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X-ray Structural Confirmation of Conformationally Biased Ketones

In a collaboration with the Woerpel group at NYU, graduate student Alexandra Dillon and Research Professor Tony Hu captured 2-chloropropiophenone in a hydrogen-bonded host framework generated from guanidinium and 4,4’-biphenyldisulfonate ions to produce a crystalline inclusion compound, which permitted the determination of the conformation of the 2-chloropropiophenone guest with single crystal X-ray diffraction. The observed conformation corroborated the stereoselectivity observed upon nucleophilic attack by allylmagnesium halide at the most accessible diastereoface of the lowest-energy conformations of the ketone. Find the article here.