Causes of nonplanarity in fluorinated 1, 3λ4δ2,2,4-benzodithiadiazines: Gas-phase electron diffraction, Ab initio and DFT structures

European Journal of Inorganic Chemistry

Volumn , Issue 3, 2005, Pages 572-581

  Turner, Andrew R ^a   Blockhuys, Frank ^b   Van Alsenoy, Christian ^b   Robertson, Heather E ^a   Hinchley, Sarah L ^a   Zibarev, Andrey V ^c   Makarov, Alexander Yu ^c   Rankin, David W H ^a  

^a UNIVERSITY OF EDINBURGH   (United Kingdom)

^b UNIVERSITY OF ANTWERP   (Belgium)

^c N N VOROZHTSOV NOVOSIBIRSK INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

Author keywords

Ab initio calculations; Antiaromaticity; Density functional calculations; Fluorinated 1,3 4 2,2,4 benzodithiadiazines; Molecular structure

Indexed keywords

ELECTRON DIFFRACTION; ELECTRONS; GASES; MOLECULAR STRUCTURE; ORGANIC COMPOUNDS; QUANTUM CHEMISTRY;

AB INITIO AND DFT; AB INITIO CALCULATIONS; ANTIAROMATICITY; DENSITY-FUNCTIONAL CALCULATIONS; FLUORINATED 1,3Λ4Δ2,2,4- BENZODITHIADIAZINE; FOLDINGS; GAS PHASE ELECTRON DIFFRACTIONS; GAS-PHASES; PLANARITY; STRUCTURAL PARAMETER;

DENSITY FUNCTIONAL THEORY;

5,6,7 TRIFLUORO 1,3LAMBDA 4 DELTA 2,2,4 BENZODITHIADIAZINE; 6,8 DIFLUORO 1,3LAMBDA 4 DELTA 2,2,4 BENZODITHIADIAZINE; BENZODITHIADIAZINE DERIVATIVE; FLUORINE DERIVATIVE; HETEROCYCLIC COMPOUND; THIADIAZINE DERIVATIVE; UNCLASSIFIED DRUG;

AB INITIO CALCULATION; ARTICLE; CHEMICAL STRUCTURE; CONFORMATION; DENSITY FUNCTIONAL THEORY; ELECTRON DIFFRACTION; FLUORINATION; GAS; INFRARED SPECTROSCOPY; QUANTUM CHEMISTRY; SOLID STATE; STRUCTURE ANALYSIS; X RAY DIFFRACTION;

EID: 14544281492     PISSN: 14341948     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejic.200400601     Document Type: Article

References (30)

1. A. V. Zibarev, Y. V. Gatilov, A. O. Miller, Polyhedron 1992, 11, 1137.
2. A. W. Cordes, M. Hojo, H. Koenig, M. C. Noble, R. T. Oakley, W. T. Pennington, Inorg. Chem. 1986, 25, 1137.
3. F. Blockhuys, S. L. Hinchley, A. Yu. Makarov, Y. V. Gatilov, A. V. Zibarev, J. D. Woollins, D. W. H. Rankin, Chem. Eur. J. 2001, 7, 3592.
4. A. Yu. Makarov, I. Yu. Bagryanskaya, F. Blockhuys, C. Van Alsenoy, Y. V. Gatilov, V. V. Knyazev, A. M. Maksimov, T. V. Mikhalina, V. E. Platonov, M. M. Shakirov, A. V. Zibarev, Eur. J. Inorg. Chem. 2003, 77.
5. P. V. Schastnev, L. N. Schegoleva, Molecular Distortion in Ionic and Excited States, CRC, Boca Raton, 1995.
6. C. M. Huntley, G. S. Laurenson, D. W. H. Rankin, J. Chem. Soc., Dalton Trans. 1980, 954.
7. Y. Murata, Y. Morino, Acta Crystallogr. 1966, 20, 605.
8. S. L. Hinchley, H. E. Robertson, K. B. Borisenko, A. R. Turner, B. F. Johnston, D. W. H. Rankin, M. Ahmadian, J. N. Jones, A. H. Cowley, Dalton Trans., in press.
9. A. W Ross, M. Fink, R. Hilderbrandt, in International Tables for Crystallography (Ed.: A. J. C. Wilson) Kluwer, Dordrecht. 1992, vol. C, p. 245.
10. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. G. Johnson, W. Chen, M. W. Wong, J. L. Andres, M. Head-Gordon, E. S. Replogle, J. A. Pople, Gaussian98, revision A.7, Gaussian Inc., Pittsburgh PA, 1998.
11. [11a] N. W. Mitzel, D. W. H. Rankin, Dalton Trans. 2003, 19, 3650.
12. [11b] N. W. Mitzel, B. A. Smart, A. J. Blake, H. E. Robertson, D. W. H. Rankin, J. Phys. Chem. 1996, 700, 9339.
13. [11c] A. J. Blake, P. T. Brain, H. McNab, J. Millar, C. A. Morrison, S. Parsons. D. W. H. Rankin, H. E. Robertson, B. A. Smart, J. Phys. Chem. 1996, 100, 12280.
14. [12a] C. Møller, M. S. Plesset, Phys. Rev. 1934, 46, 618.
15. [12b] M. Head-Gordon, J. A. Pople, M, J. Frisch. Chem. Phys. Lett. 1988, 153, 503.
16. [12c] M. J. Frisch, M. