Informace o publikaci

The first C(O)NHP(O)-based phosphoric triamide structure with an N-H...pi hydrogen bonding: A combination of X-ray crystallography and theoretical study to evaluate the strength of hydrogen bonds



Rok publikování 2017
Druh Článek v odborném periodiku
Časopis / Zdroj Phosphorus, Sulfur, and Silicon and the related elements
Fakulta / Pracoviště MU

Přírodovědecká fakulta

Klíčová slova Phosphoric triamide; X-ray diffraction; N-H center dot center dot center dot O hydrogen bond; N-HV center dot center dot center dot pi hydrogen bond; DFT calculation; Hirshfeld surface analysis
Popis The hydrogen bond pattern of N-(4-methoxybenzoyl)-N',N''-bis(4-methylbenzyl)-phosphoric triamide, C24H28N3O3P, (I), was investigated. In the crystal structure, the molecules are aggregated through N-CP-HO=P and N-P-HO=C hydrogen bonds in a one-dimensional arrangement parallel to the c axis (N-CP is the nitrogen atom in the C(O)NHP(O) segment and N-P stands for the two other nitrogen atoms bonded to the P atom). There is also a novel N-P-H pi hydrogen bond in the crystal which extends the aggregation of the molecules to a two-dimensional array parallel to the bc plane. A Cambridge Structural Database (CSD, version 5.37, Feb 2016) analysis shows that the N-H pi hydrogen bond was not observed in any of 156 [RC(O)NH]P(O)[NR1R2](2) ](2) (R-1 not equal H, R-2 = H or not equal H) phosphoric triamide structures reported so far. The theoretical calculations at the B3LYP/6-311G** level of theory (DFT, AIM, and NBO) were performed to evaluate the strengths of N-CP-HO-P, NP-HO-C and NP-Hp hydrogen bonds, considering two-aggregate molecular assemblies containing these hydrogen bonds. The calculations on the title compound suggest that the intermolecular NCP-HO-P hydrogen bond is stronger than NP-HO-C and NP-Hp interactions. The hydrogen bond strength was investigated by NBO, topological analysis, geometry calculation, Hirshfeld surface analysis and experimental spectroscopic results, which are in agreement with each other.
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