Volume 33, Issue 1 (3-2025)
www.ijcm.ir 2025, 33(1): 161-168 |
Back to browse issues page
Download citation:
BibTeX | RIS | EndNote | Medlars | ProCite | Reference Manager | RefWorks
Send citation to:
BibTeX | RIS | EndNote | Medlars | ProCite | Reference Manager | RefWorks
Send citation to:
Khorramaki M, Pourayoubi M, Poupon M. Synthesis and crystal structure study of a new single-enantiomer phosphinicamide, (C6H5)2P(O)[NH-(S)-(–)CH(CH3)(C6H4-4-CH3)]: Hirshfeld surface analysis. www.ijcm.ir 2025; 33 (1) :161-168
URL: http://ijcm.ir/article-1-1909-en.html
URL: http://ijcm.ir/article-1-1909-en.html
1- Department of Chemistry, Faculty of Science, Ferdowsi University of Mashhad, Mashhad, Iran
2- Institute of Physics of the Czech Academy of Science, Na Slovance 2, 182 21 Prague 8, Czech Republic
2- Institute of Physics of the Czech Academy of Science, Na Slovance 2, 182 21 Prague 8, Czech Republic
Abstract: (327 Views)
In this research, the preparation of single crystal X-ray diffraction analysis of a new chiral compound of N-(1-paratolyl(ethyl))-P,P-diphenylphosphinicamide, (C6H5)2P(O)[NH-(S)-(–)CH(CH3)(C6H4-4-CH3)] are reported. This compound is crystallized in the orthorhombic crystal system with chiral space group , Z = 4, a = 23.400 (5) Å, b = 13.870 (3) Å and c = 11.301 (2) Å. The asymmetric unit consists of two symmetry-independent phosphinicamide molecules, which show the greatest difference in the N—C—C—C torsion angles related to the chiral amine. In the crystal structure, a three-dimensional arrangement of molecules is created by the N—H…O═P, C—H…O═P and C—H…π hydrogen bonds. The Hirshfeld surface (HS) analysis and two-dimensional fingerprint plots were studied to investigate the interactions in the structure. The ultraviolet absorption and rotational circular dichroism spectra were measured.
Keywords: Phosphinicamide, Crystal Structure, Single-Enantiomer, Hirshfeld Surface Analysis, Fingerprint Plots.
References
1. [1] Prins L.J., Reinhoudt D.N., Timmerman, P., ''Noncovalent Synthesis Using Hydrogen Bonding'', Angewandte Chemie International Edition 40 (2001) 2382-2426.
https://doi.org/10.1002/1521-3773(20010702)40:13<2382::AID-ANIE2382>3.0.CO;2-G [DOI:10.1002/1521-3773(20010702)40:133.0.CO;2-G]
2. [2] Gu B., Zhao C., Baev A., Yong K-T., Wen S., Rasad P.N., ''Molecular Nonlinear Optics : Recent Advances and Applications'', Advances in Optics and Photonics 8 (2016) 328-369. [DOI:10.1364/AOP.8.000328]
3. [3] Zinna F., Giovanella U., Di Bari L., ''Highly Circularly Polarized Electroluminescence from a Chiral Europium Complex'', Advanced Materials Letters 27 (2015) 1791-1795. [DOI:10.1002/adma.201404891]
4. [4] Headley C.E., Marsden S.P., ''Synthesis and Application of P-Stereogenic Phosphines as Superior Reagents in the Asymmetric Aza-Wittig Reaction'', Journal of Organic Chemistry 72 (2007) 7185-7189. [DOI:10.1021/jo0709908]
5. [5] Hua D.H., Chan-yu-king R., Mckie J.A., ''Chiral Allylphosphonyl Anions (Ambident Nucleophiles) with Cyclic Enones (Ambident Electrophiles)'', Journal of the American Chemical Society 109 (1987) 5026-5029. [DOI:10.1021/ja00250a047]
6. [6] De Luca L., Chiminazzo A., Sperni L., Strukul G., Scarso A., ''Stereoselective Synthesis of Chiral Isatin Containing Bisphosphonates as Potential Anti-Resorption Bone Drugs'', ChemistrySelect 2 (2017) 3262-3267. [DOI:10.1002/slct.201700649]
7. [7] Bredikhin A.A., Gubaidullin A.T., Bredikhina Z.A., Krivolapov D.B., Pashagin A.V., Litvinov I.A., ''Absolute Configuration and Crystal Packing for Three Chiral Drugs Prone to Spontaneous Resolution: Guaifenesin, Methocarbamol and Mephenesin'', Journal of Molecular Structure 920 (2009) 377-382. [DOI:10.1016/j.molstruc.2008.11.037]
