Araştırma Makalesi
BibTex RIS Kaynak Göster

NMR and DSC studies on the reactions of pentanedioxy spiro-ansa cyclochlorotriphosphazene and pentanedioxy triple-bridged cylochlorotriphosphazene with monofunctional nucleophiles

Yıl 2019, Cilt: 23 Sayı: 6, 1177 - 1189, 01.12.2019

Rafig Gurbanov , Murat Tuna , Sedat Türe

https://doi.org/10.16984/saufenbilder.540276

Öz

In this study, the reactions of 2-(2-hydroxyethyl) thiophene (2) and benzyl alcohol (3) with

pentanedioxycyclochlorotriphosphazene (1) and pentanedioxy triple-bridged cylochlorotriphosphazene (6)

were studied. The novel cyclotriphosphazene compounds: two di-substituted spiro-ansa, N 3 P 3 [O(CH 2 ) 5 O]-

(C 6 H 7 OS)] 2 (4) and N 3 P 3 [O(CH 2 ) 5 O-(C 6 H 5 CH 2 O)] 2 (5); and two fully substituted triple-bridged,

N 3 P 3 [O(CH 2 ) 5 O] 3 -(C 6 H 7 OS) 6 N 3 P 3 (7) and N 3 P 3 [O(CH 2 ) 5 O] 3 -(C 6 H 5 CH 2 O) 6 N 3 P 3 (8) derivatives were

formed in THF solvent by using NaH base at ambient conditions. Because of their variety of applications,

there is a great deal of interest in the preparation of aromatic macrocyclic derivatives of cyclophosphazenes.

The main purpose of these studies is to develop bioactive cyclophosphazene derivatives in the search for

new effective drug candidates for the treatment of various diseases, in particular, anticancer and

antimicrobials. The synthesized compounds (4, 5, 7, 8) were defined using analytical techniques namely

Element analysis, TLC/MS system, and NMR spectroscopy. Thermal stabilities, crystal purity, and

recrystallization properties and corresponding enthalpies of synthesized derivatives were analyzed in the

course of heating and cooling cycles of DSC.

Anahtar Kelimeler

Cyclophosphazene spiro-ansa compounds triple-bridged compounds monofunctional nucleophilic reagents Nuclear magnetic resonance spectroscopy

