A DFT INVESTIGATION OF A POLYCYCLIC STANNYLENE MODEL; STRUCTURAL CHARACTERIZATION AND STABILITY ASSESSMENT

Ionuț-Tudor  MORARU; Gabriela  NEMEȘ

doi:10.24193/subbchem.2019.2.37

Authors

Ionuț-Tudor MORARU Department of Chemistry and Chemical Engineering, Babeş-Bolyai University, Cluj-Napoca, Romania. Email: mit@chem.ubbcluj.ro. https://orcid.org/0000-0002-3041-8032
Gabriela NEMEȘ Department of Chemistry and Chemical Engineering, Babeş-Bolyai University, Cluj-Napoca, Romania. Email: gabriela.nemes@ubbcluj.ro.

DOI:

https://doi.org/10.24193/subbchem.2019.2.37

Keywords:

stannylene, stilbene, DFT calculations, NBO analyses

Abstract

The first part of this study aims at evaluating by DFT methods the structural features and the stability of a stannylene derivative, Sn(II) being included into an extended polycyclic framework. Natural Bond Orbital (NBO) analyses are performed in order to understand bonding patterns and also the role of secondary electronic effects on the stability of this unsaturated derivative. In the second part, the coordination of NHC and THF ligands to the Sn(II) atom of the polycyclic stannylene species are investigated. The strength of these interactions and the nature of the chemical bonds formed are also discussed.

References

W. P. Neumann, Chem. Rev., 1991, 91, 311-334.

J. Barrau; G. Rima, Coord. Chem. Rev., 1998, 178-180, 593-622.

Y. Mizuhata; T. Sasamori; N. Tokitoh, Chem. Rev., 2009, 109, 3479-3511.

F. Lollmahomed; L. A. Huck; C. A. Harrington; S. S. Chitnis; W. J. Leigh, Organometallics, 2009, 28, 1484-1494.

P. A. Rupar; V. N. Staroverov; K. M. Baines, Science, 2008, 322, 1360-1363.

S. Nagendran; H. W. Roesky, Organometallics, 2008, 27, 457-492.

S. K. Mandal; H. W. Roesky, Chem. Commun., 2010, 6016-6041.

M. Asay; C. Jones; M. Driess, Chem. Rev., 2011, 111, 354-396.

G. J. Trinquier, Am. Chem. Soc., 1990, 112, 2130-2131.

P. P. Power, Chem. Rev., 1999, 99, 3463-3504.

J. Barrau; J. Escudié; J. Satgé, Chem. Rev., 1990, 90, 283-319.

J. T. B. H. Jastrzebski; P. A. Van der Schaaf; J. Boersma; G. Van Koten; M. C. Zoutberg; D. Heijdenrijk, Organometallics, 1989, 8, 1373-1375.

M. P. Bigwood; P. J. Corvan; J. J. Zuckerman, J. Am. Chem. Soc., 1981, 103, 7643-7646.

C. Bibal; S. Mazières; H. Gornitzka; C. Couret, Angew. Chem. Int. Ed., 2001, 40, 952-954.

S.-P. Chia; H.-X. Yeong; C.-W. So, Inorg. Chem., 2012, 51, 1002-1010.

S. Khan; P. P. Samuel; R. Michel; J. M. Dieterich; R. A. Mata; J.-P. Demers; A. Lange; H. W. Roesky; D. Stalke, Chem. Commun., 2012, 48, 4890-4892.

B. Kašná; R. Jambor; M. Schürman; K. Jurkschat, J. Organomet. Chem., 2008, 693, 3446-3450.

M. El Ezzi; R. Lenk; D. Madec; J.-M. Sotiropoulos; S. Mallet-Ladeira; A. Castel, Angew. Chem. Int. Ed., 2015, 127, 819-822.

N. Deak; P. M. Petrar; S. Mallet-Ladeira; L. Silaghi-Dumitrescu; G. Nemeş; D. Madec, Chem. - Eur. J., 2016, 22, 1349-1354.

N. Deak; O. Thillaye du Boullay; I.-T. Moraru; S. Mallet-Ladeira; D. Madec; G. Nemes, Dalton Trans., 2019, 48, 2399-2406.

