Syntheses, crystal structure and ab initio calculations of two new phosphoric triamides

✍ Scribed by Kh. Gholivand; C.O. Della Vedova; A. Anaraki Firooz; A. Madani Alizadehgan; M.C. Michelini; R. Pis Diez

• Book ID: 103837090
• Publisher: Elsevier Science
• Year: 2005
• Tongue: English
• Weight: 533 KB
• Volume: 750
• Category: Article
• ISSN: 0022-2860
• DOI: 10.1016/j.molstruc.2005.04.010

✦ Synopsis

The reaction of N-benzoylphosphoramidic dichloride with piperidine and 4-methylpiperidine lead to PhC(O)N(H)P(O)R 2 with RZpiperidine (1) and RZ4-methylpiperidine (2) as N-benzoyl-N 0 ,N 00 -bis(piperidine) phosphoric triamide and N-benzoyl-N 0 ,N 00 -bis(4-methylpiperidine) phosphoric triamide, respectively. The products have been characterized by 1 H, 13 C, 31 P NMR spectra, and by elemental analysis. The crystalline solid for (1) and ( 2) consists surprisingly of four and two independent molecules, respectively. There is a disorder in one amine group due to ring inversion in each conformer in compound 1. In the solid state, comparable magnitudes for the stabilization of the stable conformers for the more or less discrete molecules, the polarization effects, hydrogen bonding and the packing effects could be anticipated.

The geometry of compound (1) optimized by density functional calculations at the B3LYP/6-31CCG* (d,p) level, is in good agreement with data obtained from X-ray crystallography.