O-Phenyl (tert-butylamido)(p-tolylamido)phosphinate

Abstract

In the title mol­ecule, C17H23N2O2P, the P atom has a distorted tetra­hedral environment. The P—N bond to the tolyl­amido fragment is 1.642 (4) Å while that to the butyl­amido fragment is 1.629 (3) Å. The dihedral angle between the two benzene rings is 82.3 (2)°. In the crystal, adjacent mol­ecules are linked via weak N—H⋯(O)P and N—H⋯N hydrogen-bonding inter­actions into an extended chain parallel to the b axis. The three methyl groups of the tert-butyl­amido substituent are disordered over two sets of sites with equal occupancies. The crystal studied was found to be a non-merohedral twin with the minor twin component = 23.1 (1)%.

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

“…In compounds (I), (II) and (III), the P atom exhibits a distorted tetrahedral environment, as has been noted for other amidophosphoesters Pourayoubi, Rheingold et al, 2011). In (I), the angles at the P atom are in the range 94.80 (7)-116.36 (7) .…”

“…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.…”

“…[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.] The systematic study of such molecules may be useful for: (i) gaining insight into the reason why a particular amide group makes a stronger or weaker P-N bond; (ii) the preparation of racemic compounds ; (iii) finding new synthesis and purification procedures (Pourayoubi, Rheingold et al, 2011); (iv) comparison of the hydrogen-bond patterns for finding empirical rules to predict hydrogen-bond patterns based on molecular structure (Toghraee et al, 2011;Pourayoubi et al, 2012).…”

“…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.]…”