Two new thiophosphoramide structures: N,N′,N′′‐tricyclohexylphosphorothioic triamide and O,O′‐diethyl (2‐phenylhydrazin‐1‐yl)thiophosphonate |
| |
Authors: | Mehrdad Pourayoubi Mozhgan Abrishami Vclav Eigner Marek Ne
as Michal Duek Mahmoud Delavar |
| |
Abstract: | The compound N,N′,N′′‐tricyclohexylphosphorothioic triamide, C18H36N3PS or P(S)NHC6H11]3, (I), crystallizes in the space group Pnma with the molecule lying across a mirror plane; one N atom lies on the mirror plane, whereas the bond‐angle sum at the other N atom has a deviation of some 8° from the ideal value of 360° for a planar configuration. The orientation of the atoms attached to this nonplanar N atom corresponds to an anti orientation of the corresponding lone electron pair (LEP) with respect to the P=S group. The P=S bond length of 1.9785 (6) Å is within the expected range for compounds with a P(S)N]3 skeleton; however, it is in the region of the longest bond lengths found for analogous structures. This may be due to the involvement of the P=S group in N—H...S=P hydrogen bonds. In O,O′‐diethyl (2‐phenylhydrazin‐1‐yl)thiophosphonate, C10H17N2O2PS or P(S)OC2H5]2NHNHC6H5], (II), the bond‐angle sum at the N atom attached to the phenyl ring is 345.1°, whereas, for the N atom bonded to the P atom, a practically planar environment is observed, with a bond‐angle sum of 359.1°. A Cambridge Structural Database CSD; Allen (2002). Acta Cryst. B 58 , 380–388] analysis shows a shift of the maximum population of P=S bond lengths in compounds with a P(S)O]2N] skeleton to the shorter bond lengths relative to compounds with a P(S)N]3 skeleton. The influence of this difference on the collective tendencies of N...S distances in N—H...S hydrogen bonds for structures with P(S)N]3 and P(S)O]2N] segments were studied through a CSD analysis. |
| |
Keywords: | crystal structure thiophosphoramide database analysis P(S)[O]2[N] skeleton phosphorothioic triamide P(S)[N]3 skeleton N— H S hydrogen bond NMR experiment |
|
|