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RESEARCH ARTICLE
Contents Vol 68(1)

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

Kishor Naktode A , Sayak Das Gupta A , Abhinanda Kundu A , Salil K. Jana A , Hari Pada Nayek B , Bhabani S. Mallik A C and Tarun K. Panda A C
+ Author Affiliations
- Author Affiliations

A Department of Chemistry, Indian Institute of Technology Hyderabad, Ordnance Factory Estate, Yeddumailaram 502205, Andhra Pradesh, India.

B Department of Applied Chemistry, Indian School of Mines, Dhanbad, 826004, Jharkhand, India.

C Corresponding authors. Email: bhabani@iith.ac.in; tpanda@iith.ac.in

Australian Journal of Chemistry 68(1) 127-136 https://doi.org/10.1071/CH14078
Submitted: 18 February 2014  Accepted: 14 April 2014   Published: 6 June 2014

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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