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

J 2017

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

TAHERZADEH, Maryam, Mehrdad POURAYOUBI, Raheleh AFZALI and Marek NEČAS

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

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10402 Inorganic and nuclear chemistry

Country of publisher

United Kingdom of Great Britain and Northern Ireland

Confidentiality degree

není předmětem státního či obchodního tajemství

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

Abstract

V originále

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 project

Name: Česká infrastruktura pro integrativní strukturní biologii (Acronym: CIISB)

Investor: Ministry of Education, Youth and Sports of the CR

LQ1601, research and development project

Name: CEITEC 2020 (Acronym: CEITEC2020)

Investor: Ministry of Education, Youth and Sports of the CR

Citovat

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.

@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 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. \textit{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.

Detailed Information on Publication Record