Kaynakça

  • M. El Gouri, A. El Bachiri, S. E. Hegazi, M. Rafik, and A. El Harfi, “Thermal degradation of a reactive flame retardant based on cyclotriphosphazene and its blend with DGEBA epoxy resin,” Polym Degrad Stab., vol. 94, no. 11, pp. 2101–2106, 2009.
  • R. E. Singler, “Historical overview of the army contributions to phosphazene chemistry,” J Inorg Organomet Polym Mater., vol. 16, no. 4. pp. 307–309, 2006.
  • M. Işklan et al., “Phosphorus-nitrogen compounds. 21. Syntheses, structural investigations, biological activities, and DNA interactions of new N/O spirocyclic phosphazene derivatives. the NMR behaviors of chiral phosphazenes with stereogenic centers upon the addition of chi,” Inorg Chem., vol. 49, no. 15, pp. 7057–7071, 2010.
  • N. Asmafiliz et al., “Phosphorus-nitrogen compounds. Part 23: Syntheses, structural investigations, biological activities, and DNA interactions of new N/O spirocyclotriphosphazenes,” Spectrochim Acta A Mol Biomol Spectrosc., vol. 86, pp. 214–223, 2012.
  • H. Akbaş, A. Karadağ, A. Aydın, A. Destegül, and Z. Kılıç, “Synthesis, structural and thermal properties of the hexapyrrolidinocyclotriphosphazenes-based protic molten salts: Antiproliferative effects against HT29, HeLa, and C6 cancer cell lines,” J Mol Liq., vol. 230, pp. 482–495, 2017.
  • E. Cil, M. A. Tanyildizi, F. Ozen, M. Boybay, M. Arslan, and A. O. Gorgulu, “Synthesis, characterization, and biological-pharmacological evaluation of new phosphazenes bearing dioxybiphenyl and Schiff base groups,” Arch Pharm., vol. 345, no. 6, pp. 476–485, 2012.
  • D. Erdener Çıralı, Z. Uyar, İ. Koyuncu, and N. Hacıoğlu, “Synthesis , characterization and catalytic , cytotoxic and antimicrobial activities of two novel cyclotriphosphazene-based multisite ligands and their Ru ( II ) complexes,” Appl Organomet Chem., vol. 29, no. 8, pp. 536–542, 2015.
  • A. Uslu, E. Özcan, S. Dural, and F. Yuksel, “Synthesis and characterization of cyclotriphosphazene derivatives bearing azole groups,” Polyhedron, vol. 117, pp. 394–403, 2016.
  • M. Siwy et al., “Synthesis and in vitro antileukemic activity of some new 1,3-(oxytetraethylenoxy)cyclotriphosphazene derivatives,” J Med Chem., vol. 49, no. 2, pp. 806–810, 2006.
  • S. S. Machakanur, B. R. Patil, G. N. Naik, R. P. Bakale, S. W. Annie Bligh, and K. B. Gudasi, “Synthesis, characterization and antiproliferative activity of hexa arm star shaped thiosemicarbazones derived from cyclotriphosphazene core,” Inorganica Chim. Acta, vol. 421, pp. 459–464, 2014.
  • T. Yildirim et al., “Synthesis, cytotoxicity and apoptosis of cyclotriphosphazene compounds as anti-cancer agents,” Eur J Med Chem., vol. 52, pp. 213–220, 2012.
  • H. Akbaş et al., “Phosphorus-nitrogen compounds part 27. Syntheses, structural characterizations, antimicrobial and cytotoxic activities, and DNA interactions of new phosphazenes bearing secondary amino and pendant (4-fluorobenzyl)spiro groups,” Eur J Med Chem., vol. 70, pp. 294–307, 2013.
  • A. O. Görgülü, K. Koran, F. Özen, S. Tekin, and S. Sandal, “Synthesis, structural characterization and anti-carcinogenic activity of new cyclotriphosphazenes containing dioxybiphenyl and chalcone groups,” J Mol Struct., vol. 1087, pp. 1–10, 2015.
  • S. V. Levchik, G. Camino, M. P. Luda, L. Costa, A. Lindsay, and D. Stevenson, “Thermal decomposition of cyclotriphosphazenes. I. Alkyl-aminoaryl ethers,” J Appl Polym Sci., vol. 67, no. 3, pp. 461–472, 1998.
