Structural and Molecular Orbital Studies of Si-Phenyl Silaanthracenes

REFERENCES

• Reikhsfel'd , V. O. 1985 . “ Phenheterasilanes and their analogs ” . In Advances in organosilicon chemistry , Edited by: Voronkov , M. G. Moscow : Mir Pub .
   Google Scholar
• Raabe , G. and Michl , J. 1985 . Multiple bonding to silicon . Chem. Rev. , 85 : 419 – 509 .
   Web of Science ®Google Scholar
• Brook , A. G. and Brook , M. A. 1996 . The chemistry of silenes . Adv. Organomet. Chem. , 39 : 71 – 158 .
   Google Scholar
• Tokitoh , N. , Wakita , K. , Okazaki , R. , Nagase , S. , Schleyer , P. v.R. and Jiao , H. A. 1997 . A stable neutral silaaromatic compound, 2-{2,4,6-Tris[bis(trimethylsilyl)methyl] phenyl}-2-silanaphthalene . J. Am. Chem. Soc. , 119 : 6951 – 6952 .
   Google Scholar
• Wakita , K. , Tokitoh , N. and Okazaki , R. 2000 . Separation of orientational disorder in the X-ray analysis of the kinetically stabilized 2-silanaphthalene . Bull. Chem. Soc. Jpn. , 73 : 2157 – 2158 .
   Google Scholar
• Wakita , K. , Tokitoh , N. , Okazaki , R. and Nagase , S. 2000 . Synthesis and properties of an overcrowded silabenzene stable at ambient temperature . Angew. Chem., Int. Ed. , 39 : 634 – 636 .
   PubMedGoogle Scholar
• Wakita , K. , Tokitoh Okazaki , R. , Takagi , N. and Nagase , S. 2000 . Crystal structure of a stable silabenzene and its photochemical valence isomerization into the corresponding silabenzvalene . J. Am. Chem. Soc. , 122 : 5648 – 5649 .
   Web of Science ®Google Scholar
• Winkel , Y. v.d. , Baar , B. L. M.v. , Bickelhaupt , F. , Kulik , W. , Sierakowski , C. and Maier , G. 1991 . Neutralization-reorganization mass spectrometry and matrix isolation of some 9-silaanthracenes . Chem. Ber. , 124 : 185 – 90 .
   Google Scholar
• Raabe , G. and Michl , J. 1989 . “ Multiple bonding to silicon ” . In The chemistry of organosilicon compounds , Edited by: Patai , S. and Rappoport , Z. 1102 – 1108 . New York : Wiley .
   Google Scholar
• Nishiyama , K. , Oba , M. , Takagi , H. , Fujii , I. , Hirayama , N. , Horiuchi , N. H. , Okutsu , T. and Hiratsuka , H. 2000 . Synthesis, structure, and photochemical reaction of 9,10-dihydro-9-silaanthracene derivatives carrying bulky substituents . J. Organomet. Chem. , 604 : 20 – 26 .
   Google Scholar
• Takeda , N. , Shinohara , A. and Tokitoh , N. 2002 . The first stable 9-silaanthracene . Organometallics , 21 : 256 – 258 .
   Google Scholar
• Hiratsuka , H. , Tanaka , M. , Okutsu , T. , Oba , M. and Nishiyama , K. 1995 . Photochemical formation of 9-silaanthracenes in rigid glass . J. Chem. Soc., Chem. Commun. , : 215 – 216 .
   Google Scholar
• Hiratsuka , H. , Tanaka , M. , Horiuchi , H. , Yoshinaga , T. , Oba , M. and Nishiyama , K. 2000 . Photophysical and photochemical processes of 9,10-dihydro-9-silaanthracenes: photochemical generation and electronic structure of 9-phenyl-9-silaanthracene . J. Organometallic Chem. , 611 : 71 – 77 .
   Google Scholar
• Stewart , J. J. P. 1989 . Optimization of parameters for semi empirical methods I . J. Comput. Chem. , 10 : 209 – 220 .
   Web of Science ®Google Scholar
• Stewart , J. J. P. 1989 . Optimization of parameters for semi empirical methods II . J. Comput. Chem. , 10 : 221 – 264 .
   Web of Science ®Google Scholar
• Leach , A. R. 1997 . Molecular modeling. , Essex : Longman .
   Google Scholar
• Fletcher , P. 1990 . Practical methods of optimization. , New York : Wiley .
   Google Scholar
• Kohn , W. and Sham , L. 1965 . Self-consistent equations including exchange and correlation effects . J. Phys. Rev. , 140 : A1133 – 1138 .
   Google Scholar
• Parr , R. G. and Yang , W. 1989 . Density functional theory of atoms and molecules , London : Oxford University Press, London .
   Google Scholar
• Becke , A. D. 1988 . Density-functional exchange-energy approximation with correct asymptotic behavior . Phys. Rev. A , 38 : 3098 – 3100 .
   PubMed Web of Science ®Google Scholar
• Vosko , S. H. , Vilk , L. and Nusair , M. 1980 . Accurate spin-dependent electron liquid. Correlation energies for local spin density calculations: a critical analysis . Can. J. Phys , 58 : 1200 – 1211 .
