Theoretical Investigation Non-covalent Interactions of N-(diphenylphosphinothioyl)-2-pyrazinecarboxamide
DOI:
https://doi.org/10.29356/jmcs.v68i2.1936Keywords:
Phosphine chalcogenide, Non-covalent interaction, NCI analysis, Hirshfeld, QTAIM, NBOAbstract
Abstract. Phosphine chalcogenides can form reliable and reproducible supramolecular synthons through noncovalent interactions that can be employed for designing high dimensional supramolecular architectures. Here, we systematically study the influence of non-covalent interactions in the fabrication of these synthons and the stability of the crystalline structure of (N2C4H3)C(O)NHP(S)(C6H5)2 (1) through non-covalent interactions (NCI) analysis, molecular Hirshfeld surfaces and the corresponding two-dimensional (2D) fingerprint plots. The theoretical studies were employed to further confirm the presence of these synthons by comparing the stabilization energies of the dimers and monomers. The nature and electronic structure of the phosphor-chalcogenid bond in (N2C4H3)C(O)NHP(E)(OC6H5)2(E = S(1), O(2), and Se (3)) have also been evaluated by QTAIM, NBO, MEP, and HOMO-LUMO energy gaps.
Resumen. Los calcogenuros de fosfina pueden formar sintones moleculares confiables y reproducibles por medio de interacciones nocovalentes que se pueden utilizar para diseñar arquitecturas supramoleculares de alta dimensionalidad. En este trabajo estudiamos sistemáticamente la influencia de las interacciones nocovalentes en la preparación de estos sintones y en la estabilidad de la estructura cristalina de N2C4H3)C(O)NHP(S)(C6H5)2 (1), usando el análisis NCI de interacciones nocovalentes, las superficies moleculares de Hirshfeld y sus correspondientes gráficas bidimensionales (2D). Los estudios teóricos se usaron para confirmar la presencia de estos sintones al comparar las energías de estabilización de los dímeros y monómeros. La naturaleza y estructura electrónica del enlace fósforo-calcogenuro en (N2C4H3)C(O)NHP(E)(OC6H5)2(E = S(1), O(2), y Se (3)) también se estudiaron con QTAIM, NBO, MEP y el gap de energía HOMO-LUMO.
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Mirzaei, M.; Eshghi, H.; Akhlaghi Bagherjeri, F.; Mirzaei, M.; Farhadipour, A. J. Mol. Struct. 2018, 1163, 316-326. DOI: https://doi.org/10.1016/j.molstruc.2018.03.014
Desiraju, G. R. Angew. Chem. Int. Edit. 1995, 34, 2311-2327. DOI: https://doi.org/10.1002/anie.199523111
Desiraju, G. R. in: The Design of Organic Solids: Elsevier: Amsterdam, 1989.
Desiraju, G. R. Angew. Chem. Int. Edit. 2007, 46, 8342–8356. DOI: https://doi.org/10.1002/anie.200700534
Seth, S. K.; Bauza, A.; Frontera, A. Cryst. Eng. Comm. 2018, 20, 746-754. DOI: https://doi.org/10.1039/C7CE01991B
Khavasi, H. R.; Gholami, A.; Hosseini, M.; Nikpoor, L.; Eskandari, K. Cryst. Growth. Des. 2020, 20, 2266-2274. DOI: https://doi.org/10.1021/acs.cgd.9b01385
Ray Choudhury, S.; Gamez, P.; Robertazzi, A.; Chen, C.Y.; Lee, H. M.; Mukhopadhyay, S. Cryst. Growth. Des. 2008, 8, 3773-3784. DOI: https://doi.org/10.1021/cg800403p
