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

Warning

This publication doesn't include Faculty of Economics and Administration. It includes Faculty of Science. Official publication website can be found on muni.cz.
Authors

TAHERZADEH Maryam POURAYOUBI Mehrdad AFZALI Raheleh NEČAS Marek

Year of publication 2017
Type Article in Periodical
Magazine / Source Phosphorus, Sulfur, and Silicon and the related elements
MU Faculty or unit

Faculty of Science

Citation
Doi http://dx.doi.org/10.1080/10426507.2017.1295960
Keywords 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
Description 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.
Related projects:

You are running an old browser version. We recommend updating your browser to its latest version.