Stacked Naphthyls and Weak
Hydrogen-Bond Interactions
Govern the Conformational Behavior of <i>P</i>‑Resolved
Cyclic Phosphonamides: A Combined Experimental and Computational Study
Maria
Annunziata M. Capozzi
Francesco Capitelli
Andrea Bottoni
Matteo Calvaresi
Cosimo Cardellicchio
10.1021/jo502094g.s004
https://acs.figshare.com/articles/dataset/Stacked_Naphthyls_and_Weak_Hydrogen_Bond_Interactions_Govern_the_Conformational_Behavior_of_i_P_i_Resolved_Cyclic_Phosphonamides_A_Combined_Experimental_and_Computational_Study/2232952
<i>P</i>-Enantiomerically
pure cyclic phosphonamides
have been synthesized via a cyclization reaction of (<i>S</i>,<i>S</i>)-aminobenzylnaphthols with chloromethylphosphonic
dichloride. The reaction is highly stereoselective and gives almost
exclusively (<i>S</i>,<i>S</i>,<i>S</i><sub>P</sub>)-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.
2014-11-21 00:00:00
Stacked Naphthyls
CH
NMR spectra
cyclization reaction
Conformational Behavior
cyclic phosphonamides
cyclization reaction forces
naphthyl rings
chlorine atoms
hydrogen bondings
QM computations
assembly
naphthyl groups
chloromethylphosphonic dichloride