Sathiyaraj, E.; Thirumaran, S.; Selvanayagam, S.; Sridhar, B.; Ciattini, S. J. Mol. Struct. 2018, 1159, 156-166. DOI: https://doi.org/10.1016/j.molstruc.2018.01.038
Mitra, M.; Manna, P.; Bauza, A.; Ballester, P.; Seth, S-k.; Choudhury, S. R.; Frontera, A.; Mukhopadhyay, S. J. Phys. Chem. B. 2014, 118, 14713-14726. DOI: https://doi.org/10.1021/jp510075m
Gholivand, K.; Hosseini, M.; Ebrahimi Valmoozi, A. A.; Farshadfar, K. Cryst. Eng. Comm. 2017, 19, 2536-2548. DOI: https://doi.org/10.1039/C7CE00039A
Khavasi, H. R.; AzhdariTehrani, A. Inorg. Chem. 2013, 52, 2891–2905. DOI: https://doi.org/10.1021/ic3021113
Metrangolo, P.; Resnati, G. in: Halogen bonding, fundamentals and applications, Springer. 2008. DOI: https://doi.org/10.1007/978-3-540-74330-9
Piltan, M.; Farshadfar, K.; Mark Roe, S. Eur. J. Inorg. Chem. 2017, 2017, 2723-2726. DOI: https://doi.org/10.1002/ejic.201700369
(a) Khavasi, H. R.; Azizpoor Fard, M. Cryst. Growth. Des. 2010, 10, 1892-1896. (b) Field J. S.; Munro, Q. Q.; Waldron, B. P. Dalton. Trans. 2012, 41, 5486−5496. (c) He, L.; Ma, D.; Duan, L.; Wei, Y.; Qiao, J.; Zhang, D.; Dong, G.; Wang, L.; Qiu, Y. Inorg. Chem. 2012, 51, 4502−4510. (d) Derikvand, Z.; Azadbakht, A.; AmiriRudbari, H. J. Inorg. Organomet. Polym. Mater. 2019, 29, 502–516.
(a) Janssen, F. F. B. J.; Gelde, R. G. Rowan, A. E. Cryst. Growth. Des. 2011, 11, 4326−4333. (b) Tiekink, E. R. T.; Zukerman-Schpector, J. Cryst.Eng. Comm. 2009, 11, 1176-1186. (c) Hay, B. P.; Bryantsev, V. S. Chem. Commun. 2008, 2417−2428. (d) Mooibroek, T. J.; Gamez, P.; Reedijk, J. Cryst. Eng. Comm. 2008, 10, 1501−1515. (e) Schottel, B. L.; Chifotides, H. T.; Dunbar, K. R. Chem. Soc. Rev. 2008, 37, 68−83. (f) Orvay, F.; Bauza, A.; Barcelo-Oliver, M.; Raso, A. G.; Fiol, J. J.; Costa, A.; Molins, E.; Mata, E.; Frontera, A. Cryst. Eng. Comm. 2014, 16, 9043-9053.
Popescu, A. P.; Laromaine, A.; Teixidor, F.; Sillanpaa, R.; Kivekas, R.; Liambias, J. I.; Vinas, C. Chem. Eur. J. 2011, 17, 4429 - 4443. DOI: https://doi.org/10.1002/chem.201003330
Davies, R. in: Chalcogen-phosphorus (and heavier congeners) chemistry, Chapter 5 of handbook of chalcogen chemistry, RSC Publishing, 2007. DOI: https://doi.org/10.1039/9781847557575-00286
(a) Cook, J. B.; Nicholson, B. K.; Smith, D. W. J. Organomet. Chem. 2004, 689, 860-869 (b) Chutia, P.; Kumari, N.; Sharma, M.; Woollins, J. D.; Slawin, A. M. Z.; Dutta, D. K. Polyhedron. 2004, 23, 1657-1661.
Glueck, D. S. Chem. Eur. J. 2008, 14, 7108 - 7117. DOI: https://doi.org/10.1002/chem.200800267
(a) Koh, W. K.; Yoon,Y.; Murray, C. B. Chem. Mater. 2011, 23, 1825-1829. (b) Evans, C. M.; Evans, M. E.; Krauss, T.D. J. Am. Chem. Soc. 2010, 132, 10973-10975. (c) Liu, H.; Owen, J. S.; Alivisatos, A. P. J. Am. Chem. Soc. 2007, 129, 305-312. (d) Arachchige, I. U.; Brock, S. L. Acc. Chem. Res. 2007, 40, 801 - 809.
(a) Gholivand, K.; Madani Alizadehgan, A.; Mojahed, F.; Soleimani, P. Polyhedron. 2008, 27, 1639-1649 (b) Gholivand, K.; Shariatinia, Z.; Mashhadi, S. M.; Daeepour, F.; Farshidnasab, N.; Mahzouni, H.R.; Taheri, N.; Amiri, S.; Ansar, S. Polyhedron. 2009, 28, 307–321. (c) Shi, M.; Shi, J. W. Tetrahedron: Asymmetry. 2007, 18, 645–650.
