Competing and directing interactions in new
phosphoramide/thiophosphoramide structures: energy
considerations and evidence for CHMIDLINE HORIZONTAL ELLIPSISHC
contacts and aliphatic-aromatic stacking

J 2023

Competing and directing interactions in new phosphoramide/thiophosphoramide structures: energy considerations and evidence for CHMIDLINE HORIZONTAL ELLIPSISHC contacts and aliphatic-aromatic stacking

HOSSEINPOOR, Saeed, Mehrdad POURAYOUBI, Mozhgan ABRISHAMI, Marjan SOBATI, Fatemeh Karimi AHMADABAD et. al.

Basic information

Original name

Competing and directing interactions in new phosphoramide/thiophosphoramide structures: energy considerations and evidence for CHMIDLINE HORIZONTAL ELLIPSISHC contacts and aliphatic-aromatic stacking

Authors

HOSSEINPOOR, Saeed, Mehrdad POURAYOUBI, Mozhgan ABRISHAMI, Marjan SOBATI, Fatemeh Karimi AHMADABAD, Fahimeh SABBAGHI, Marek NEČAS (203 Czech Republic, guarantor, belonging to the institution), Michal DUSEK, Monika KUCERAKOVA and Manpreet KAUR

Edition

CrystEngComm, Cambridge, RSC Publishing, 2023, 1466-8033

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

References:

URL

Impact factor

Impact factor: 3.100 in 2022

RIV identification code

RIV/00216224:14310/23:00132620

Organization unit

Faculty of Science

DOI

http://dx.doi.org/10.1039/d3ce00204g

UT WoS

000963972100001

Keywords in English

HYDROGEN-BOND PATTERNS; PHOSPHORIC TRIAMIDES; DATABASE ANALYSIS

Abstract

V originále

Supramolecular aggregates, driven by different molecular functionalities and crystal forces, are studied in new phosphoramide and thiophosphoramide structures (C6H5O)(2)P(O)(2-NHC5H4N) (I), (4-Cl-C6H4O)P(O)(NHC6H11)(2) (II), (4-Cl-C6H4O)P(O)(N(CH3)C6H11)(2) (III), P(S)(NHC(CH3)(3))(3) (IV), and P(S)(3-NHC5H4N)(3) (V). DHMIDLINE HORIZONTAL ELLIPSISA (D = N, C; A = N, O, S) hydrogen bonds, contacts related to the ring stacking (CHMIDLINE HORIZONTAL ELLIPSISp/sMIDLINE HORIZONTAL ELLIPSISp and pMIDLINE HORIZONTAL ELLIPSISp) and some other weak interactions are the structural elements inspected. The techniques/methods used are X-ray crystallography, QTAIM, NCI, 2D fingerprint plots, and lattice energy calculations, complemented by spectroscopic approaches for some additional investigations. A comparison is made with selected analogous structures from the Cambridge Structural Database (CSD). Determinative roles of stronger hydrogen bonds and competition between weaker hydrogen bonds (mostly having dispersion characteristics) are addressed as well as the cyclohexylMIDLINE HORIZONTAL ELLIPSISarene (sMIDLINE HORIZONTAL ELLIPSISp) stacking with pronounced CHMIDLINE HORIZONTAL ELLIPSISp interactions. When the strength and specificity of the hydrogen bonds decrease, the molecules can form a denser packing, and the role of CHMIDLINE HORIZONTAL ELLIPSISHC interactions becomes prominent. Despite their weakness, such interactions together make the bulk of the crystal stabilizing forces.

Links

LM2018127, research and development project

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

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

90242, large research infrastructures

Name: CIISB III

Citovat

HOSSEINPOOR, Saeed, Mehrdad POURAYOUBI, Mozhgan ABRISHAMI, Marjan SOBATI, Fatemeh Karimi AHMADABAD, Fahimeh SABBAGHI, Marek NEČAS, Michal DUSEK, Monika KUCERAKOVA and Manpreet KAUR. Competing and directing interactions in new phosphoramide/thiophosphoramide structures: energy considerations and evidence for CHMIDLINE HORIZONTAL ELLIPSISHC contacts and aliphatic-aromatic stacking. CrystEngComm. Cambridge: RSC Publishing, 2023, vol. 25, No 17, p. 2557-2569. ISSN 1466-8033. Available from: https://dx.doi.org/10.1039/d3ce00204g.

