Supporting Information. DFT calculations of pentalenoquinones: towards the interception of 2-bromopentalene-1,5-dione
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1 Supporting Information DFT calculations of pentalenoquinones: towards the interception of 2-bromopentalene-1,5-dione Taner Atalar, a Fatih Algı, a,b and Metin Balci a * a Department of Chemistry, Middle East Technical University, 06531, Ankara, Turkey b Laboratory of Organic Materials, Department of Chemistry, Çanakkale Onsekiz Mart University, 17100, Çanakkale, Turkey mbalci@metu.edu.tr This paper is dedicated to Professor Udo H. Brinker on the occasion of his 65 th birthday General Geometry optimizations were performed at the level of B3LYP/6-311+G(d,p) 1-3. The nucleus independent chemical shift (NICS) 4 was used as a descriptor of aromaticity from the magnetic point of view. The index is defined as the negative value of the absolute magnetic shielding computed at ring centers 5 or another interesting point of the system. 6 In this study, NICS values were computed with GIAO 7 B3LYP/6-311G (d,p) // B3LYP/6-311+G(d,p). NICS (0) was calculated at the geometrical center of the ring. For each set of calculations, vibrational analyses were done (using the same basis set employed in the corresponding geometry optimizations). The normal mode analysis for each structure yielded no imaginary frequencies for the 3N 6 vibrational degrees of freedom, where N is the number of atoms in the system. This indicates that the structure of each molecule corresponds to at least a local minimum on the potential energy surface. All the calculations for the geometry optimizations and energies were performed using Gaussian 98 program package 7 and Spartan 06 package 8 programme. ISSN Page S1 ARKAT USA, Inc.
2 Cartesian Coordinates Cartesian Coordinates (Angstroms) Atom X Y Z C C C C C C C C C C C C C C C C O O O O H H H H H H H H Point Group = CS ISSN Page S2 ARKAT USA, Inc.
3 Cartesian Coordinates (Angstroms) Atom X Y Z C C C C C C C C C C C C C C C C O O O O H H H H H H H H Point Group = CS ISSN Page S3 ARKAT USA, Inc.
4 Cartesian Coordinates (Angstroms) Atom X Y Z C C C C C C C C C C C C C C C C O O O O H H H H H H H H Point Group = C2V ISSN Page S4 ARKAT USA, Inc.
5 Cartesian Coordinates (Angstroms) Atom X Y Z C C C C C C C C C C C C C C C C O O O O H H H H H H H H Point Group = C2H ISSN Page S5 ARKAT USA, Inc.
6 Cartesian Coordinates (Angstroms) Atom X Y Z C C C C C C C C C C C C C C C C H H H H H H H H H H H H Point Group = C2H ISSN Page S6 ARKAT USA, Inc.
7 Cartesian Coordinates (Angstroms) Atom X Y Z C C C C C C C C C C C C C C C C O O O O H H H H H H Br Br Point Group = CS ISSN Page S7 ARKAT USA, Inc.
8 Cartesian Coordinates (Angstroms) Atom X Y Z C C C C C C C C C C C C C C C C O O O O H H H H H H Br Br Point Group = CS ISSN Page S8 ARKAT USA, Inc.
9 Cartesian Coordinates (Angstroms) Atom X Y Z C C C C C C C C C C C C C C C C O O O O H H H H H H Br Br Point Group = CS ISSN Page S9 ARKAT USA, Inc.
10 Cartesian Coordinates (Angstroms) Atom X Y Z C C C C C C C C C C C C C C C C O O O O H H H H H H Br Br Point Group = CS ISSN Page S10 ARKAT USA, Inc.
11 Cartesian Coordinates (Angstroms) Atom X Y Z C C C C C C C C C C C C C C C C H H H H H H H H H H Br Br Point Group = CS ISSN Page S11 ARKAT USA, Inc.
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22 References 1. Becke, A. D. J. Chem. Phys., 1993, 98, Becke, A. D. Phys. Rev. A, 1998, 38, Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B, 1988, 37, Schleyer, P. R.; Maerker, C.; Dransfeld, A.; Jiao, H.; Hommes, N. J. R. E. J. Am. Chem. Soc., 1996, 118, Schleyer, P. R.; Monohar, M.; Wang, Z.; Kiran, B.; Jiao, H.; Puchta, R.; Hommes, N. J. R. Org. Lett., 2001, 3, Krygowski, T. M.; Ejsmont, K.; Stepien, B. T.; Cyran ski, M. K.; Poater, J.; Sola, M. J. Org. Chem., 2004, 69, Wolinski, K.; Hilton, J. F.; Pulay, P. J. Am. Chem. Soc., 1990, 112, M.F. Frisch, M. F.; Trucks, G. W.; Schleged, H. B.; Scuseria, G. E.; Robb, M. A.; Cheesman, J. R. et al., Gaussian 98, Revision A.6, Gaussian Inc., Pitsburg, PA, SPARTAN 06, Wavefunction Inc., Irvine CA,USA. ISSN Page S22 ARKAT USA, Inc.