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Molecular Physics
An International Journal at the Interface Between Chemistry and Physics
Volume 121, 2023 - Issue 14
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Research Article

Intermolecular interactions involving the N-heterocyclic carbene and its heavier analogues C2H4N2X: (X = C, Si, Ge, Sn, Pb) with YH3F (Y = Si, Ge, Sn, Pb)

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Article: e2211906 | Received 15 Jan 2023, Accepted 04 May 2023, Published online: 12 May 2023

References

  • S.E. Wheeler, T.J. Seguin, Y. Guan, and A.C. Doney, Acc. Chem. Res. 49, 1061–1069 (2016). doi:10.1021/acs.accounts.6b00096.
  • N. Vallavoju and J. Sivaguru, Chem. Soc. Rev. 43, 4084–4101 (2014). doi:10.1039/c3cs60471c.
  • V. Georgakilas, J.N. Tiwari, K.C. Kemp, J.A. Perman, A.B. Bourlinos, K.S. Kim, and R. Zboril, Chem. Rev. 116, 5464–5519 (2016). doi:10.1021/acs.chemrev.5b00620.
  • S. Scheiner, Hydrogen Bonding. A Theoretical Perspective (Oxford University Press, New York, 1997).
  • A. Bauzá, T.J. Mooibroek, and A. Frontera, Angew. Chem. Int. Ed. 52, 12317–12321 (2013). doi:10.1002/anie.201306501.
  • J.M. Chehayber, S.T. Nagy, and C.S. Lin, Can. J. Chem. 62, 27–31 (1984). doi:10.1139/v84-006.
  • A. Bauzá, T.J. Mooibroek, and A. Frontera, Chem. Rec. 16, 473–487 (2016). doi:10.1002/tcr.201500256.
  • I. Alkorta, I. Rozas, and J. Elguero, J. Phys. Chem. A. 105, 743–749 (2001). doi:10.1021/jp002808b.
  • A.C. Legon, Phys. Chem. Chem. Phys. 19, 14884–14896 (2017). doi:10.1039/C7CP02518A.
  • S. Scheiner, Phys. Chem. Chem. Phys. 23, 5702–5717 (2021). doi:10.1039/D1CP00242B.
  • P.R. Varadwaj, A. Varadwaj, H.M. Marques, and K. Yama-shita, CrystEngComm. 25, 1411–1423 (2023). doi:10.1039/D2CE01621D.
  • T. Clark, M. Hennemann, J.S. Murray, and P. Politzer, J. Mol. Model. 13, 291–296 (2007). doi:10.1007/s00894-006-0130-2.
  • J.S. Murray, P. Lane, and P. Politzer, J. Mol. Model. 15, 723–729 (2009). doi:10.1007/s00894-008-0386-9.
  • A. Bundhun, P. Ramasami, J.S. Murray, and P. Politzer, J. Mol. Model. 19, 2739–2746 (2013). doi:10.1007/s00894-012-1571-4.
  • S.J. Grabowski, Phys. Chem. Chem. Phys. 16, 1824–1834 (2014). doi:10.1039/C3CP53369G.
  • S.A.C. McDowell and J.A. Joseph, Phys. Chem. Chem. Phys. 16, 10854–10860 (2014). doi:10.1039/c4cp01074d.
  • J.S. Murray, P. Lane, T. Clark, K.E. Riley, and P. Politzer, J. Mol. Model. 18, 541–548 (2012). doi:10.1007/s00894-011-1089-1.
  • W. Zierkiewicz, M. Michalczyk, and S. Scheiner, Molecules. 23, 1416 (2018). doi:10.3390/molecules23061416.
  • W. Li, Y. Zeng, X. Li, Z. Sun, and L. Meng, Phys. Chem. Chem. Phys. 18, 24672–24680 (2016). doi:10.1039/C6CP03713E.
  • M.X. Liu, Q.Z. Li, W.Z. Li, and J.B. Cheng, Struct. Chem. 28, 823–831 (2017). doi:10.1007/s11224-016-0890-y.
  • J.E.D. Bene, I. Alkorta, and J. Elguero, J. Phys. Chem. A. 121, 8136–8146 (2017). doi:10.1021/acs.jpca.7b08393.
  • L.H. Yang and H.M. Wang, ChemSusChem. 7, 962–998 (2014). doi:10.1002/cssc.201301131.
  • J.E.D. Bene, I. Alkorta, and J. Elguero, J. Phys. Chem. A. 121, 4039–4047 (2017). doi:10.1021/acs.jpca.7b03405.
