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
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216224%3A14310%2F17%3A00100507" target="_blank" >RIV/00216224:14310/17:00100507 - isvavai.cz</a>
Result on the web
<a href="http://dx.doi.org/10.1080/10426507.2017.1295960" target="_blank" >http://dx.doi.org/10.1080/10426507.2017.1295960</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1080/10426507.2017.1295960" target="_blank" >10.1080/10426507.2017.1295960</a>
Alternative languages
Result language
angličtina
Original language name
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
Original language 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.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10402 - Inorganic and nuclear chemistry
Result continuities
Project
Result was created during the realization of more than one project. More information in the Projects tab.
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Others
Publication year
2017
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Phosphorus, Sulfur, and Silicon and the related elements
ISSN
1042-6507
e-ISSN
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Volume of the periodical
192
Issue of the periodical within the volume
8
Country of publishing house
GB - UNITED KINGDOM
Number of pages
9
Pages from-to
936-944
UT code for WoS article
000409328300007
EID of the result in the Scopus database
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