   Web of Science ®Google Scholar
• Lee , C. , Yang , W. and Parr , R. G. 1988 . Development of the Colle–Salvetti correlation energy formula into a functional of the electron density . Phys. Rev. B , 37 : 785 – 789 .
   PubMed Web of Science ®Google Scholar
• Spartan 06 program , Irvine, CA 92612 USA : Wavefunction Inc. .
   Google Scholar
• McKee , M. L. 2002 . Application of theoretical methods to NMR chemical shifts and coupling constants , ACS Symposium Series, No. 827 Edited by: Eaton , G. R. , Wiley , D. C. and Jardetzky , O. 135 – 149 . Washington, D. C. : American Chemical Society .
   Google Scholar
• Pulay , P. , Hinton , J. F. , Wolinski , K. and Tossel , J. A. , eds. 1993 . Nuclear magnetic shieldings and molecular structure , NATO ASI Series C Netherlands : Kluwer .
   Google Scholar
• Frisch , M. J. , Trucks , G. W. , Schlegel , H. B. , Scuseria , G. E. , Robb , M. A. , Cheeseman , J. R. , Montgomery , J. A. Jr. , Vreven , T. , Kudin , K. N. , Burant , J. C. , Millam , J. M. , Iyengar , S. S. , Tomasi , J. , Barone , V. , Mennucci , B. , Cossi , M. , Scalmani , G. , Rega , N. , Petersson , G. A. , Nakatsuji , H. , Hada , M. , Ehara , M. , Toyota , K. , Fukuda , R. , Hasegawa , J. , Ishida , M. , Nakajima , T. , Honda , Y. , Kitao , O. , Nakai , H. , Klene , M. , Li , X. , Knox , J. E. , Hratchian , H. P. , Cross , J. B. , Adamo , C. , Jaramillo , J. , Gomperts , R. , Stratmann , R. E. , Yazyev , O. , Austin , A. J. , Cammi , R. , Pomelli , C. , Ochterski , J. W. , Ayala , P. Y. , Morokuma , K. , Voth , G. A. , Salvador , P. , Dannenberg , J. J. , Zakrzewski , V. G. , Dapprich , S. , Daniels , A. D. , Strain , M. C. , Farkas , O. , Malick , D. K. , Rabuck , A. D. , Raghavachari , K. , Foresman , J. B. , Ortiz , J. V. , Cui , Q. , Baboul , A. G. , Clifford , S. , Cioslowski , J. , Stefanov , B. B. , Liu , G. , Liashenko , A. , Piskorz , P. , Komaromi , I. , Martin , R. L. , Fox , D. J. , Keith , T. , Al-Laham , M. A. , Peng , C. Y. , Nanayakkara , A. , Challacombe , M. , Gill , P. M. W. , Johnson , B. , Chen , W. , Wong , M. W. , Gonzalez , C. and Pople , J. A. 2004 . Gaussian 03, Revision C. 02 , Wallingford, CT : Gaussian, Inc. .
   Google Scholar
• Schleyer , P. R. , Kiran , B. , Simion , D. V. and Sorensen , T. S. 2000 . Does Cr(CO)3 complexation reduce the aromaticity of benzene? . J Am Chem Soc , 122 : 510 – 513 .
   Web of Science ®Google Scholar
• Dhevi , D. M. , Priyakumar , U. D. and Sastry , G. N. 2003 . Silaaromaticity in polycyclic systems: A computational study . J. Org. Chem. , 68 : 1168 – 1171 .
   PubMedGoogle Scholar
• Türker , L. , Gümü , S. and Atalar , T. 2009 . Structural and molecular orbital properties of some boroxine derivatives—A theoretical study . Bull. Korean Chem. Soc. , 30 : 2233 – 2239 .
   Google Scholar
• Beletskaya , I. P. and Zemlyansky , N. N. 1984 . “ Carbon-group IVA element compounds with a multiple pπ-pπbond: New approaches into synthesis ” . In Advances in organometalic chemistry , Edited by: Reutov , O. A. Moscow : Mir Pub .
   Google Scholar
• Ahlrichs , R. and Heinzmann , R. 1977 . Stable carbocations. CXLVI. 1,2-Diphenyl-2-norbornyl cation. Comparison of sigma and pi delocalization in phenylnorbornyl and related cations . J. Am.Chem.Soc. , 96 : 195 – 199 .
   Google Scholar
• Henamura , M. , Nagase , S. and Morokuma , K. 1981 . The stability and nature of a Si-C double bond. An ab initio MO study for 1,1-dimethylsilaethylene . Terahedron Lett. , 22 : 1813 – 16 .
   Google Scholar
• Reutov , O. A. 1984 . Advances in organometallic chemistry. , Moscow : Mir Pub .
   Google Scholar
• Pearson , R. G. 1997 . Chemical hardness , New York : Wiley-VCH .
   Google Scholar
• Hoffmann , M. R. , Yoshioka , Y. and Schaefer , H. F. III . 1983 . Vibrational frequencies for silaacetylene and its silylidene and vinylidene isomers . J. Am. Chem. Soc. , 105 : 1084 – 1088 .
   Google Scholar