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

Author

Danijela Barić and Borislav Kovačević

Subjects
chemistry.chemical_compound, Chemistry, Hydrogen bond, Intramolecular force, Superbase, Pyridine, Proton affinity, General Chemistry, Photochemistry, Acetonitrile, organic superbases, intramolecular hydrogen bonds, DFT calculations, Gas phase
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.

Published
2014

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