• PDF / 614,858 Bytes
• 6 Pages / 612 x 792 pts (letter) Page_size
• 51 Downloads / 239 Views

DOWNLOAD

REPORT

---

ynthesis and Molecular Structure Study of New Organotellurium and Organomercury Compounds Based on 4-Bromonaphthalen-1-amine R. H. Al-Asadia,* a

Department of Chemistry, College of Education for Pure Sciences, Basrah University, Basrah, 61004 Iraq *e-mail: [email protected] Received July 2, 2020; revised August 18, 2020; accepted September 21, 2020

Abstract—The new organic derivatives of mercury and tellurium have been prepared by a reaction of 4-bromonaphthalen-1-amine with Hg(CH3COO)2 and further with TeBr4. Reaction of (1-amino-4-bromonaphthalen-2-yl)mercury(II) chloride with benzaldehyde then TeBr4 has produced the new aryaltellurium(IV) tribromide containing the azomethine moiety. Reaction of 4-bromo-2-(tribromo-λ4-tellanyl)naphthalen-1-amine with 4-hydroxyphenyl mercury(II) chloride gives asymmetrical diaryaltellurium(IV) dibromide. Reduction of aryaltellurium tribromide and diaryaltellurium dibromide by hydrazine hydrate leads to the corresponding diaryalditelluride and diaryaltullride. Structures of the synthesized compounds have been elucidated from FT-IR, 1H, and 13C NMR spectra. The molecular structures and energies for the compounds were also calculated according to the DFT concept. Keywords: organotellurium, organomercury, DMol3, molecular structure, density functional theory

DOI: 10.1134/S1070363220090236 Tellurium and mercury organic compounds are characterized by high nucleophilic reactivity, biological activity and applications in synthetic organic chemistry [1–4]. Organotellurium compounds demonstrate strong antioxidant action, antitumor, anticancer and pharmaceutical activities [5–10]. Aromatic organotellurium compounds that contained electron donor nitrogen atom at ortho position to tellurium atom, such as amine, azo and azomethine groups [11–13] are characterized by high stability due to the intramolecular overlap of tellurium and nitrogen atoms [14, 15]. A series of organotellurium compounds was synthesized by tansmetallation reaction of organomercury compounds [16–18]. Organomercury(II) derivatives were efficiently used in synthesis of organometallic compounds of transition metals that were inaccessible via the Grignard or lithiation reactions [19]. Calculations based on density functional theory (DFT) have been efficiently used for a wide range of organotellurium compounds [20, 21]. The present study targeted preparation of some new mercury and tellurium organic compounds, and study of their structural and energy features using quantum chemical methods.

RESULTS AND DISCUSSION The current work is devoted to synthesis of new tellurated and mercurated compounds. Compound 1 was synthesized with high yield by the reaction of 4-bromonaphthalen-1-amine with mercuric acetate, and then with sodium chloride. Intermediate 1 reacted with tellurium tetrabromide to give aryl ortho-tellurium(IV) tribromide 2. Asymmetrical diaryl dibromotelluride 4 was formed in the reaction of compound 2 with 4-hydroxyphenyl mercury(II) chloride. A new organomercury compound containing the azomethine group 6 was forme