  • I. Alkorta, M.M. Montero-Campillo, and J. Elguero, Chem.-Eur. J. 23, 10604–10609 (2017). doi:10.1002/chem.201701444.
  • M.M. Montero-Campillo, I. Alkorta, and J. Elguero, Phys. Chem. Chem. Phys. 20, 19552–19559 (2018). doi:10.1039/C8CP03217C.
  • S.J. Grabowski, Molecules. 23, 1183 (2018). doi:10.3390/molecules23051183.
  • D. Mani and E. Arunan, J. Phys. Chem. A. 118, 10081–10089 (2014). doi:10.1021/jp507849g.
  • Y.S. Chen, L.F. Yao, and F. Wang, J. Mol. Model. 27, 110 (2021). doi:10.1007/s00894-021-04738-9.
  • Y.S. Chen, L.F. Yao, and F. Wang, J. Mol. Model. 25, 351 (2019). doi:10.1007/s00894-019-4206-1.
  • J.R. Zhang, Q.Z. Hu, Q.Z. Li, S. Scheiner, and S.F. Liu, Int. J. Quantum Chem. 119, e25910 (2019). doi:10.1002/qua.25910.
  • I. Alkorta and J. Elguero, J. Heterocyclic Chem. 56, 359–370 (2019). doi:10.1002/jhet.3331.
  • A.J.I.I.I. Arduengo, M. Kline, J.C. Calabrese, and F. Davidson, J. Am. Chem. Soc. 113, 9704–9705 (1991). doi:10.1021/ja00025a063.
  • A.J.I.I.I. Arduengo, H.V.R. Dias, J.C. Calabrese, and F. Davidson, J. Am. Chem. Soc. 114, 9724–9725 (1992). doi:10.1021/ja00050a098.
  • D. Bourissou, O. Guerret, F.P. Gabbaï, and G. Bertrand, Chem. Rev. 100, 39–91 (2000). doi:10.1021/cr940472u.
  • V. Nesterov, D. Reiter, P. Bag, P. Frisch, R. Holzner, A. Porzelt, and S. Inoue, Chem. Rev. 118, 9678–9842 (2018). doi:10.1021/acs.chemrev.8b00079.
  • M. Jabłoński and M. Palusiak, Phys. Chem. Chem. Phys. 11, 5711–5719 (2009). doi:10.1039/b901968e.
  • Y.S. Chen, L.F. Yao, and F. Wang, Comput. Theor. Chem. 1220, 114020 (2023). doi:10.1016/j.comptc.2023.114020.
  • M. Asay, C. Jones, and M. Driess, Chem. Rev. 111, 354–396 (2011). doi:10.1021/cr100216y.
  • Y. Mizuhata, T. Sasamori, and N. Tokitoh, Chem. Rev. 109, 3479–3511 (2009). doi:10.1021/cr900093s.
  • S. Raoufmoghaddam, Y.P. Zhou, Y. Wang, and M. Driess, J. Organomet. Chem. 829, 2–10 (2017). doi:10.1016/j.jorganchem.2016.07.014.
  • B. Blom, D. Gallego, and M. Driess, Inorg. Chem. Front. 1, 134–148 (2014). doi:10.1039/C3QI00079F.
  • S.I. Shoda, S. Iwata, K. Yajima, K. Yagi, Y. Ohnishi, and S. Kobayashi, Tetrahedron. 53, 15281–15295 (1997). doi:10.1016/S0040-4020(97)00963-0.
  • S. Kobayashi, S. Iwata, and M. Hiraishi, J. Am. Chem. Soc. 116, 6047–6048 (1994). doi:10.1021/ja00092a097.
  • W.A. Hermann, M. Denk, J. Behm, W. Scherer, F. Klingan, H. Bock, B. Solouki, and M. Wagner, Angew. Chem. Int. Ed. 31, 1485–1488 (1992). doi:10.1002/anie.199214851.
  • R.J. Baker, C. Jones, D.P. Mills, G.A. Pierce, and M. Waugh, Inorg. Chim. Acta. 361, 427–435 (2008). doi:10.1016/j.ica.2006.12.014.
  • A.V. Piskunov, I.A. Aivaz’yan, V.K. Cherkasov, and G.A. Abakumov, J. Organomet. Chem. 691, 1531–1534 (2006). doi:10.1016/j.jorganchem.2005.11.064.
  • M. Veith, Angew. Chem. Int. Ed. 14, 263–264 (1975). doi:10.1002/anie.197502631.
  • P. Park, A. Schäfer, A. Mitra, D. Haase, W. Saak, R. West, and T. Müller, J. Organomet. Chem. 695, 398–408 (2010). doi:10.1016/j.jorganchem.2009.10.034.