  • R. Liu and X. Wang, “Synthesis, characterization, thermal properties and flame retardancy of a novel nonflammable phosphazene-based epoxy resin,” Polym Degrad Stab., vol. 94, no. 4, pp. 617–624, 2009.
  • R. Horvath, C. A. Otter, K. C. Gordon, A. M. Brodie, and E. W. Ainscough, “Excited states of Ru(II) and Re(I) bipyridyl complexes attached to cyclotriphosphazenes: A synthetic, spectroscopic, and computational study,” Inorg Chem., vol. 49, no. 9, pp. 4073–4083, 2010.
  • S. Devaraju, M. Selvi, and M. Alagar, “Synthesis and characterization of thermally stable and flame retardant hexakis ( 4- polyimide matrices,” Int J Polym Anal Charact., vol. 23, no. 1, pp. 29–37, 2018.
  • S. Zhang et al., “Preparation of Poly(bis(phenoxy)phosphazene) and 31P NMR Analysis of Its Structural Defects under Various Synthesis Conditions,” J Phys Chem B., vol. 120, no. 43, pp. 11307–11316, 2016.
  • H. A. Alidağı, F. Hacıvelioğlu, S. O. Tümay, B. Çoşut, and S. Yeşilot, “Synthesis and spectral properties of fluorene substituted cyclic and polymeric phosphazenes,” Inorg Chim Acta., vol. 457, pp. 95–102, 2017.
  • K. Krishnadevi, V. Selvaraj, and D. Prasanna, “Thermal, mechanical and antibacterial properties of cyclophosphazene incorporated benzoxazine blended bismaleimide composites,” RSC Adv., vol. 5, pp. 913–921, 2015.
  • B. P. Woods and T. R. Hoye, “Differential scanning calorimetry (DSC) as a tool for probing the reactivity of polyynes relevant to hexadehydro-diels-alder (HDDA) cascades,” Org Lett., vol. 16, no. 24, pp. 6370–6373, 2014.
  • Z. S. Eren, S. Tunçer, G. Gezer, L. T. Yildirim, S. Banerjee, and A. Yilmaz, “Improved solubility of celecoxib by inclusion in SBA-15 mesoporous silica: Drug loading in different solvents and release,” Microporous Mesoporous Mater., vol. 235, pp. 211–223, 2016.
  • S. Beşli, S. J. Coles, D. B. Davies, M. B. Hursthouse, A. Kiliç, and R. a Shaw, “A spiro to ansa rearrangement in cyclotriphosphazene derivatives.,” Dalt. Trans., vol. 14, no. 26, pp. 2792–2801, 2007.
  • D. Palabıyık, C. Mutlu Balcı, and S. Beşli, “The role of the substituted group on competitive formation of ansa and spiro isomers,” Inorg Chim Acta., vol. 487, pp. 15–23, 2019.
  • S. Beşli et al., “Competitive formation of cis and trans derivatives in the nucleophilic substitution reactions of cyclophosphazenes having a mono-spiro P-NHR group,” Dalt. Trans., vol. 40, no. 18, pp. 4959–4969, 2011.
  • G. Guerch, L. Jean-François, R. Lahana, R. Roques, and F. Sournies, “An answer to the spiro versus ansa dilemma in cyclophosphazenes. Part III. N3P3Cl5[HN(CH2)4NH]Cl5P3N3. A serendipitous two-ring bridged-assembly phosphazene,” J Mol Struct., vol. 99, no. 3–4, pp. 275–282, 1983.
  • P. Castera et al., “An answer to the SPIRO versus ANSA dilemma in cyclophosphazenes. Part VII. Neither SPIRO nor ANSA: the BINOdicyclotriphosphazenes, N3P3Cl5 [HN(CH2)nNH] Cl5P3N3,” Inorganica Chim. Acta, vol. 108, no. 1, pp. 29–33, 1985.
  • H. A. Al-Madfa, R. A. Shaw, and S. Ture, “Phosphorus-Nitrogen compounds. part 64.1 the reactions of hexachlorocyclotriphosphazatriene with 2, 2-dimethylpropane-l, 3-diol. nuclear magnetic resonance studies of the products,” Phosphorus Sulfur Silicon Relat Elem., vol. 53, no. 1–4, pp. 333–338, 1990.