Gholivand, K.; Gholami, A.; Ebrahimi, A. A. V.; Abolghasemi, S. T.; Esrafili, M. D.; Fadaei, F. T.; Schenk, K. J. Rsc. Adv. 2015, 5, 17482-17492. DOI: https://doi.org/10.1039/C4RA12925C
Gholivand, K.; Farshadian, S.; Hosseini, Z.; Khajeh, K.; Akbari, N. Appl. Organomet. Chem. 2010, 24, 700–707. DOI: https://doi.org/10.1002/aoc.1669
(a) Eini Roumiani, M.; Dorosti,N. Ultrason. Sonochem. 2019, 55, 207-216. (b) Nikpour, S.; Dorosti, N.; Afshar, F.; Kubicki, M. Appl. Organomet. Chem. 2020, e5724. (c) Gholivand, K.; Hosseini, Z.; Farshadian, S.; Naderi Manesh, H. Eur. J. Med. Chem. 2010, 45, 5130-5139. DOI: https://doi.org/10.1016/j.ejmech.2010.08.025
Manna, P.; Ray Choudhury, S.; Mitraa, M.; Seth, S.K.; Helliwell, M.; Bauza, A.; Frontera, A.; Mukhopadhyay, S. A. J. Solid. State. Chem. 2014, 220, 149-156. (b) Mirzaei, M.; Eshtiagh-Hosseini, H.; Karrabi, Z.; Notash, B.; Bauza, A.; Frontera, A.; Habibi, M.; Ardalani, M.; Shamsipur, M.; J. Mol. Stru. 2015, 1079, 78-86.
(a) Gholivand, K.; Hosseini, M.; Maghsoud, Y.; Valenta, J.; Ebrahimi Valmuzi, A.A.; Owczarzak, A.; Kubicki, M.; Jamshidi, M.; Kahnouji, M. Inorg. Chem. 2019, 58, 9, 5630–5645. (b) Gholivand, K.; Farshadfar, K.; Roe, S.M.; Hosseini, M.; Gholami, A. Cryst. Eng. Comm.2016, 18, 7104-7115. DOI: https://doi.org/10.1021/acs.inorgchem.8b03611
Dorosti, N.; Nikpour, S.; Molaei, F.; Kubicki, M. Chem. Pap. 2021, 75, 2503-2516. DOI: https://doi.org/10.1007/s11696-020-01461-2
Gholivand, K.; Dorosti, N. Monatsh. Chem. 2013, 144, 1417-1425. DOI: https://doi.org/10.1007/s00706-013-0960-4
Alvarado, S. R.; Shortt, I. A.; Fan, H. I.; Vela, J. Organometallics. 2015, 34, 4023-4031. DOI: https://doi.org/10.1021/acs.organomet.5b00428
Yanai, T.; Tew, D. P.; Handy, N. C. Chem. Phys. Lett. 2004, 393, 51–57. DOI: https://doi.org/10.1016/j.cplett.2004.06.011
Boys, S. F.; Bernardi, F. Mol. Phys.1970, 19, 553–566. DOI: https://doi.org/10.1080/00268977000101561
Bader, R. F. W. Chem. Rev.1991, 91, 893-928. DOI: https://doi.org/10.1021/cr00005a013
Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev.1988, 88, 899–926. DOI: https://doi.org/10.1021/cr00088a005
Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, M. A.; Robb, J. R.; Cheeseman, G.;et al. Gaussian 09, Revision D.01. Gaussian, Inc. Wallingford, 2009.
Johnson, E. R.; Keinan, S.; Mori-Sanchez, P.; Contreras-Garcia, J.; Cohen, A. J.; Yang, W. J. Am. Chem. Soc. 2010, 132, 6498–6506. DOI: https://doi.org/10.1021/ja100936w
Lu, T.; Chen, F. J. Theor. Comput. Chem. 2012, 11, 163-183. DOI: https://doi.org/10.1142/S0219633612500113
Humphrey, W.; Dalke, A.; Schulten, K. J. Mol. Graphics.1996, 14, 33–38. DOI: https://doi.org/10.1016/0263-7855(96)00018-5
Wolff, S. K.; Grimwood, D. J.; McKinnon, J. J.; Turner, M. J.; Jayatilaka, D.; Spackman, M. A. Crystalexplorer 3.0, University of Western Australia, Perth, Australia, 2012.
