N,N′-Dicyclohexyl-N′′-(4-nitrobenzoyl)phosphoric triamide

Abstract

The P atom in the title compound, C19H29N4O4P, exhibits a tetra­hedral coordination and the phosphoryl and carbonyl groups are anti to each other. Adjacent mol­ecules are linked by N—H⋯O hydrogen bonds to form a layer motif.

N,N′-Dibenzyl-N′′-(2-chloro-2,2-difluoroacetyl)-N,N′-dimethylphosphoric triamide

“…The P═O bond length is comparable to those in similar compounds e.g. in P (Sabbaghi et al, 2010). In the (CClF 2 )C(O) unit, the O-C-C-F dihedral angles showing the orientation of flourine atoms relative to carbonyl group are 17.7 (3) and 137.1 (2)° and the O-C-C-Cl dihedral angle is -101.9 (2)°.…”

“…For phosphoric triamide compounds having a C( O)NHP( O) skeleton, see: Pourayoubi & Sabbaghi (2009) and references cited therein. For bond lengths in related structures, see: Sabbaghi et al (2010). For hydrogenbond motifs, see: Etter et al (1990); Bernstein et al (1995).…”

Different orientations of C=O versus P=O in P(O)NHC(O) skeleton: the first study on an aliphatic diazaphosphorinane with a gauche orientation

“…Infrared (IR) spectra were recorded on a Buck 500 scientific spectrometer using KBr disc. 4-F-C 6 [7].…”

“…This is in agreement with the previously reported diazaphosphorinane compounds [26] and compounds with cyclic five-and six-membered ring amide groups linked to P atom, and in contrast with the reported acyclic amides such as N(CH 2 CH 3 ) 2 and N(CH 2 CH 3 )(CH 2 C 6 H 5 ) which show 2 J(P,C) [ 3 J(P,C) [27] (NR 1 R 2 is introduced as an amide moiety, where R 1 and/or R 2 are H, alkyl, or aryl). Moreover, in the 4-F-C 6 Compound 1 with a gauche orientation of C=O versus P=O shows a deshielded carbon atom of carbonyl moiety relative to that of 2 (167.67 ppm for 1 and 166.85 ppm for 2). This is supported by IR spectroscopy in which a lower C=O frequency is observed for 1 (1636 vs 1656 cm -1 for 2).…”

“…The anti orientation is preferred for the C=O versus P=O unit [6,7]. Some researchers have employed the anionic form [P(O)NC(O)] -to obtain compounds with a non-anti orientation [8] and better donority properties [9].…”