Original scientific paper

https://doi.org/10.5562/cca2490

Towards the Strongest Neutral Organic Superbases Based on Intramolecular H-bonds

Danijela Barić ; Quantum Organic Chemistry Group, Division of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička 54, 10000 Zagreb, Croatia
Borislav Kovačević ; Quantum Organic Chemistry Group, Division of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička 54, 10000 Zagreb, Croatia

Abstract

Utilizing several different trialkylarsine oxides and substituted pyridine N-oxides as a hydrogen bond acceptors in tri-substituted guanidines we designed several very basic superbases possessing intramo-lecular hydrogen bonds (IHB-superbases), with proton affinity in the gas phase that comes very close to that of paradigmatic P4-tBu Schwesinger superbase and with pKa in acetonitrile up to 36
units.

Keywords

organic superbases; intramolecular hydrogen bonds; DFT calculations

Hrčak ID:

131547

URI

https://hrcak.srce.hr/131547

Publication date:

22.12.2014.

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