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

Abstract

The mixed-amide phosphinates, rac-phenyl (N-methylcyclohexylamido)(p-tolylamido)phosphinate, C20H27N2O2P, (I), and rac-phenyl (allylamido)(p-tolylamido)phosphinate, C16H19N2O2P, (II), were synthesized from the racemic phosphorus-chlorine compound (R,S)-(Cl)P(O)(OC6H5)(NHC6H4-p-CH3). Furthermore, the phosphorus-chlorine compound ClP(O)(OC6H5)(NH-cyclo-C6H11) was synthesized for the first time and used for the synthesis of rac-phenyl (benzylamido)(cyclohexylamido)phosphinate, C19H25N2O2P, (III). The strategies for the synthesis of racemic mixed-amide phosphinates are discussed. The P atom in each compound is in a distorted tetrahedral (N(1))P(=O)(O)(N(2)) environment. In (I) and (II), the p-tolylamido substituent makes a longer P-N bond than those involving the N-methylcyclohexylamido and allylamido substituents. In (III), the differences between the P-N bond lengths involving the cyclohexylamido and benzylamido substituents are not significant. In all three structures, the phosphoryl O atom takes part with the N-H unit in hydrogen-bonding interactions, viz. an N-H···O=P hydrogen bond for (I) and (N-H)(N-H)···O=P hydrogen bonds for (II) and (III), building linear arrangements along [001] for (I) and along [010] for (III), and a ladder arrangement along [100] for (II).

Syntheses and structures of four new mixed-amide phosphoric triamides

“…Recently, we have investigated the syntheses and crystal structures of racemic mixed-amide phosphinates having an (N 1 )P( O)(OC 6 H 5 )(N 2 ) segment, where N 1 and N 2 belong to two different -NR x R y groups (R x 6 ¼ H; R y = H or 6 ¼ H) (Pourayoubi et al, , 2013.…”

“…Racemic Cl(R 1 R 2 N)P(O)(OC 6 H 5 ) phosphorus-chlorine reagents [NR 1 R 2 = NH(cyclo-C 6 H 11 ) and NH(C 6 H 4 -4-CH 3 )] were used in reactions with different amines (Pourayoubi et al, , 2013. In these reactions, the most challenging tasks are related to the synthesis of the racemic Cl(R 1 R 2 N)P(O)-(OC 6 H 5 ) phosphorus-chlorine compounds [from the commercial (C 6 H 5 O)P(O)Cl 2 reagent and two molar equivalents of the amine NHR 1 R 2 ] and then separation of the racemic reagent from the [R 1 R 2 NH 2 ]Cl alkyl/aryl ammonium chloride by-product.…”

“…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.…”

Decorated single-enantiomer phosphoramide-based silica/magnetic nanocomposites for direct enantioseparation

“…The structures investigated include both achiral and chiral phosphorus compounds. 63,[67][68][69][70] With this background in mind, in the current article, we synthesized chiral phosphoramide enantiomers including Si-OCH 3 segment in the achiral moiety, which is sensitive to hydrolysis condensation. This characteristic helps to immobilize silicon-based chiral phosphoric triamide (PTA) on Fe 3 -O 4 @SiO 2 , to produce composite materials which dually possess the chiral and superparamagnetic properties.…”

C˭O···π Interaction: A Rare Noncovalent Binding in RC(O)NHP(O)[NR1R2]2 Phosphoric Triamide Structures

“…3 The focus of our work is study of phosphoramides structures and the CSD analysis of different structural features of phosphoramides such as noncovalent interactions, especially hydrogen bonds. [4][5][6][7] In this work, we present the analysis of lone pair…π (C═O…π and P═O…π) interactions …”