  • A. S. Freund, M. Calichman, and C. W. Allen, “The reactions of hexafluorocyclotriphosphazene with sodium phenoxide,” Z Anorg Allg Chem., vol. 630, no. 12, pp. 2059–2062, 2004.
  • S. Beşli, S. Doğan, C. Mutlu Balcı, and F. Yuksel, “The reaction of N,N-spiro bridged octachlorobis(cyclotriphosphazene) with 1,3-propanediol: Comparison with 1,2-ethanediol,” Polyhedron, vol. 122, pp. 61–70, 2017.
  • S. Ture and R. Gurbanov, “Synthesis and structural characterization of geminal and non-geminal 1,1,3,3-tetramethylguanidine substituted derivatives of cyclotriphosphazene: Thermal and spectroscopic investigations of the products,” Phosphorus Sulfur Silicon Relat Elem., vol. 193, no. 10, pp. 620–629, 2018.
  • S. Ture, R. Gurbanov, and M. Tuna, “Reactions of cyclochlorotriphosphazatriene with 2-mercaptoethanol. Calorimetric and spectroscopic investigations of the derived products,” Phosphorus Sulfur Silicon Relat Elem., vol. 193, no. 9, pp. 600–610, 2018.
  • J. Barberá et al., “Columnar mesomorphic organizations in cyclotriphosphazenes,” J Am Chem Soc., vol. 127, no. 25, pp. 8994–9002, 2005.
  • S. Ture and Ö. Kücük, “The reactions of non-gem- hexanedioxytetrachlorocyclotriphosphazene with 2- ( 2-hydroxyethyl ) thiophene , benzyl alcohol,” Phosphorus Sulfur Silicon Relat Elem., vol. 0, no. 0, pp. 1–8, 2019.
  • E. E. Ilter et al., “Phosphorus-nitrogen compounds: Part 19. Syntheses, structural and electrochemical investigations, biological activities, and DNA interactions of new spirocyclic monoferrocenylcyclotriphosphazenes,” Polyhedron, vol. 29, no. 15, pp. 2933–2944, 2010.
  • S. Ture, “Phosphorus-nitrogen compounds: Reinvestigation of the reactions of hexachlorocyclotriphosphazene with 1,4-butane- and 1,6-hexane-diols—NMR studies of the products,” Phosphorus Sulfur Silicon Relat Elem., vol. 191, no. 8, pp. 1174–1182, 2016.
  • S. Ture, “The Reactions of Octachlorocyclotetraphosphazene with Difunctional Bis(2-Hydroxyethyl) Ether. Nuclear Magnetic Studies of the Products,” Phosphorus Sulfur Silicon Relat Elem., vol. 189, no. 11, pp. 1746–1767, 2014.
  • R. A. Shaw and S. Ture, “Phosphorus-nitrogen compounds. part 711. the reactions of hexachlorocyclotriphosphazatriene with bis (2-hydroxyethyl) ether. nuclear magnetic resonance spectroscopic studies of the products,” Phosphorus Sulfur Silicon Relat Elem., vol. 57, no. 1–2, pp. 103–109, 1991.
  • S. Beşli, H. Ibişoǧlu, A. Kiliç, I. Ün, and F. Yuksel, “Spiro, ansa-derivatives of cyclotetraphosphazenes with a tetrafluorobutane-1,4-diol,” Polyhedron, vol. 29, no. 17, pp. 3220–3228, 2010.
  • S. Beşli et al., “A cis-directing effect towards diols by an exocyclic P-NHR moiety in cyclotriphosphazenes,” Inorg Chem Commun., vol. 12, no. 8, pp. 773–777, 2009.
  • E. T. Eçik, S. Beşli, G. Y. Çiftçi, D. B. Davies, A. Kiliç, and F. Yuksel, “Stereo-selectivity in a cyclotriphosphazene derivative bearing an exocyclic P-O moiety,” Dalt. Trans., vol. 41, no. 22, pp. 6715–6725, 2012.
  • S. Beşli, S. J. Coles, L. S. Coles, D. B. Davies, and A. Kiliç, “Investigation of a spiro to ansa rearrangement with di-functional alcohols in cyclotriphosphazene derivatives,” Polyhedron, vol. 43, no. 1, pp. 176–184, 2012.
  • S. Ture, “Phosphorus-Nitrogen Compounds: The Reactions of Hexachlorocyclotriphosphazatriene with Pentane-1,5-Diol. Nuclear Magnetic Resonance Studies of The Products,” Phosphorus Sulfur Silicon Relat Elem., vol. 188, no. 9, pp. 1156–1171, 2013.

