O-Phenyl (cyclohexylamido)(p-tolylamido)phosphinate

Abstract

In the title mol­ecule, C19H25N2O2P, the P atom is bonded in a distorted tetra­hedral environment. The dihedral angle between the two phenyl rings is 89.09 (8)°. The methyl H atoms are disordered over two sets of sites with equal occupancy. The O atom of the P=O group acts as a double hydrogen-bond acceptor of the type (N—H)2⋯(O=)P—, forming R 2 2(8) rings which are further linked into chains along [010].

Newrac-XP(O)(OC6H5)(NHC6H4-p-CH3) [X= N(CH3)(cyclo-C6H11) and NH(C3H5)] andrac-(C6H5CH2NH)P(O)(OC6H5)(NH-cyclo-C6H11) mixed-amide phosphinates

“…Moreover, the hybridization of the C atom attached to the N atom in the p-tolylamido group is different from those of the N-methylcyclohexylamido and allylamido groups (sp 2 and sp 3 ). This is in accord with what was reported for rac-LP(O)(OC 6 H 5 )-(NHC 6 H 4 -p-CH 3 ) [L = NHC 6 H 11 (Sabbaghi et al, 2011), NHC(CH 3 ) 3 (Pourayoubi, Rheingold et al, 2011) and NHCH 2 C 6 H 5 ]. The P-N (p-tolylamido) bond is also longer than the related P-N (L) bond.…”

“…As has been noted in the literature Pourayoubi, Rheingold et al, 2011;Sabbaghi et al, 2011), the p-toluidine hydrochloride salt is relatively insoluble in CH 3 CN and also in CHCl 3 (although the degree of solubility can be affected by the other starting materials used in the preparation method). The reaction of C 6 H 5 OP(O)Cl 2 and p-CH 3 -C 6 H 4 NH 2 (1:2 molar ratio) was performed in CH 3 CN (at ice-bath temperature), the [p-CH 3 -C 6 H 4 NH 3 ]Cl by-product was simply filtered off and the racemic product ClP(O)(OC 6 H 5 )(NHC 6 H 4 -p-CH 3 ) was obtained from the solution.…”

“…Up to now, this racemic starting compound has been used for the preparation of rac-LP(O)(OC 6 H 5 )(NHC 6 H 4 -p-CH 3 ) [L = NHC 6 H 11 (Sabbaghi et al, 2011), NHC(CH 3 ) 3 (Pourayoubi, Rheingold et al, 2011) and NHCH 2 C 6 H 5 ]. Here, we used the abovementioned starting racemic compound to study the syntheses and crystal structures of rac-phenyl (N-methylcyclohexylamido)(p-tolylamido)phosphinate, (I) (Fig.…”

“…Recently, the syntheses and diffraction experiments were described for some racemic mixed-amide phosphinates having an (N 1 )P( O)(O)(N 2 ) skeleton, where two different amide groups are bonded to the P atom Pourayoubi, Rheingold et al, 2011;Sabbaghi et al, 2011). [In compounds with a P(O)(NR 1 R 2 ) segment, the NR 1 R 2 group obtained from an NHR 1 R 2 amine is named as an amido group.]…”

Syntheses and structures of four new mixed-amide phosphoric triamides

“…After completion of the reaction, the [R 1 R 2 NH 2 ]Cl byproduct is removed by filtration (Pourayoubi et al, 2013;Sabbaghi et al, 2011;Ghadimi et al, 2009). It should be mentioned that, although H 2 O is usually used for removing [R 1 R 2 NH 2 ]Cl salts in the preparation of compounds such as phosphoric triamides (which do not include phosphorushalogen bonds), it could not be used for removing the [R 1 R 2 NH 2 ]Cl by-product in the purification of the phosphorus-chlorine reagent.…”