1,3-bis(2-methoxyphenyl)triazene & 1,3-bis(2-methoxyphenyl)triazene as Ligand and their Complex with Hg cations
Thesis advisor:
Mohammad R. Melardi; Ph.D.
Consulting advisor:
Mohammad K. Rofouei; Ph.D.
By:
Mohammad Barkhi
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Islamic Azad University- Karaj Branch Faculty of Science Department of Chemistry Subject: Synthesis, Separation and Spectroscopic and Structural study. презентация
Содержание
- 2. Islamic Azad University- Karaj Branch Faculty of
- 3. Triazenes Triazenes are a class of organic
- 4. Application of Triazenes ◘ In medicine ◘
- 5. ◘ Polymer & Laser industries Triazene polymers
- 6. Properties of triazene ligand with Aryl groups
- 7. Preparation methods There are several methods to
- 8. The coordination properties of 1,3-diphenyltriazene was found
- 9. N1,N3-bidentate ligand [Hg(N3(Ph(OCH3))2)(Cl)] M. R. Melardi; Analytical Sciences 2007
- 10. N1,N3-bidentate bridging ligand [Pd(PhN3C4H8N3Ph)]2 Estela dos Reis Crespan 2005
- 11. N1,N3-tridentate bridging ligand [Tl(RC6H4N3C6H4R)]2 Inorganica Chimica Acta 2006
- 12. N1,N3-tetradentate bridging ligand [Tl(NO2C6H4N3C6H4NO2)]2 Estela dos Reis Crespan 2005
- 13. Preparation methods of Aryltriazene complexes with metals
- 14. Experimental . . .
- 15. 1,3-bis(2-methoxyphenyl)triazene synthesis M.p= 95- 97 °C M.w=
- 16. Mercury complex preparation Hg (s) + Hg2+
- 17. Elemental Analysis Mercury identification in complex
- 18. ►IR spectra Ligand Complex 3352 1623 393 Spectroscopic studies
- 19. ►1H-NMR spectra Ligand Complex
- 20. ►13C-NMR spectra Ligand Complex
- 21. Molecular structure of Mercury complex
- 22. ORTEP view of Mercury complex
- 23. Crystal packing fragment along a crystal axes
- 24. Crystal data for Mercury complex
- 25. (I) (II) [Hg(N3(Ph(OCH3))2)(Cl)] [Hg(RC6H4N3C6H4R)2Py]
- 27. 1,3- bis(2-cyanophenyl)triazene was synthesized first time
- 28. Mercury complex preparation L=1,3- bis(2-cyanophenyl)triazene Decomposes at 238.3 °C M.w= 694.13 g.mol-1 Yield= 44.26 %
- 29. Mercury identification in complex ►
- 30. ► UV-Visible spectra Spectroscopic studies
- 31. ► IR spectra Ligand Complex 2233 3222 1604 2213
- 32. ► 1H-NMR spectra Ligand Complex
- 33. ► 13C-NMR spectra Ligand Complex
- 34. ► X-ray diffraction crystallography For Mercury
- 35. Centrosymmetric H-bonded dimmers of molecules of type A & A'.
- 36. General view of molecule of type A & A'.
- 37. Stacking interaction between molecules of type A & A‘.
- 38. Crystal packing of 1,3-bis(2-cyanophenyl)triazene
- 39. conclusion ► Elemental analysis & spectroscopic studies
- 41. Special thanks to: Dr. Mohammad R. Melardi
Islamic Azad University- Karaj Branch Faculty of Science Department of Chemistry Subject: Synthesis, Separation and Spectroscopic and Structural study on 1,3-bis(2-methoxyphenyl)triazene & 1,3-bis(2-methoxyphenyl)triazene as Ligand and their Complex with
Слайд 2Islamic Azad University- Karaj Branch
Faculty of Science
Department of Chemistry
Subject:
Synthesis, Separation and
Spectroscopic and Structural study on
1,3-bis(2-methoxyphenyl)triazene & 1,3-bis(2-methoxyphenyl)triazene as Ligand and their Complex with Hg cations
1,3-bis(2-methoxyphenyl)triazene & 1,3-bis(2-methoxyphenyl)triazene as Ligand and their Complex with Hg cations
Слайд 3Triazenes
Triazenes are a class of organic compounds characterized by the presence
of diazoamino functional group (N═N─N). The simplest member of the family is known just as Triazene.
These compounds have been used in a variety of application;
in transition metal complexes as ligand (in Triazenide form), in polymer synthesis and anticancer drugs.
J. Am. Chem. Soc. 1988
Inorg. Chem. 2005
Слайд 4Application of Triazenes
◘ In medicine
◘ Poisonous Cations & Anions such as
Mercury, Cadmium,
Cyanide, . . . Separation from environment (J. Org. Chem. 2006:
Analytica Chimica Acta 2005)
Cyanide, . . . Separation from environment (J. Org. Chem. 2006:
Analytica Chimica Acta 2005)
Pharmacological Research (2007)
◘ In food & cosmetics industries as dye (11th report on carcinogens)
Dacarbazine
Temozolomide
Слайд 5◘ Polymer & Laser industries
Triazene polymers revealed superior properties for applications
in the near-IR which could be used as a thruster for micro satellites.
(J. Photochem. Photobio. A 2001)
◘ Complexation with metal cations
Triazenes can act as ligand in metal complexes. There are
many report in this field.