Yıl 2019, Cilt: 23 Sayı: 6, 1177 - 1189, 01.12.2019

Rafig Gurbanov , Murat Tuna , Sedat Türe

https://doi.org/10.16984/saufenbilder.540276

Öz

Kaynakça

  • M. El Gouri, A. El Bachiri, S. E. Hegazi, M. Rafik, and A. El Harfi, “Thermal degradation of a reactive flame retardant based on cyclotriphosphazene and its blend with DGEBA epoxy resin,” Polym Degrad Stab., vol. 94, no. 11, pp. 2101–2106, 2009.
  • R. E. Singler, “Historical overview of the army contributions to phosphazene chemistry,” J Inorg Organomet Polym Mater., vol. 16, no. 4. pp. 307–309, 2006.
  • M. Işklan et al., “Phosphorus-nitrogen compounds. 21. Syntheses, structural investigations, biological activities, and DNA interactions of new N/O spirocyclic phosphazene derivatives. the NMR behaviors of chiral phosphazenes with stereogenic centers upon the addition of chi,” Inorg Chem., vol. 49, no. 15, pp. 7057–7071, 2010.
  • N. Asmafiliz et al., “Phosphorus-nitrogen compounds. Part 23: Syntheses, structural investigations, biological activities, and DNA interactions of new N/O spirocyclotriphosphazenes,” Spectrochim Acta A Mol Biomol Spectrosc., vol. 86, pp. 214–223, 2012.
  • H. Akbaş, A. Karadağ, A. Aydın, A. Destegül, and Z. Kılıç, “Synthesis, structural and thermal properties of the hexapyrrolidinocyclotriphosphazenes-based protic molten salts: Antiproliferative effects against HT29, HeLa, and C6 cancer cell lines,” J Mol Liq., vol. 230, pp. 482–495, 2017.
  • E. Cil, M. A. Tanyildizi, F. Ozen, M. Boybay, M. Arslan, and A. O. Gorgulu, “Synthesis, characterization, and biological-pharmacological evaluation of new phosphazenes bearing dioxybiphenyl and Schiff base groups,” Arch Pharm., vol. 345, no. 6, pp. 476–485, 2012.
  • D. Erdener Çıralı, Z. Uyar, İ. Koyuncu, and N. Hacıoğlu, “Synthesis , characterization and catalytic , cytotoxic and antimicrobial activities of two novel cyclotriphosphazene-based multisite ligands and their Ru ( II ) complexes,” Appl Organomet Chem., vol. 29, no. 8, pp. 536–542, 2015.
  • A. Uslu, E. Özcan, S. Dural, and F. Yuksel, “Synthesis and characterization of cyclotriphosphazene derivatives bearing azole groups,” Polyhedron, vol. 117, pp. 394–403, 2016.
  • M. Siwy et al., “Synthesis and in vitro antileukemic activity of some new 1,3-(oxytetraethylenoxy)cyclotriphosphazene derivatives,” J Med Chem., vol. 49, no. 2, pp. 806–810, 2006.
  • S. S. Machakanur, B. R. Patil, G. N. Naik, R. P. Bakale, S. W. Annie Bligh, and K. B. Gudasi, “Synthesis, characterization and antiproliferative activity of hexa arm star shaped thiosemicarbazones derived from cyclotriphosphazene core,” Inorganica Chim. Acta, vol. 421, pp. 459–464, 2014.
  • T. Yildirim et al., “Synthesis, cytotoxicity and apoptosis of cyclotriphosphazene compounds as anti-cancer agents,” Eur J Med Chem., vol. 52, pp. 213–220, 2012.
  • H. Akbaş et al., “Phosphorus-nitrogen compounds part 27. Syntheses, structural characterizations, antimicrobial and cytotoxic activities, and DNA interactions of new phosphazenes bearing secondary amino and pendant (4-fluorobenzyl)spiro groups,” Eur J Med Chem., vol. 70, pp. 294–307, 2013.
  • A. O. Görgülü, K. Koran, F. Özen, S. Tekin, and S. Sandal, “Synthesis, structural characterization and anti-carcinogenic activity of new cyclotriphosphazenes containing dioxybiphenyl and chalcone groups,” J Mol Struct., vol. 1087, pp. 1–10, 2015.
