TAHERZADEH, Maryam, Mehrdad POURAYOUBI, Raheleh AFZALI and 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. Phosphorus, Sulfur, and Silicon and the related elements. ABINGDON: Taylor and Francis Inc., 2017, vol. 192, No 8, p. 936-944. ISSN 1042-6507. Available from: https://dx.doi.org/10.1080/10426507.2017.1295960.
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Basic information
Original 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
Authors TAHERZADEH, Maryam (364 Islamic Republic of Iran), Mehrdad POURAYOUBI (364 Islamic Republic of Iran), Raheleh AFZALI (364 Islamic Republic of Iran) and Marek NEČAS (203 Czech Republic, guarantor, belonging to the institution).
Edition Phosphorus, Sulfur, and Silicon and the related elements, ABINGDON, Taylor and Francis Inc. 2017, 1042-6507.
Other information
Original language English
Type of outcome Article in a journal
Field of Study 10402 Inorganic and nuclear chemistry
Country of publisher United Kingdom of Great Britain and Northern Ireland
Confidentiality degree is not subject to a state or trade secret
Impact factor Impact factor: 0.674
RIV identification code RIV/00216224:14310/17:00100507
Organization unit Faculty of Science
Doi http://dx.doi.org/10.1080/10426507.2017.1295960
UT WoS 000409328300007
Keywords in English 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
Tags NZ, rivok
Tags International impact, Reviewed
Changed by Changed by: Ing. Nicole Zrilić, učo 240776. Changed: 12/4/2018 13:43.
Abstract
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.
Links
LM2015043, research and development projectName: Česká infrastruktura pro integrativní strukturní biologii (Acronym: CIISB)
Investor: Ministry of Education, Youth and Sports of the CR
LQ1601, research and development projectName: CEITEC 2020 (Acronym: CEITEC2020)
Investor: Ministry of Education, Youth and Sports of the CR
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