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@article{1412781,
author = {Taherzadeh, Maryam and Pourayoubi, Mehrdad and Afzali, Raheleh and Nečas, Marek},
article_location = {ABINGDON},
article_number = {8},
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},
language = {eng},
issn = {1042-6507},
journal = {Phosphorus, Sulfur, and Silicon and the related elements},
title = {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},
volume = {192},
year = {2017}
}
TY - JOUR
ID - 1412781
AU - Taherzadeh, Maryam - Pourayoubi, Mehrdad - Afzali, Raheleh - Nečas, Marek
PY - 2017
TI - 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
JF - Phosphorus, Sulfur, and Silicon and the related elements
VL - 192
IS - 8
SP - 936-944
EP - 936-944
PB - Taylor and Francis Inc.
SN - 10426507
KW - Phosphoric triamide
KW - X-ray diffraction
KW - N-H center dot center dot center dot O hydrogen bond
KW - N-HV center dot center dot center dot pi hydrogen bond
KW - DFT calculation
KW - Hirshfeld surface analysis
N2 - 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.
ER -
TAHERZADEH, Maryam, Mehrdad POURAYOUBI, Raheleh AFZALI a Marek NEČAS. 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. \textit{Phosphorus, Sulfur, and Silicon and the related elements}. ABINGDON: Taylor and Francis Inc., 2017, roč.~192, č.~8, s.~936-944. ISSN~1042-6507. Dostupné z: https://dx.doi.org/10.1080/10426507.2017.1295960.
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