  • S. V. Levchik, G. Camino, M. P. Luda, L. Costa, A. Lindsay, and D. Stevenson, “Thermal decomposition of cyclotriphosphazenes. I. Alkyl-aminoaryl ethers,” J Appl Polym Sci., vol. 67, no. 3, pp. 461–472, 1998.
  • R. Liu and X. Wang, “Synthesis, characterization, thermal properties and flame retardancy of a novel nonflammable phosphazene-based epoxy resin,” Polym Degrad Stab., vol. 94, no. 4, pp. 617–624, 2009.
  • R. Horvath, C. A. Otter, K. C. Gordon, A. M. Brodie, and E. W. Ainscough, “Excited states of Ru(II) and Re(I) bipyridyl complexes attached to cyclotriphosphazenes: A synthetic, spectroscopic, and computational study,” Inorg Chem., vol. 49, no. 9, pp. 4073–4083, 2010.
  • S. Devaraju, M. Selvi, and M. Alagar, “Synthesis and characterization of thermally stable and flame retardant hexakis ( 4- polyimide matrices,” Int J Polym Anal Charact., vol. 23, no. 1, pp. 29–37, 2018.
  • S. Zhang et al., “Preparation of Poly(bis(phenoxy)phosphazene) and 31P NMR Analysis of Its Structural Defects under Various Synthesis Conditions,” J Phys Chem B., vol. 120, no. 43, pp. 11307–11316, 2016.
  • H. A. Alidağı, F. Hacıvelioğlu, S. O. Tümay, B. Çoşut, and S. Yeşilot, “Synthesis and spectral properties of fluorene substituted cyclic and polymeric phosphazenes,” Inorg Chim Acta., vol. 457, pp. 95–102, 2017.
  • K. Krishnadevi, V. Selvaraj, and D. Prasanna, “Thermal, mechanical and antibacterial properties of cyclophosphazene incorporated benzoxazine blended bismaleimide composites,” RSC Adv., vol. 5, pp. 913–921, 2015.
  • B. P. Woods and T. R. Hoye, “Differential scanning calorimetry (DSC) as a tool for probing the reactivity of polyynes relevant to hexadehydro-diels-alder (HDDA) cascades,” Org Lett., vol. 16, no. 24, pp. 6370–6373, 2014.
  • Z. S. Eren, S. Tunçer, G. Gezer, L. T. Yildirim, S. Banerjee, and A. Yilmaz, “Improved solubility of celecoxib by inclusion in SBA-15 mesoporous silica: Drug loading in different solvents and release,” Microporous Mesoporous Mater., vol. 235, pp. 211–223, 2016.
  • S. Beşli, S. J. Coles, D. B. Davies, M. B. Hursthouse, A. Kiliç, and R. a Shaw, “A spiro to ansa rearrangement in cyclotriphosphazene derivatives.,” Dalt. Trans., vol. 14, no. 26, pp. 2792–2801, 2007.
  • D. Palabıyık, C. Mutlu Balcı, and S. Beşli, “The role of the substituted group on competitive formation of ansa and spiro isomers,” Inorg Chim Acta., vol. 487, pp. 15–23, 2019.
  • S. Beşli et al., “Competitive formation of cis and trans derivatives in the nucleophilic substitution reactions of cyclophosphazenes having a mono-spiro P-NHR group,” Dalt. Trans., vol. 40, no. 18, pp. 4959–4969, 2011.
  • G. Guerch, L. Jean-François, R. Lahana, R. Roques, and F. Sournies, “An answer to the spiro versus ansa dilemma in cyclophosphazenes. Part III. N3P3Cl5[HN(CH2)4NH]Cl5P3N3. A serendipitous two-ring bridged-assembly phosphazene,” J Mol Struct., vol. 99, no. 3–4, pp. 275–282, 1983.
  • P. Castera et al., “An answer to the SPIRO versus ANSA dilemma in cyclophosphazenes. Part VII. Neither SPIRO nor ANSA: the BINOdicyclotriphosphazenes, N3P3Cl5 [HN(CH2)nNH] Cl5P3N3,” Inorganica Chim. Acta, vol. 108, no. 1, pp. 29–33, 1985.
  • H. A. Al-Madfa, R. A. Shaw, and S. Ture, “Phosphorus-Nitrogen compounds. part 64.1 the reactions of hexachlorocyclotriphosphazatriene with 2, 2-dimethylpropane-l, 3-diol. nuclear magnetic resonance studies of the products,” Phosphorus Sulfur Silicon Relat Elem., vol. 53, no. 1–4, pp. 333–338, 1990.
