RESEARCH ARTICLE

A mechanistic study of hydroboration of 1-octene with 1,3,2-dithiaborolane and 1,3,2-dithiaborinane: Part 2. A DFT study of disproportionation and hydroboration

Siphamandla W. Hadebe^I; Ross S. Robinson^I; Hendrik G. Kruger^II

^IWarren Research Laboratory, School of Chemistry, University of KwaZulu-Natal, Private Bag X01, Scottsville, Pietermaritzburg 3209, South Africa
^IISchool of Chemistry, University of KwaZulu-Natal, Private Bag X54001, Westville, Durban 4000, South Africa

ABSTRACT

The hydroboration reactions of propene with 1,3,2-dithiaborolane and 1,3,2-dithiaborinane in their ground states have been studied using density functional theory (DFT) at the B3LYP/3-21 + G and B3LYP/6-31 + G(d) levels. Hydroboration and disproportionation transition states have been determined and activation energies for these transition states were compared. It has been shown that hydroboration reactions require slightly higher activation energies than disproportionation, and yield thermodynamically more stable products.

Keywords: Hydroboration, disproportionation, DFT, transition states, potential energy surface

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Acknowledgements

Financial support from SASOL and the University of KwaZulu-Natal is gratefully acknowledged, as are Drs Arno de Klerk and Hein Strauss for collaborative involvement in this ongoing project.

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Received 2 December 2008
Revised 9 February 2009
Accepted 25 February 2009

* Present address: Fischer-Tropsch Refinery Catalysis, Sasol Technology Research and Development, P.O. Box 1, Sasolburg 1947, South Africa.
** To whom correspondence should be addressed. E-mail: robinsonr@ukzn.ac.za