Слайд 6Properties of triazene ligand with Aryl groups as 1,3-substituents (Ar─N═N─NH─Ar) have
been intensely studied during the past years. The simplest Aryltriazene is 1,3- diphenyltriazne (Hdpt).
Слайд 7Preparation methods
There are several methods to preparation Aryltriazenes:
1. By the
action of sodium nitrite on aniline (routine method) (1937).
2. By the action of ammonium nitrate and hydrogen sulfide on
aniline hydrochloride in the presence of iron(1913).
3. By the action of silver nitrite on aniline hydrochloride(1897).
4. Diazotization of aniline, aniline hydrochloride, and
aniline sulfate with sodium nitrite and silver nitrite(1897).
2. By the action of ammonium nitrate and hydrogen sulfide on
aniline hydrochloride in the presence of iron(1913).
3. By the action of silver nitrite on aniline hydrochloride(1897).
4. Diazotization of aniline, aniline hydrochloride, and
aniline sulfate with sodium nitrite and silver nitrite(1897).
Слайд 8The coordination properties of 1,3-diphenyltriazene was found to be:
N1-monodentate ligand
Trans-Pd[3-(2-flurophenil)-1-(4-nitrophenil)triazenido]2(C5H5N)2
Estela dos Reis Crespan 2005
Слайд 13Preparation methods of Aryltriazene complexes with metals
There are several methods to
prepare this complexes;
Such as:
Reaction of metal carboxylate with Aryltriazenes(1941).
Reaction of metal halide with Lithium triazenid complex
(1973).
Reaction of metal salt with Aryltriazene next to triethylamine & heat(2003).
Reaction of metal hydride or metal alkyl with Aryltriazene
(1979).
etc…
Such as:
Reaction of metal carboxylate with Aryltriazenes(1941).
Reaction of metal halide with Lithium triazenid complex
(1973).
Reaction of metal salt with Aryltriazene next to triethylamine & heat(2003).
Reaction of metal hydride or metal alkyl with Aryltriazene
(1979).
etc…
Слайд 151,3-bis(2-methoxyphenyl)triazene synthesis
M.p= 95- 97 °C
M.w= 257.29 g.mol-1
Yield= 46.64 %
Anal. Sci. 2006
Single
crystals in diethylether were obtained.
Слайд 16Mercury complex preparation
Hg (s) + Hg2+ (aq)
[Hg2]2+(aq)
M.p= 122- 127 °C
M.w=
713.15 g.mol-1
Yield= 39.43 %
Yield= 39.43 %
L= 1,3-bis(2-methoxyphenyl)triazene
Inorganica Chimica Acta 2007
Слайд 17Elemental Analysis
Mercury identification in complex
► using diphenylcarbazide
► using Sodium
hydroxide (especially for Hg2+ ion)
Hg2+ + 2OHˉ → HgO↓ + H2O
► using Potassium iodide
Hg2+ (aq) + 2I‾ (aq) → HgI2↓
Hg2+ + 2OHˉ → HgO↓ + H2O
► using Potassium iodide
Hg2+ (aq) + 2I‾ (aq) → HgI2↓
Слайд 271,3- bis(2-cyanophenyl)triazene was synthesized first time
like to 1,3- bis(2-cyanophenyl)triazene.
M.p= 125.6
-129.3 °C
M.w= 247.26 g.mol-1
Yield= 95.25 %
M.w= 247.26 g.mol-1
Yield= 95.25 %
Single crystals in diethylether were obtained.
Слайд 28Mercury complex preparation
L=1,3- bis(2-cyanophenyl)triazene
Decomposes at 238.3 °C
M.w= 694.13 g.mol-1
Yield= 44.26 %
Слайд 29Mercury identification in complex
► using diphenylcarbazide
► using Sodium hydroxide
(especially for Hg2+ ion)
Hg2+ + 2OHˉ → HgO↓ + H2O
Hg2+ + 2OHˉ → HgO↓ + H2O
Elemental analysis
Слайд 34► X-ray diffraction crystallography
For Mercury complex we found the answer below
from
operator:
operator:
But the crystal structure of 1,3-bis(2-cyanophenyl)triazene
ligand was determined.
Слайд 39conclusion
► Elemental analysis & spectroscopic studies show that
two
kind of complex containing Aryltriazene & Hg cation
were formed.
► Molecular & crystal structure of
[Hg(CH3OC6H4N3C6H4OCH3)2]
were determined by X-ray diffraction method. The
complex crystallizes in Orthorhombic crystal system
& and Pna21 space group.
► Crystal structure of complex of Hg cation &
1,3-bis(2-cyanophenyl)triazene was not determined;
but studies show that the ML2 complex was formed.
were formed.
► Molecular & crystal structure of
[Hg(CH3OC6H4N3C6H4OCH3)2]
were determined by X-ray diffraction method. The
complex crystallizes in Orthorhombic crystal system
& and Pna21 space group.
► Crystal structure of complex of Hg cation &
1,3-bis(2-cyanophenyl)triazene was not determined;
but studies show that the ML2 complex was formed.
Слайд 41Special thanks to:
Dr. Mohammad R. Melardi
Dr. Mohammad K. Rofouei
Dr. Saeed Dehghanpour
Dr.
Mohammad R. Talei
Thank you . . .
