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Abstract
Ph(Me)N[sbnd]C(O)[sbnd]NH[sbnd]P(O)(OPh)2, 1, and Ph(Me)N[sbnd]C(S)[sbnd]NH[sbnd]P(S)(OPh)Z, 2, were synthesized by reaction of N-methyl aniline with (PhO)2P(O)NCO and (PhO)2P(S)NCS, respectively. X-ray crystal structure analysis shows that 1 crystallizes in space group Pna21 with two symmetry-independent molecules, 2 in space group P1. In both compounds 1 and 2 an extended π-delocalization along the Pl[sbnd]N1[sbnd]Cl[sbnd]N2 sequence is observed. P1[sbnd]N1 bonds (1: 1.646, 1.646 A; 2:: 1.671 Å), Nl[sbnd]Cl bonds (1: 1.406, 1.397 Å; 2: 1.378 Å) and N2[sbnd]Cl bonds (1: 1.358 Å, 1.360 Å; 2: 1.354 Å) are remarkably shorter than single bonds. Configurations of the molecules are Z,E' for 1 and Z,Z' for 2. 1 forms in the crystal dimers with NH … O hydrogen bonds via phosphoryl oxygen (N … O distances 2.863 Å, 2.891 Å).