8. [8] Nakayama K., Thompson W.J., ''A Highly Enantioselective Synthesis of Phosphate Triesters'', Journal of the American Chemical Society 112 (1990) 6936-6942. [DOI:10.1021/ja00175a030]
9. [9] Karimi Ahmadabad F., Pourayoubi M., Bakhshi H., ''Decorated Single-Enantiomer Phosphoramide-Based Silica/magnetic Nanocomposites for Direct Enantioseparation'', RSC Advances 9 (2019) 27147-27156. [DOI:10.1039/C9RA03260F]
10. [10] Eslami F., Pourayoubi M., Sabbaghi F., Skořepová E., Dušek M., Baniyaghoob S., ''Diastereotopic Groups in Two New Single- Enantiomer Structures (R)2P(O)[NH-(+)CH(C2H5)(C6H5)] (R = OC6H5 and C6H5)'', Acta Crystallographica Section E, Crystallographic Communications 79 (2023) 769-776. [DOI:10.1107/S2056989023006278]
11. [11] Warren T.K., Jordan R., Lo M.K., Ray A.S., Mackman R.L., Soloveva V., Siegel D., Perron M., Bannister R., Hui H.C., Larson N., Strickley R., Wells J., Stuthman K.S., Van Tongeren S.A., Garza N.L., Donnelly G., Shurtleff A.C., Retterer C.J., Gharaibeh D., Grimes E., Welch L.S., Gomba L., Wilhelmsen C.L., Zamani R., Kenny T., Brett P., Nichols D.K., Nuss J.E., Nagle E.R., Kugelman J.R., Palacios G., Doerffler E., Neville S., Carra E., Clarke M.O., Zhang L., Lew W., Ross B., Wang Q., Chun K., Wolfe L., Babusis D., Park Y., Stray K.M., Trancheva I., Feng J.Y., Barauskas O., Xu Y., Wong P., Braun M.R., Flint M., Mcmullan L.K., Chen S., Fearns R., Swaminathan S., Mayers D.L., Spiropoulou C.F., Lee W.A., Nichol S.T., Cihlar T., Bavari S., ''Therapeutic Efficacy of the Small Molecule GS-5734 Against Ebola Virus in Rhesus Monkeys'', Nature 531 (2016) 381-385. [DOI:10.1038/nature17180]
12. [12] Palacios F., ''Synthesis of -Aminophosphonates and -Phosphinates'', Chemical Reviews 105 (2005) 899-931. [DOI:10.1021/cr040672y]
13. [13] Nguyen C., Kim J., ''Thermal Stabilities and Flame Retardancies of Nitrogen - Phosphorus Flame Retardants Based on Bisphosphoramidates'', Polymer Degradation and Stability 93 (2008) 1037-1043. [DOI:10.1016/j.polymdegradstab.2008.03.024]
14. [14] Aladzheva I.M., Bykhovskaya O.V., Nelyubina Y.V., Klemenkova Z.S., Petrovskii P.V., Odinets I.L., ''Uranium Complexes of Cyclic O,O-bidentate Ligands With the P-N-P Backbone'', Inorganica Chimica Acta 373 (2011) 130-136. [DOI:10.1016/j.ica.2011.04.007]
15. [15] Spackman M.A., Jayatilaka D., ''Hirshfeld Surface Analysis'', CrystEngComm 11 (2009) 19-32. [DOI:10.1039/B818330A]
16. [16] Sheldrick G.M., ''Crystal Structure Refinement With SHELXL'', Acta Crystallographica Section C: Structural Chemistry 71 (2015) 3-8. [DOI:10.1107/S2053229614024218]
17. [17] Sheldrick G.M., ''SHELXT-Integrated Sspace-Group and Crystal-Structure Determination'', Acta Crystallographica Section A: Foundations and Advances 71 (2015) 3-8. [DOI:10.1107/S2053273314026370]
18. [18] Hamzehee F., Pourayoubi M., Farhadipour A., Choquesillo-Lazarte D., ''Two New Phosphinic Amides: Synthesis, Crystal Structure, and Theoretical Study of Hydrogen Bonding'', Phosphorus, Sulfur, and Silicon and the Related Elements 192 (2017) 359-367. [DOI:10.1080/10426507.2016.1239200]
19. [19] Corbridge D.E.C., Phosphorus-An outline of its chemistry, biochemistry, and technology, Boca Raton 2013.
20. [20] Spackman P.R., Turner M.J., McKinnon J.J., Wolff S.K., Grimwood D.J., Jayatilaka D., Spackman M.A., ''CrystalExplorer : a Program for Hirshfeld Surface Analysis, Visualization and Quantitative Analysis of Molecular Crystals'', Journal of Applied Crystallography 54 (2021) 1006-1011. [DOI:10.1107/S1600576721002910]
21. [21] McKinnon J.J., Jayatilaka D., Spackman M.A., ''Towards Quantitative Analysis of Intermolecular Interactions With Hirshfeld Surfaces'', Chemical Communications 37 (2007) 3814-3816. [DOI:10.1039/b704980c]
Send email to the article author
| Rights and permissions | |
 |
This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License. |
