DL-Diethyl α-anilinobenzylphosphonate

N–H···O=P hydrogen-bonded dimers as the main structural motif of aminophosphonate diesters

“…3). Geometrical parameters for the examined aminophosphonates are in a good agreement with those of the related compounds (Table S1 in Supplementary material) [17,18,28,29]. Differences in the bond lengths or angles for these structures are within the three standard deviations, while the torsion angles differ for 8°.…”

“…In addition, the phosphoryl oxygen also forms the interaction with the neighboring aromatic C-H donor functionality of an inversion-related molecule. According to the literature data, described hydrogen-bonded dimers are preferred structural motif in majority of aminophosphonate diester compounds [1,[17][18][19]29]. The dimer formation was not observed in compounds where P=O and N-H groups are not in the synperiplanar position [38,39].…”

Syntheses, characterization, stereochemistry and complexing properties of acyclic and macrocyclic compounds possessing ?-amino- or ?-hydroxyphosphonate units: a review article

“…The geometry adopted in the solid state by derivative Ia (X ‫ס‬ Y ‫ס‬ H) was investigated by X-ray diffraction [10,11], and the following salient characteristics were found:…”

“…The pair of chiral methyne carbon atoms gives rise to the formation of S,S and R,R enantiomers in the solid state that are tightly bound together by O-H-N bridges [10]. Considering that the biological activity of chiral compounds depends on the absolute configuration, as reported in several literature examples [12,2a,2d], we developed a direct and efficient enantioselective resolution of some of the phosphonates Ia-If using commercially available HPLC chiral columns [13,14].…”

Associative vs. dissociative mechanism of P-C bond breaking in α-aminophosphonates leading to phosphoric acid [P(V)] derivatives.

“…For example 1-(N-phenylamino)-1-phenyl-methylphosphonic acid was analysed by Ruźić-Toruś. 34 In the case of α-aminophosphonates there are two centers of basicity, the amine nitrogen and the phosphoryl oxygen. 35 We have performed calculations of the possible equilibria that could exist in α-aminophosphonates 36,37 and we have found that the presence of a basic amine group in close proximity to the phosphoryl oxygen helps in protonation of the latter by the neighboring group effect.…”