Silaphenolates and silaphenylthiolates: Two unexplored unsaturated silicon compound classes influenced by aromaticity

Molecules

Volumn 17, Issue 1, 2012, Pages 369-389

  Rouf, Alvi Muhammad ^a   Ottosson, Henrik ^a  

^a UPPSALA UNIVERSITY   (Sweden)

Author keywords

Aromaticity; Quantum chemical calculations; Silicon

Indexed keywords

HYDROXYBENZOIC ACID DERIVATIVE; ORGANOSILICON DERIVATIVE;

ARTICLE; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; COMPUTER SIMULATION; CONFORMATION; QUANTUM THEORY; THERMODYNAMICS;

COMPUTER SIMULATION; HYDROXYBENZOIC ACIDS; MODELS, CHEMICAL; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; ORGANOSILICON COMPOUNDS; QUANTUM THEORY; THERMODYNAMICS;

EID: 84856186967     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules17010369     Document Type: Article

References (35)

1. Apeloig, Y.; Karni, M. Theoretical aspects and quantum mechanical calculations of silaaromatic compounds. In The Chemistry of Organic Silicon Compounds, Rappoport, Z., Apeloig, Y., Eds.; Wiley: Chichester, UK, 1998; Volume 2, pp. 1-101.
2. Tokitoh, N. New progress in the chemistry of stable metallaaromatic compounds of heavier group 14 elements. Acc. Chem. Res. 2004, 37, 86-94.
3. Lee, V.Y.; Sekiguchi, A. Aromaticity of group 14 organometallics: Experimental aspects. Angew. Chem. Int. Ed. 2007, 46, 6596-6620. (Pubitemid 47407641)
4. Tokitoh, N.; Wakita, K.; Okazaki, R.; Nagase, S.; Schleyer, P.V.R.; Jiao, H. Stable neutral silaaromatic compound, 2-{2,4,6-Tris[bis(trimethylsilyl) methyl]phenyl}-2-silanaphthalene. J. Am. Chem. Soc. 1997, 119, 6951-6952. (Pubitemid 27343534)
5. Tokitoh, N.; Wakita, K.; Matsumoto, T.; Sasamori, T.; Okazaki, R.; Takagi, N.; Kimurac, M.; Nagase, S. The chemistry of stable silabenzenes. J. Chin. Chem. Soc. 2008, 55, 487-507.
6. Tanabe, Y.; Mizuhata, Y.; Tokitoh, N. Synthesis and structure of a heavier congener of biphenyl: 1,1'-Disila-4,4'-biphenyl. Organometallics 2010, 29, 721-723.
7. Morkin, T.L.; Leigh, W.J. Substituent effects on the reactivity of the silicon-carbon double bond. Acc. Chem. Res. 2001, 34, 129-136. (Pubitemid 32167862)
8. West, R. Multiple Bonds to Silicon: 20 Years Later. Polyhedron 2002, 21, 467-472.
9. Gusel'nikov, L. Hetero-p-systems from [2+2] cycloreversions. Part 1. Gusel'nikov-flowers route to silenes and origination of the chemistry of doubly bonded silicon. Coord. Chem. Rev. 2003, 244, 149-240.
10. Ottosson, H.; Steel, P.G. Silylenes, silenes, and disilenes: Novel silicon based reagents for organic synthesis? Chem. Eur. J. 2006, 12, 1576-1585.
11. Ottosson, H.; Eklöf, A.M. Silenes: Connectors between classical alkenes and non-classical heavy alkenes. Coord. Chem. Rev. 2008, 252, 1287-1314.
12. Fischer, R.F.; Power, P.P. p-Bonding and the lone pair effect in multiple bonds involving heavier main group elements: Developments in the new millennium. Chem. Rev. 2010, 110, 3877-3923.
13. Apeloig, Y.; Karni, M. Substituent effects on the carbon-silicon double bond of monosubstituted silenes. J. Am. Chem. Soc. 1984, 106, 6676-6682.
14. Ottosson, H. Zwitterionic silenes: Interesting goals for synthesis? Chem. Eur. J. 2003, 9, 4144-4155.
15. Apeloig, Y.; Bendikov, M.; Yuzefovich, M.; Nakash, M.; Bravo-Zhivotovskii, D.; Bläser, D.; Böse, R. Novel stable silenes via a Sila-Peterson-type reaction. Molecular structure and reactivity. J. Am. Chem. Soc. 1996, 118, 12228-12229. (Pubitemid 27006574)
16. Bendikov, M.; Quadt, S.R.; Rabin, O.; Apeloig, Y. Addition of nucleophiles to silenes. A theoretical study of the effect of substituents on their kinetic stability. Organometallics 2002, 21, 3939-3939.
