Презентация на тему Islamic Azad University- Karaj Branch Faculty of Science Department of Chemistry Subject: Synthesis, Separation and Spectroscopic and Structural study.

Презентация на тему Презентация на тему Islamic Azad University- Karaj Branch Faculty of Science Department of Chemistry Subject: Synthesis, Separation and Spectroscopic and Structural study., предмет презентации: Разное. Этот материал содержит 41 слайдов. Красочные слайды и илюстрации помогут Вам заинтересовать свою аудиторию. Для просмотра воспользуйтесь проигрывателем, если материал оказался полезным для Вас - поделитесь им с друзьями с помощью социальных кнопок и добавьте наш сайт презентаций ThePresentation.ru в закладки!

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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 Hg cations

Thesis advisor:
Mohammad R. Melardi; Ph.D.
Consulting advisor:
Mohammad K. Rofouei; Ph.D.

By:
Mohammad Barkhi


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Triazenes
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


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Application of Triazenes

◘ In medicine

◘ Poisonous Cations & Anions such as Mercury, Cadmium,
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


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◘ 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.


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Properties 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).


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Preparation 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).


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The 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


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N1,N3-bidentate ligand

[Hg(N3(Ph(OCH3))2)(Cl)]

M. R. Melardi; Analytical Sciences 2007


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N1,N3-bidentate bridging ligand


[Pd(PhN3C4H8N3Ph)]2

Estela dos Reis Crespan 2005


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N1,N3-tridentate bridging ligand

[Tl(RC6H4N3C6H4R)]2

Inorganica Chimica Acta 2006


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N1,N3-tetradentate bridging ligand

[Tl(NO2C6H4N3C6H4NO2)]2

Estela dos Reis Crespan 2005


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Preparation 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…


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Experimental . . .


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1,3-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.


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Mercury complex preparation

Hg (s) + Hg2+ (aq)

[Hg2]2+(aq)

M.p= 122- 127 °C
M.w= 713.15 g.mol-1
Yield= 39.43 %

L= 1,3-bis(2-methoxyphenyl)triazene

Inorganica Chimica Acta 2007


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Elemental 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↓


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►IR spectra

Ligand

Complex

3352

1623

393

Spectroscopic studies


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►1H-NMR spectra

Ligand

Complex


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►13C-NMR spectra

Ligand

Complex


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Molecular structure of Mercury complex


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ORTEP view of Mercury complex


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Crystal packing fragment along a crystal axes


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Crystal data for Mercury complex


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(I)

(II)

[Hg(N3(Ph(OCH3))2)(Cl)]

[Hg(RC6H4N3C6H4R)2Py]


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1,3- 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 %


Single crystals in diethylether were obtained.


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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 %


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Mercury identification in complex

► using diphenylcarbazide

► using Sodium hydroxide (especially for Hg2+ ion)
Hg2+ + 2OHˉ → HgO↓ + H2O

Elemental analysis


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► UV-Visible spectra

Spectroscopic studies


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► IR spectra

Ligand

Complex

2233

3222

1604

2213


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► 1H-NMR spectra

Ligand

Complex


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► 13C-NMR spectra

Ligand

Complex


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► X-ray diffraction crystallography

For Mercury complex we found the answer below from
operator:

But the crystal structure of 1,3-bis(2-cyanophenyl)triazene
ligand was determined.


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Centrosymmetric H-bonded dimmers of molecules of type A & A'.


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General view of molecule of type A & A'.


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Stacking interaction between molecules of type A & A‘.


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Crystal packing of 1,3-bis(2-cyanophenyl)triazene


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conclusion

► 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.


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Special thanks to:

Dr. Mohammad R. Melardi
Dr. Mohammad K. Rofouei
Dr. Saeed Dehghanpour
Dr. Mohammad R. Talei

Thank you . . .


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