Elimination of Ethene from 1,2-Diiodoethane Induced by N-Heterocyclic Carbene Halogen Bonding

Poynder, Tiffany; Savaliya, Dharmeshkumar P; Molino, Andrew; Wilson, David; Dutton, Jason

doi:10.26181/607fb25b1df34

Tiff_SN2_revise.docx (505.57 kB)

Elimination of Ethene from 1,2-Diiodoethane Induced by N-Heterocyclic Carbene Halogen Bonding

journal contribution

posted on 2021-04-21, 05:04 authored by Tiffany Poynder, Dharmeshkumar P Savaliya, Andrew MolinoAndrew Molino, David WilsonDavid Wilson, Jason DuttonJason Dutton

The attempted synthesis of N-heterocyclic carbene (NHC)-stabilised dicarbon (C ) fragments via nucleophilic substitution at 1,2-diiodoethane is reported. Rather than the expected S 2 pathway, clean elimination of ethene and formation of an iodoimidazolium cation was observed. The resistance towards nucleophilic substitution piqued interest, and subsequent investigation determined NHC-halogen bonding as the source. This is in contrast to reactions between NHCs and other alkyl halides, where substitution or elimination pathways are reported. A detailed theoretical study between these cases highlights the importance of iodine as a halogen bond donor compared with other halogens, and shows that NHCs are excellent halogen bond acceptors. This reactivity suggests potential for application of the halogen bonding interaction between NHCs and organic compounds. 2 N

Funding

The authors thank The La Trobe Institute for Molecular Science for their generous funding of this project. This work was also supported by an ARC Future Fellowship (JLD, FT16010007). Generous allocation of computing resources from National Computational Infrastructure (NCI), Intersect, and La Trobe University are acknowledged.

History

Publication Date

2019-01-01

Journal

Australian Journal of Chemistry

Volume

72

Issue

8

Pagination

(p. 614-619)

Publisher

CSIRO

ISSN

0004-9425

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