  • M. Denk, R. Lennon, R. Hayashi, R. West, A.V. Belyakov, H.P. Verne, A. Haaland, M. Wagner, and N. Metzler, J. Am. Chem. Soc. 116, 2691–2692 (1994). doi:10.1021/ja00085a088.
  • R.K. Raut, S.F. Amin, P. Sahoo, V. Kumar, and M. Majumdar, Inorganics. 6, 69 (2018). doi:10.3390/inorganics6030069.
  • Y.S. Chen and F. Wang, ACS Omega. 5, 30210–30225 (2020). doi:10.1021/acsomega.0c04682.
  • Y.S. Chen, L.F. Yao, and F. Wang, J. Mol. Model. 29, 52 (2023). doi:10.1007/s00894-023-05459-x.
  • M.J. Ajitha and C.H. Suresh, J. Org. Chem. 77, 1087–1094 (2012). doi:10.1021/jo202382g.
  • J. Mathew and C.H. Suresh, Inorg. Chem. 49, 4665–4669 (2010). doi:10.1021/ic1004243.
  • S. Anila, C.H. Suresh, and H.F. Schaefer III, J. Phys. Chem. A. 126, 4952–4961 (2022). doi:10.1021/acs.jpca.2c03221.
  • C.H. Suresh, G.S. Remya, and P.K. Anjalikrishna, Wiley Interdiscip. Rev. Comput. Mol. Sci. 12, e1601 (2022). doi:10.1002/wcms.1601.
  • M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, G.A. Petersson, H. Nakatsuji, X. Li, M. Caricato, A.V. Marenich, J. Bloino, B.G. Janesko, R. Gomperts, B. Mennucci, H.P. Hratchian, J.V. Ortiz, A.F. Izmaylov, J.L. Sonnenberg, F. Ding, F. Lipparini, F. Egidi, J. Goings, B. Peng, A. Petrone, T. Henderson, D. Ranasinghe, V.G. Zakrzewski, J. Gao, N. Rega, G. Zheng, W. Liang, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, K. Throssell, J.A. Montgomery Jr, J.E. Peralta, F. Ogliaro, M.J. Bearpark, J.J. Heyd, E.N. Brothers, K.N. Kudin, V.N. Staroverov, T.A. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A.P. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, J.M. Millam, M. Klene, C. Adamo, R. Cammi, J.W. Ochterski, R.L. Martin, K. Morokuma, O. Farkas, J.B. Foresman, and D.J. Fox, Gaussian 09, Revision D.01 (Gaussian, Inc., Wallingford, CT, 2013).
  • D. Feller, J. Comput. Chem. 17, 1571–1586 (1996). doi:10.1002/(SICI)1096-987X(199610)17:13<1571::AID-JCC9>3.0.CO;2-P.
  • S.F. Boys and F. Bernardi, Mol. Phys. 19, 553–566 (1970). doi:10.1080/00268977000101561.
  • R.F.W. Bader, M.T. Carroll, J.R. Cheeseman, and C. Chang, J. Am. Chem. Soc. 109, 7968–7979 (1987). doi:10.1021/ja00260a006.
  • T. Lu and F.W. Chen, J. Comput. Chem. 33, 580–592 (2012). doi:10.1002/jcc.22885.
  • R. Dennington, T. Keith, and J.S. Millam, GaussView, Version 5 (Semichem Inc., Shawnee Mission, KS, 2009).
  • A.E. Reed, L.A. Curtiss, and F. Weinhold, Chem. Rev. 88, 899–926 (1988). doi:10.1021/cr00088a005.
  • E.G. Hohenstein and C.D. Sherrill, J. Chem. Phys. 132, 184111–184120 (2010). doi:10.1063/1.3426316.
  • R.M. Parrish, L.A. Burns, D.G.A. Smith, A.C. Simmonett, A.E. DePrince III, E.G. Hohenstein, U. Bozkaya, A.Y. Sokolov, R. Di Remigio, R.M. Richard, J.F. Gonthier, A.M. James, H.R. McAlexander, A. Kumar, M. Saitow, X. Wang, B.P. Pritchard, P. Verma, H.F. Schaefer III, K. Patkowski, R.A. King, E.F. Valeev, F.A. Evangelista, J.M. Turney, T.D. Crawford, and C.D. Sherrill, J. Chem. Theory Comput. 13, 3185–3197 (2017). doi:10.1021/acs.jctc.7b00174.
  • Y.S. Chen, L.F. Yao, and F. Wang, Molecules. 28, 2577 (2023). doi:10.3390/molecules28062577.

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