Spackman, M. A.; McKinnon, J. J. Cryst. Eng. Comm. 2002, 4, 378–392. DOI: https://doi.org/10.1039/B203191B
Nishio, M. Cryst. Eng. Comm. 2004, 6, 130–158. DOI: https://doi.org/10.1039/b313104a
Nishio, M. Phys. Chem. Chem. Phys. 2011, 13, 13873–13900. DOI: https://doi.org/10.1039/c1cp20404a
(a) Umezawa, Y.; Tsuboyama, S.; Takahashi, H.; Uzawa, J.; Nishio, M. Tetrahedron. 1999, 5, 10047–10056. (b) Mirdya, S.; Roy, S.; Chatterjee, S.; Bauza, A.; Frontera, A.; Chattopadhyay, S. Cryst. Growth. Des. 2019, 19, 5869-5881.
Kim, K. S.; Tarakeshwar, P.; Lee, J. Y. Chem. Rev. 2000, 100, 4145-4185. DOI: https://doi.org/10.1021/cr990051i
(a) Gabriele, S.; Gatti, C.; Lo Presti, L.; Garcia, J. C. Chem. Eur. J. 2012, 18, 15523–15536. (b) Lande, D. N.; Bhadane, S. A.; Gejji, S. P. J. Phys. Chem. 2017, 121, 1814–1824.
Spackman, M. A.; Byrom, P. G. Chem. Phys. Lett. 1997, 267, 215–220. DOI: https://doi.org/10.1016/S0009-2614(97)00100-0
Gholivand, K.; Azadbakht, M.; Maghsoud, Y.; Hosseini, M. J. Organomet. Chem. 2019, 879, 27-39. DOI: https://doi.org/10.1016/j.jorganchem.2018.10.012
Taghizadeh, L.; Montazerozohori, M.; Masoudiasl, A.; Joohari, S.; White, J. M. Mater. Sci. Eng. C. 2017, 77, 229–244. (b) Bejaoui, C.; Ameur, I.; Derbel, N.; Linden, A.; Abid, S. J. Mol. Struct. 2018, 1166, 7-14. (c) Binzet, G.; Gumus, I.; Dogen, A.; Florke, U.; Kulku, N.; Arslan, H. J. Mol. Struct. 2018, 1161, 519-529.
Politzer, P.; Murray, J. S. Theor. Chem. Acc. 2002, 108, 134–142 DOI: https://doi.org/10.1007/s00214-002-0363-9
(a) Gholivand, K.; Mahzouni, H. R.; Pourayoubi, M.; Amiri, S. Inorg. Chim. Acta. 2010, 363, 2318–2324. (b) Gholivand, K.; Oroujzadeh, N.; Afshar, F. J. Organomet. Chem. 2010, 695, 1383–1391. (c) Torabi Farkhani, E.; Pourayoubi, M.; Izadyar, M.; Andreev, P. V.; Shchegravina, E. S. Dalton. Trans. 2019, 48, 17908-17918. (d) Taherzadeh, M.; Pourayoubi,M.; Nečas, M. Phosphorus. Sulfur. 2019, 194, 39-46.
Bader, R. F. W. Oxford University Press, New York, 1990.
Dobado, J. A.; Martínez-García, H.; Molina, J.M.; Sundberg, M. R. J. Am. Chem. Soc.1998, 120, 33, 8461-8471. DOI: https://doi.org/10.1021/ja980141p
Jamroz, M. H. in: Vibrational energy distribution analysis, VEDA 4 computer program, Poland, 2004.
Zhou, Z.; Navangul, H. V. J. Phys. Org. Chem. 1990, 3, 784-788. DOI: https://doi.org/10.1002/poc.610031203
Senet, P. Chem. Phys. Lett. 1997, 275, 527-532. DOI: https://doi.org/10.1016/S0009-2614(97)00799-9
Sarıoz, O.; Oznergiz, S.; Kandemirli, F. Syn. React. Inorg. Met. Org. Chem. 2013, 43, 185–195.
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