
Yayımlandığı Sayı Yıl 2019 Cilt: 9 Sayı: 3

Kaynak Göster

APA Uluçam, G., & Yentürk, B. (2019). (1E,1’E)-N,N’-(hekzan-1,6-diil)bis(1-(tiyofen-2-il)metanimin) ve (1E,1’E)-N,N’-(oktan-1,8-diil)bis(1-(tiyofen-2-il)metanimin) Schiff Baz Ligantlarının Deneysel ve Teorik Karakterizasyonu. Journal of the Institute of Science and Technology, 9(3), 1431-1442. https://doi.org/10.21597/jist.500254
AMA Uluçam G, Yentürk B. (1E,1’E)-N,N’-(hekzan-1,6-diil)bis(1-(tiyofen-2-il)metanimin) ve (1E,1’E)-N,N’-(oktan-1,8-diil)bis(1-(tiyofen-2-il)metanimin) Schiff Baz Ligantlarının Deneysel ve Teorik Karakterizasyonu. Iğdır Üniv. Fen Bil Enst. Der. Eylül 2019;9(3):1431-1442. doi:10.21597/jist.500254
Chicago Uluçam, Gühergül, ve Büşra Yentürk. “(1E,1’E)-N,N’-(hekzan-1,6-diil)bis(1-(tiyofen-2-il)metanimin) Ve (1E,1’E)-N,N’-(oktan-1,8-diil)bis(1-(tiyofen-2-il)metanimin) Schiff Baz Ligantlarının Deneysel Ve Teorik Karakterizasyonu”. Journal of the Institute of Science and Technology 9, sy. 3 (Eylül 2019): 1431-42. https://doi.org/10.21597/jist.500254.
EndNote Uluçam G, Yentürk B (01 Eylül 2019) (1E,1’E)-N,N’-(hekzan-1,6-diil)bis(1-(tiyofen-2-il)metanimin) ve (1E,1’E)-N,N’-(oktan-1,8-diil)bis(1-(tiyofen-2-il)metanimin) Schiff Baz Ligantlarının Deneysel ve Teorik Karakterizasyonu. Journal of the Institute of Science and Technology 9 3 1431–1442.
IEEE G. Uluçam ve B. Yentürk, “(1E,1’E)-N,N’-(hekzan-1,6-diil)bis(1-(tiyofen-2-il)metanimin) ve (1E,1’E)-N,N’-(oktan-1,8-diil)bis(1-(tiyofen-2-il)metanimin) Schiff Baz Ligantlarının Deneysel ve Teorik Karakterizasyonu”, Iğdır Üniv. Fen Bil Enst. Der., c. 9, sy. 3, ss. 1431–1442, 2019, doi: 10.21597/jist.500254.
ISNAD Uluçam, Gühergül - Yentürk, Büşra. “(1E,1’E)-N,N’-(hekzan-1,6-diil)bis(1-(tiyofen-2-il)metanimin) Ve (1E,1’E)-N,N’-(oktan-1,8-diil)bis(1-(tiyofen-2-il)metanimin) Schiff Baz Ligantlarının Deneysel Ve Teorik Karakterizasyonu”. Journal of the Institute of Science and Technology 9/3 (Eylül 2019), 1431-1442. https://doi.org/10.21597/jist.500254.
JAMA Uluçam G, Yentürk B. (1E,1’E)-N,N’-(hekzan-1,6-diil)bis(1-(tiyofen-2-il)metanimin) ve (1E,1’E)-N,N’-(oktan-1,8-diil)bis(1-(tiyofen-2-il)metanimin) Schiff Baz Ligantlarının Deneysel ve Teorik Karakterizasyonu. Iğdır Üniv. Fen Bil Enst. Der. 2019;9:1431–1442.
MLA Uluçam, Gühergül ve Büşra Yentürk. “(1E,1’E)-N,N’-(hekzan-1,6-diil)bis(1-(tiyofen-2-il)metanimin) Ve (1E,1’E)-N,N’-(oktan-1,8-diil)bis(1-(tiyofen-2-il)metanimin) Schiff Baz Ligantlarının Deneysel Ve Teorik Karakterizasyonu”. Journal of the Institute of Science and Technology, c. 9, sy. 3, 2019, ss. 1431-42, doi:10.21597/jist.500254.
Vancouver Uluçam G, Yentürk B. (1E,1’E)-N,N’-(hekzan-1,6-diil)bis(1-(tiyofen-2-il)metanimin) ve (1E,1’E)-N,N’-(oktan-1,8-diil)bis(1-(tiyofen-2-il)metanimin) Schiff Baz Ligantlarının Deneysel ve Teorik Karakterizasyonu. Iğdır Üniv. Fen Bil Enst. Der. 2019;9(3):1431-42.