Synthesis, spectral, X-ray diffraction and DFT studies on 1-(2-methyl-2-propenyl)-3-(2,3,4,5,6-pentamethylbenzyl)benzimidazolium chloride hydrate

ABSTRACT

A new benzimidazole based N-heterocyclic carbene (NHC) salt (1) was synthesized by the reaction of benzimidazole precursor with alkyl halide. The structure of 1 was determined by elemental analysis, FT-IR, ¹H NMR and ¹³C NMR spectroscopy tecniques and X-ray crystallography. The compound crystallized in the triclinic space group P-1 with two molecules in the unit cell. The optimization of 1 was firstly performed at B3LYP/6-311G++(d,p) level, then the theoretical spectral studies performed and compared with the experimental values. Besides the frontier molecular orbital energies and chemical reactivity analysis of 1, together with the electrostatic potential and molecular electrostatic potential analyses were performed at the same level of theory.

KEYWORDS:

• DFT calculations
• N-Heterocyclic carbene
• X-ray diffraction
• ¹H and ¹³C NMR

Acknowledgements

The authors acknowledge the Scientific and Technological Research of Turkey (TÜBITAK-BIDEB), the National Research Fellow-ship Programme for grants to N. Ş., Amasya University, Turkey, for the use of the Gaussian09W program and Ondokuz Mayıs University, Turkey, for the use of the STOE IPDS 2 diffractometer (purchased under grant F.279 of the University Research Fund).