CRYSTAL AND MOLECULAR-STRUCTURE OF 2 N-CHALCOGENOPHOSPHORYL-CHALCOGENOUREAS

Ph(Me)N-C(O)-NH-P(O)(OPh)2, 1, and Ph(Me)N-C(S)-NH-P(S)(OPh)2, 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 P1-N1-C1-N2 sequence is observed. P1-N1 bonds (1: 1.646, 1.646 A; 2:: 1.671 Å), N1-C1 bonds (1: 1.406, 1.397 Å 2: 1.378 Å) and N2-C1 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). © 1991, Taylor & Francis Group, LLC. All rights reserved.