jo502094g_si_004.cif (17.61 kB)
Stacked Naphthyls and Weak Hydrogen-Bond Interactions Govern the Conformational Behavior of P‑Resolved Cyclic Phosphonamides: A Combined Experimental and Computational Study
dataset
posted on 2014-11-21, 00:00 authored by Maria
Annunziata M. Capozzi, Francesco Capitelli, Andrea Bottoni, Matteo Calvaresi, Cosimo CardellicchioP-Enantiomerically
pure cyclic phosphonamides
have been synthesized via a cyclization reaction of (S,S)-aminobenzylnaphthols with chloromethylphosphonic
dichloride. The reaction is highly stereoselective and gives almost
exclusively (S,S,SP)-cyclic phosphonamides in good yields. Analysis of the
X-ray crystal structures shows clearly that the cyclization reaction
forces the two naphthyl rings into a stable parallel displaced stacking
assembly and indicates also the existence of intramolecular CH···π
interactions and weak forms of intermolecular hydrogen bondings, involving
the oxygen and the chlorine atoms. QM computations and NMR spectra
in solution confirm the stacked molecular assembly as the preferred
arrangement of the two naphthyl groups.