Functionalisation of Imidazolin-2-imine to Corresponding Phosphinamine, Chalcogenide (O, S, Se, Te), and Borane Compounds

Naktode, K and Gupta, S D and Kundu, A and Jana, S K and Nayek, H P and Mallik, Bhabani Shankar and Panda, Tarun K (2015) Functionalisation of Imidazolin-2-imine to Corresponding Phosphinamine, Chalcogenide (O, S, Se, Te), and Borane Compounds. Australian Journal of Chemistry, 68 (1). pp. 127-136. ISSN 0004-9425

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Abstract

1,3-Di-tert-butyl-imidazolin-2-ylidine-1,1-diphenylphosphinamine (2) was prepared from 1,3-di-tert-butyl-imidazolin-2-imine (1) and chlorodiphenylphosphine. Compound 2 was treated further with elemental sulfur, selenium, and tellurium to afford the corresponding chalcogenide derivatives, 1,3-di-tert-butyl-imidazolin-2-ylidine-P,P-diphenyl-phosphinothioicamide (4), 1,3-di-tert-butyl-imidazolin-2-ylidine-P,P-diphenyl-phosphinoselenoicamide (5), and 1,3-di-tert-butyl-imidazolin-2-ylidine-P,P-diphenyl-phosphinotelluroicamide (6) in good yield. 1,3-Di-tert-butyl-imidazolin-2-ylidine-P,P-diphenylphosphinicamide (3) was obtained by dissolving compound 2 in hydrochloric acid solution in THF. The corresponding borane adduct, 1,3-di-tert-butyl-imidazolin-2-ylidine-P,P-diphenyl-phosphinaminoborane (7) was isolated by the reaction of compound 2 and sodium borohydride in good yield. The molecular structures of compounds 2 and 4–7 were established by X-ray diffraction analyses. To analyse the electronic structure of chalcogenides of imidazolin-2-imine ligands, the protonation energies of the oxygen, sulfur, and selenide derivative of ligand 2 were calculated by means of density functional theory. Finally, the charge distribution in compounds 3, 4, and 5 were determined using natural bond orbital analysis.

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IITH Creators:
IITH CreatorsORCiD
Mallik, Bhabani Shankarhttp://orcid.org/0000-0001-9657-1497
Panda, Tarun Khttp://orcid.org/0000-0003-0975-0118
Item Type: Article
Subjects: Chemistry
Divisions: Department of Chemistry
Depositing User: Library Staff
Date Deposited: 09 Mar 2015 11:36
Last Modified: 07 Sep 2017 10:54
URI: http://raiithold.iith.ac.in/id/eprint/1379
Publisher URL: https://doi.org/10.1071/CH14078
OA policy: http://www.sherpa.ac.uk/romeo/issn/0004-9425/
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