17. Leigh, W.J.; Owens, T.R.; Bendikov, M.; Zade, S.S.; Apeloig, Y. A combined experimental and theoretical study of the kinetics and mechanism of the addition of alcohols to electronically stabilized silenes: A new mechanism for the addition of alcohols to the Si=C bond. J. Am. Chem. Soc. 2006, 128, 10772-10783. (Pubitemid 44277766)
18. Guliashvili, T.; Tibbelin, J.; Ryu, R.; Ottosson, H. Unsuccessful attempts to add alcohols to transient 2-amino-2-siloxysilenes-Leading to a new benign route for base-free alcohol protection. Dalton Trans. 2010, 39, 9379-9385.
19. El-Nahas, A.M.; Johansson, M.; Ottosson, H. Reverse Si=C bond polarization as a means for stabilization of silabenzenes: A computational investigation. Organometallics 2003, 22, 5556-5566.
20. Guliashvili, T.; El-Sayed, I.; Fischer, A.; Ottosson, H. The first isolable 2-silenolate. Angew. Chem. Int. Ed. 2003, 42, 1640-1642. (Pubitemid 36514380)
21. Eklöf, A.M.; Ottosson, H. Effects of substituents and counterions on the structure of silenolates: A Computational study. Tetrahedron 2009, 65, 5521-5526.
22. Bravo-Zhivotovskii, D.; Apeloig, Y.; Ovchinnikov, Y.; Igonin, V.; Struchkov, Y.T. A novel route to the trisilacyclobutane moiety. A possible silene-disilene reaction. J. Organomet. Chem. 1993, 446, 123-129.
23. Ohshita, J.; Masaoka, Y.; Masaoka, S.; Ishikawa, M.; Tachibana, A.; Yano, T.; Yamabe, T. Silicon-Carbon Unsaturated Compounds.: XLVIII. Synthesis and Reactions of Silicon Analogs of Lithium Enolates. J. Organomet. Chem. 1994, 473, 15-17.
24. 2Si=C(OLi)Ad with a doubly bonded. Angew. Chem. Int. Ed. 2010, 122, 4178-4181.
25. Zhao, Y.; Truhlar, D.G. The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: Two new functionals and systematic testing of four M06-class functionals and 12 other functionals. Theor. Chem. Acc. 2008, 120, 215-241.
26. Zhao, Y.; Truhlar, D.G. Density functionals with broad applicability in chemistry. Acc. Chem. Res. 2008, 41, 157-167.
27. Krishnan, R.; Binkley, J.S.; Seeger, R.; Pople, J. Selfconsistent molecular orbital methods. XX. A basis set for correlated wave functions. J. Chem. Phys. 1980, 72, 650-654.
28. Becke, A. Density functional thermochemistry. III. The role of exact exchange. J. Chem. Phys. 1993, 98, 5648-5652.
29. Stephens, P.J.; Devlin, F.J.; Chabalowski, C.F.; Frisch, M.J. Ab Initio calculation of vibrational absorption and circular dichroism spectra using density functional force fields. J. Phys. Chem. 1994, 98, 11623-11627.
30. Wolinski, K.; Hinton, J.F.; Pulay, P. Efficient implementation of the gauge-independent atomic orbital method for NMR chemical shift calculations. J. Am. Chem. Soc. 1990, 112, 8251-8260.
31. Frisch, M.J.; Trucks, G.W.; Schlegel, H.B.; Scuseria, G.E.; Robb, M.A.; Cheeseman, J.R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G.A.; et al. Gaussian 09, Revision A.02; Gaussian, Inc.: Wallingford, CT, USA, 2009.
32. Schleyer, P.V.R.; Maerker, C.; Dransfeld, A.; Jiao, H.; von Eikema Hommes, N.J.R. Nucleus- Independent Chemical Shifts (NICS): A simple and efficient aromaticity Probe. J. Am. Chem. Soc. 1996, 118, 6317-6318. (Pubitemid 26236878)
33. Chen, Z.; Wannere, C.S.; Corminboeuf, C.; Puchta, R.; Schleyer, P.V.R. Nucleus-Independent Chemical Shifts (NICS) as an aromaticity criterion. Chem. Rev. 2005, 105, 3842-3888. (Pubitemid 41630338)
34. Fallah-Bagher-Shaidaei, H.; Wannere, C.S.; Corminboeuf, C.; Puchta, R.; Schleyer, P.V.R. Which NICS aromaticity index for planar p rings is best? Org. Lett. 2006, 8, 863-866. (Pubitemid 43411984)
35. Allen, F.H.; Kennard, O.; Watson, D.G.; Brammer, L.; Orpen, A.G.; Taylor, R. Tables of bond lengths determined by X-ray and neutron diffraction. Part I. Bond lengths in organic compounds. J. Chem. Soc. Perkin Trans. II 1987, S1-S19.