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, 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.

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

• 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
• WWW: 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
• Tags: CF BIC, rivok
• Tags: International impact, Reviewed

Abstract

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