Stacked naphthyls and weak hydrogen bond interactions govern the conformational behavior of P-resolved cyclic phosphonamides: a combined experimental and computational study

Torna indietro

Abstract

P-enantiomerically pure cyclic phosphonamides have been synthesized via a cyclisation 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 cyclisation reaction forces the two naphthyl rings into a stable parallel displaced stacking assembly and indicates also the existence of intra-molecular CH…pi interactions and weak forms of inter-molecular 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.

Autore Pugliese

Tutti gli autori

  • CAPOZZI M.A.M.

Titolo volume/Rivista

Non Disponibile

Anno di pubblicazione

2014

ISSN

0022-3263

ISBN

Non Disponibile

Numero di citazioni Wos

6

Ultimo Aggiornamento Citazioni

Non Disponibile

Numero di citazioni Scopus

6

Ultimo Aggiornamento Citazioni

Non Disponibile

Settori ERC

Non Disponibile

Codici ASJC

Non Disponibile