@article{2352422,
   author = {Hosseinpoor, Saeed and Pourayoubi, Mehrdad and Abrishami, Mozhgan and Sobati, Marjan and Ahmadabad, Fatemeh Karimi and Sabbaghi, Fahimeh and Nečas, Marek and Dusek, Michal and Kucerakova, Monika and Kaur, Manpreet},
   article_location = {Cambridge},
   article_number = {17},
   doi = {http://dx.doi.org/10.1039/d3ce00204g},
   keywords = {HYDROGEN-BOND PATTERNS; PHOSPHORIC TRIAMIDES; DATABASE ANALYSIS},
   language = {eng},
   issn = {1466-8033},
   journal = {CrystEngComm},
   title = {Competing and directing interactions in new phosphoramide/thiophosphoramide structures: energy considerations and evidence for CHMIDLINE HORIZONTAL ELLIPSISHC contacts and aliphatic-aromatic stacking},
   url = {https://pubs.rsc.org/en/content/articlelanding/2023/CE/D3CE00204G},
   volume = {25},
   year = {2023}
}

TY  - JOUR
ID  - 2352422
AU  - Hosseinpoor, Saeed - Pourayoubi, Mehrdad - Abrishami, Mozhgan - Sobati, Marjan - Ahmadabad, Fatemeh Karimi - Sabbaghi, Fahimeh - Nečas, Marek - Dusek, Michal - Kucerakova, Monika - Kaur, Manpreet
PY  - 2023
TI  - Competing and directing interactions in new phosphoramide/thiophosphoramide structures: energy considerations and evidence for CHMIDLINE HORIZONTAL ELLIPSISHC contacts and aliphatic-aromatic stacking
JF  - CrystEngComm
VL  - 25
IS  - 17
SP  - 2557-2569
EP  - 2557-2569
PB  - RSC Publishing
SN  - 14668033
KW  - HYDROGEN-BOND PATTERNS
KW  - PHOSPHORIC TRIAMIDES
KW  - DATABASE ANALYSIS
UR  - https://pubs.rsc.org/en/content/articlelanding/2023/CE/D3CE00204G
N2  - Supramolecular aggregates, driven by different molecular functionalities and crystal forces, are studied in new phosphoramide and thiophosphoramide structures (C6H5O)(2)P(O)(2-NHC5H4N) (I), (4-Cl-C6H4O)P(O)(NHC6H11)(2) (II), (4-Cl-C6H4O)P(O)(N(CH3)C6H11)(2) (III), P(S)(NHC(CH3)(3))(3) (IV), and P(S)(3-NHC5H4N)(3) (V). DHMIDLINE HORIZONTAL ELLIPSISA (D = N, C; A = N, O, S) hydrogen bonds, contacts related to the ring stacking (CHMIDLINE HORIZONTAL ELLIPSISp/sMIDLINE HORIZONTAL ELLIPSISp and pMIDLINE HORIZONTAL ELLIPSISp) and some other weak interactions are the structural elements inspected. The techniques/methods used are X-ray crystallography, QTAIM, NCI, 2D fingerprint plots, and lattice energy calculations, complemented by spectroscopic approaches for some additional investigations. A comparison is made with selected analogous structures from the Cambridge Structural Database (CSD). Determinative roles of stronger hydrogen bonds and competition between weaker hydrogen bonds (mostly having dispersion characteristics) are addressed as well as the cyclohexylMIDLINE HORIZONTAL ELLIPSISarene (sMIDLINE HORIZONTAL ELLIPSISp) stacking with pronounced CHMIDLINE HORIZONTAL ELLIPSISp interactions. When the strength and specificity of the hydrogen bonds decrease, the molecules can form a denser packing, and the role of CHMIDLINE HORIZONTAL ELLIPSISHC interactions becomes prominent. Despite their weakness, such interactions together make the bulk of the crystal stabilizing forces.
ER  -

HOSSEINPOOR, Saeed, Mehrdad POURAYOUBI, Mozhgan ABRISHAMI, Marjan SOBATI, Fatemeh Karimi AHMADABAD, Fahimeh SABBAGHI, Marek NEČAS, Michal DUSEK, Monika KUCERAKOVA and Manpreet KAUR. Competing and directing interactions in new phosphoramide/thiophosphoramide structures: energy considerations and evidence for CHMIDLINE HORIZONTAL ELLIPSISHC contacts and aliphatic-aromatic stacking. \textit{CrystEngComm}. Cambridge: RSC Publishing, 2023, vol.~25, No~17, p.~2557-2569. ISSN~1466-8033. Available from: https://dx.doi.org/10.1039/d3ce00204g.

Detailed Information on Publication Record