Electronic aspects of hydrogen bond patterns of P=O center dot center dot center dot H in crystal structures of phosphoramido acid derivatives: QSAR study of anti-urease activity, Hirshfeld surface analysis, and DFT calculations

摘要

New derivatives of phosphoramido acid with the formula(C6H11NCH3)(NHCOCF3)P(O)(O-)(CH3-+NH2-C6H11)(1) (amidophosphoricacid), (C6H5)(2)P(O)(O-)(+NH3-C6H4-NH2)(2) (phosphonicacid), (C6H5O)(2)P(O)(O-)(+NH3-C6H4-NH2) (3) (phosphoricacidester) were synthesized and characterized by X-ray crystallography. The asymmetric unit of compounds 1-3 consists of one molecule with the P atom in a tetrahedral environment. The X-ray structural analysis showed that the H-bond patterns depend on the kind of atoms linked to the P atom. In the crystal packing of compound 1, P(O)center dot center dot center dot H-N and C(O)center dot center dot center dot H-N hydrogen bonds in 3 and P(O)center dot center dot center dot H-N distances in compounds 2 and 3 led to a one-dimensional arrangement. The energy of P-O center dot center dot center dot H-N hydrogen bond (E-HB) model and stabilizing energies (E-2) were calculated. Hirshfeld surface analysis demonstrated that the C center dot center dot center dot H contact is attributed to CH center dot center dot center dot pi contact in the 2 and 3 compounds and the F center dot center dot center dot H contact is referred to hydrogen bond in one O center dot center dot center dot H counterion interaction. Quantitative structure-activity relationship (QSAR) was used to comprehend the relationship between molecular structural features and the inhibitory of investigated compounds. The use of density functional theory along with the QSAR model for enzymes revealed the importance of Q(H) parameter in describing the anti-AChE and anti-urease activities of monophosphoramidates including P(O)-NH2 moiety.