N. Deak; I.-T. Moraru; N. Saffon-Merceron; D. Madec; G. Nemes, Eur. J. Inorg. Chem., 2017, 36, 4214-4220.

A. J. Arduengo; R. L. Harlow; M. Kline, J. Am. Chem. Soc., 1991, 113, 361-363.

D. Nemcsok; K. Wichmann; G. Frenking, Organometallics, 2004, 23, 3640-3646.

F. E. Hahn; L.Wittenbecher; R. Boese; D. Bläser, Chem. Eur. J. 1999, 5, 1931-1935.

R. W. Alder; P. R. Allen; M. Murray; A. G. Orpen, Angew. Chem. Int. Ed. Engl., 1996, 35, 1121-1122.

A. J. Arduengo; R. H. V. Dias; J. C. Calabrese; F. Davidson, Inorg. Chem., 1993, 32, 1541-1542.

A. Sidiropoulos; C. Jones; A. Stasch; S. Klein; G. Frenking, Angew. Chem. Int. Ed., 2009, 48, 9701-9704.

P. A. Rupar; V. N. Staroverov; K. M. Baines, Organometallics, 2010, 29, 4871-4881.

A. C. Filippou; O. Chernov; B. Blom; K. W. Stumpf; G. Schnakenburg, Chem. Eur. J., 2010, 16, 2866-2872.

R. S. Ghadwal; H. W. Roesky; S. Merkel; J. Henn; D. Stalke, Angew. Chem. Int. Ed., 2009, 48, 5683-5686.

A. C. Filippou; O. Chernov; G. Schnakenburg, Chem. Eur. J., 2011, 17, 13574-13583.

H. Cui; C. Cui, Dalton Trans., 2011, 40, 11937-11940.

K. C. Thimer; I. S. M. Al-Rafia; M. J. Ferguson; R. McDonald; E. Rivard, Chem. Commun., 2009, 7119-7121.

B. Bantu; G. M. Pawar; U. Decker; K. Wurst; A. M. Schmidt; M. R. Buchmeiser, Chem. Eur. J., 2009, 15, 3103-3109.

D. Matioszek; T.-G. Kocsor; A. Castel; G. Nemes; J. Escudié; N. Saffon, Chem. Commun., 2012, 48, 3629-3631.

T.-G. Kocsor; G. Nemes; N.Saffon; S. Mallet-Ladeira; D. Mandec; A. Castel; J. Escudié, Dalton Trans., 2014, 43, 2718-2721.

P. M. Petrar; R. Septelean; H. Gornitska; G. Nemes, J. Organomet. Chem., 2015, 787, 14-18.

R. Septelean; G. Nemes; J. Escudié; I. Silaghi-Dumitrescu; H. Ranaivonjatovo; P. M. Petrar; H. Gornitzka; L. Silaghi-Dumitrescu; N. Saffon, Eur. J. Inorg. Chem., 2009, 628-634.

R. Septelean; H. Ranaivonjatovo; G. Nemes; J. Escudié; I. Silaghi-Dumitrescu; H. Gornitzka; L. Silaghi-Dumitrescu; S. Massou, Eur. J. Inorg. Chem., 2006, 4237-4241.

G. Cretiu Nemes; H. Ranaivonjatovo; J. Escudié; I. Silaghi-Dumitrescu; L. Silaghi-Dumitrescu; H. Gornitzka; Eur. J. Inorg. Chem., 2005, 1109-1113.

T.-G. Kocsor; D. Matioszek; G. Nemes; A. Castel; J. Escudié; P. Petrar; N. Saffon-Merceron; I. Haiduc, Inorg. Chem., 2012, 51, 7782−7787.

T.-G. Kocsor; P. Petrar; G. Nemeş; A. Castel; J. Escudié; N. Deak; L. Silaghi-Dumitrescu; Comput. Theor. Chem., 2011, 974, 117-121.

R. Septelean, I.-T. Moraru; T. Kocsor; N. Deak; N. Saffon; A. Castel; G. Nemes, Inorg. Chim. Acta, 2018, 475, 112-119.

L. Buta; R. Septelean; I.-T. Moraru; A. Soran; L. Silaghi-Dumitrescu; G. Nemes, Inorg. Chim. Acta, 2019, 486, 648-653.

P. M. Petrar; R. Septelean; H. Gornitska; G. Nemes, J. Organomet. Chem., 2015, 787, 14-18.

G. Cretiu Nemes; L. Silaghi-Dumitrescu; I. Silaghi-Dumitrescu; J. Escudié; H. Ranaivonjatovo; K. C. Molloy; M. F. Mahon; J. Zukerman-Schpector, Organometallics, 2005, 24, 1134-1144.

R. Hoffmann; P. v. R. Schleyer; H. F. Schaefer, Angew. Chem. Int. Ed., 2008, 47, 7164 –7167.

I.-T. Moraru; P. M. Petrar; G. Nemes, J. Phys. Chem. A, 2017, 121, 2515-2522.

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. Marenich, J. Bloino, B. G. Janesko, R. Gomperts, B. Mennucci, H. P. Hratchian, J. V. Ortiz, A. F. Izmaylov, J. L. Sonnenberg, D. Williams-Young, 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. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, T. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. 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, D. J. Fox, Gaussian 09, revision E.01; Gaussian, Inc.: Wallingford, CT, 2009.

a) C. Lee, W. Yang, R. G. Parr. Phys. Rev. B: Condens. Matter Mater. Phys. 1988, 37, 785. b) A. D. Becke. J. Chem. Phys. 1993, 98, 5648-5652.

S. Grimme, J. Antony, S. Ehrlich, H. Krieg. J. Chem. Phys. 2010, 132, 154104.

a) A. Schafer, C. Huber, R. Ahlrichs, J. Chem. Phys. 1994, 100, 5829; b) D. Rappoport, F. Furche. J. Chem. Phys. 2010, 133, 134105.

a) F. Weinhold, C. R. Landis, Valency and Bonding: A Natural Bond Orbital Donor-Acceptor Perspective; Cambridge Univ. Press: Cambridge, U.K., 2005. b) F. Weinhold, C. R. Landis, Discovering Chemistry with Natural Bond Orbitals; Wiley-Interscience: Hoboken, NJ., 2012. c) F. Weinhold, C. R. Landis, E. G. Glendening, Int. Rev. Phys. Chem. 2016, 35, 399