  • A. S. Freund, M. Calichman, and C. W. Allen, “The reactions of hexafluorocyclotriphosphazene with sodium phenoxide,” Z Anorg Allg Chem., vol. 630, no. 12, pp. 2059–2062, 2004.
  • S. Beşli, S. Doğan, C. Mutlu Balcı, and F. Yuksel, “The reaction of N,N-spiro bridged octachlorobis(cyclotriphosphazene) with 1,3-propanediol: Comparison with 1,2-ethanediol,” Polyhedron, vol. 122, pp. 61–70, 2017.
  • S. Ture and R. Gurbanov, “Synthesis and structural characterization of geminal and non-geminal 1,1,3,3-tetramethylguanidine substituted derivatives of cyclotriphosphazene: Thermal and spectroscopic investigations of the products,” Phosphorus Sulfur Silicon Relat Elem., vol. 193, no. 10, pp. 620–629, 2018.
  • S. Ture, R. Gurbanov, and M. Tuna, “Reactions of cyclochlorotriphosphazatriene with 2-mercaptoethanol. Calorimetric and spectroscopic investigations of the derived products,” Phosphorus Sulfur Silicon Relat Elem., vol. 193, no. 9, pp. 600–610, 2018.
  • J. Barberá et al., “Columnar mesomorphic organizations in cyclotriphosphazenes,” J Am Chem Soc., vol. 127, no. 25, pp. 8994–9002, 2005.
  • S. Ture and Ö. Kücük, “The reactions of non-gem- hexanedioxytetrachlorocyclotriphosphazene with 2- ( 2-hydroxyethyl ) thiophene , benzyl alcohol,” Phosphorus Sulfur Silicon Relat Elem., vol. 0, no. 0, pp. 1–8, 2019.
  • E. E. Ilter et al., “Phosphorus-nitrogen compounds: Part 19. Syntheses, structural and electrochemical investigations, biological activities, and DNA interactions of new spirocyclic monoferrocenylcyclotriphosphazenes,” Polyhedron, vol. 29, no. 15, pp. 2933–2944, 2010.
  • S. Ture, “Phosphorus-nitrogen compounds: Reinvestigation of the reactions of hexachlorocyclotriphosphazene with 1,4-butane- and 1,6-hexane-diols—NMR studies of the products,” Phosphorus Sulfur Silicon Relat Elem., vol. 191, no. 8, pp. 1174–1182, 2016.
  • S. Ture, “The Reactions of Octachlorocyclotetraphosphazene with Difunctional Bis(2-Hydroxyethyl) Ether. Nuclear Magnetic Studies of the Products,” Phosphorus Sulfur Silicon Relat Elem., vol. 189, no. 11, pp. 1746–1767, 2014.
  • R. A. Shaw and S. Ture, “Phosphorus-nitrogen compounds. part 711. the reactions of hexachlorocyclotriphosphazatriene with bis (2-hydroxyethyl) ether. nuclear magnetic resonance spectroscopic studies of the products,” Phosphorus Sulfur Silicon Relat Elem., vol. 57, no. 1–2, pp. 103–109, 1991.
  • S. Beşli, H. Ibişoǧlu, A. Kiliç, I. Ün, and F. Yuksel, “Spiro, ansa-derivatives of cyclotetraphosphazenes with a tetrafluorobutane-1,4-diol,” Polyhedron, vol. 29, no. 17, pp. 3220–3228, 2010.
  • S. Beşli et al., “A cis-directing effect towards diols by an exocyclic P-NHR moiety in cyclotriphosphazenes,” Inorg Chem Commun., vol. 12, no. 8, pp. 773–777, 2009.
  • E. T. Eçik, S. Beşli, G. Y. Çiftçi, D. B. Davies, A. Kiliç, and F. Yuksel, “Stereo-selectivity in a cyclotriphosphazene derivative bearing an exocyclic P-O moiety,” Dalt. Trans., vol. 41, no. 22, pp. 6715–6725, 2012.
  • S. Beşli, S. J. Coles, L. S. Coles, D. B. Davies, and A. Kiliç, “Investigation of a spiro to ansa rearrangement with di-functional alcohols in cyclotriphosphazene derivatives,” Polyhedron, vol. 43, no. 1, pp. 176–184, 2012.
  • S. Ture, “Phosphorus-Nitrogen Compounds: The Reactions of Hexachlorocyclotriphosphazatriene with Pentane-1,5-Diol. Nuclear Magnetic Resonance Studies of The Products,” Phosphorus Sulfur Silicon Relat Elem., vol. 188, no. 9, pp. 1156–1171, 2013.
Toplam 43 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Bölüm Araştırma Makalesi
Yazarlar

Rafig Gurbanov 0000-0002-5293-6447

Murat Tuna 0000-0002-8554-903X

Sedat Türe 0000-0001-8637-5580

Yayımlanma Tarihi 1 Aralık 2019
Gönderilme Tarihi 15 Mart 2019
Kabul Tarihi 16 Ağustos 2019
Yayımlandığı Sayı Yıl 2019 Cilt: 23 Sayı: 6

Kaynak Göster

APA Gurbanov, R., Tuna, M., & Türe, S. (2019). NMR and DSC studies on the reactions of pentanedioxy spiro-ansa cyclochlorotriphosphazene and pentanedioxy triple-bridged cylochlorotriphosphazene with monofunctional nucleophiles. Sakarya University Journal of Science, 23(6), 1177-1189. https://doi.org/10.16984/saufenbilder.540276
AMA Gurbanov R, Tuna M, Türe S. NMR and DSC studies on the reactions of pentanedioxy spiro-ansa cyclochlorotriphosphazene and pentanedioxy triple-bridged cylochlorotriphosphazene with monofunctional nucleophiles. SAUJS. Aralık 2019;23(6):1177-1189. doi:10.16984/saufenbilder.540276
Chicago Gurbanov, Rafig, Murat Tuna, ve Sedat Türe. “NMR and DSC Studies on the Reactions of Pentanedioxy Spiro-Ansa Cyclochlorotriphosphazene and Pentanedioxy Triple-Bridged Cylochlorotriphosphazene With Monofunctional Nucleophiles”. Sakarya University Journal of Science 23, sy. 6 (Aralık 2019): 1177-89. https://doi.org/10.16984/saufenbilder.540276.
EndNote Gurbanov R, Tuna M, Türe S (01 Aralık 2019) NMR and DSC studies on the reactions of pentanedioxy spiro-ansa cyclochlorotriphosphazene and pentanedioxy triple-bridged cylochlorotriphosphazene with monofunctional nucleophiles. Sakarya University Journal of Science 23 6 1177–1189.
IEEE R. Gurbanov, M. Tuna, ve S. Türe, “NMR and DSC studies on the reactions of pentanedioxy spiro-ansa cyclochlorotriphosphazene and pentanedioxy triple-bridged cylochlorotriphosphazene with monofunctional nucleophiles”, SAUJS, c. 23, sy. 6, ss. 1177–1189, 2019, doi: 10.16984/saufenbilder.540276.
ISNAD Gurbanov, Rafig vd. “NMR and DSC Studies on the Reactions of Pentanedioxy Spiro-Ansa Cyclochlorotriphosphazene and Pentanedioxy Triple-Bridged Cylochlorotriphosphazene With Monofunctional Nucleophiles”. Sakarya University Journal of Science 23/6 (Aralık 2019), 1177-1189. https://doi.org/10.16984/saufenbilder.540276.
JAMA Gurbanov R, Tuna M, Türe S. NMR and DSC studies on the reactions of pentanedioxy spiro-ansa cyclochlorotriphosphazene and pentanedioxy triple-bridged cylochlorotriphosphazene with monofunctional nucleophiles. SAUJS. 2019;23:1177–1189.
MLA Gurbanov, Rafig vd. “NMR and DSC Studies on the Reactions of Pentanedioxy Spiro-Ansa Cyclochlorotriphosphazene and Pentanedioxy Triple-Bridged Cylochlorotriphosphazene With Monofunctional Nucleophiles”. Sakarya University Journal of Science, c. 23, sy. 6, 2019, ss. 1177-89, doi:10.16984/saufenbilder.540276.
Vancouver Gurbanov R, Tuna M, Türe S. NMR and DSC studies on the reactions of pentanedioxy spiro-ansa cyclochlorotriphosphazene and pentanedioxy triple-bridged cylochlorotriphosphazene with monofunctional nucleophiles. SAUJS. 2019;23(6):1177-89.
 Kapak Resmi İndir

30930 This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.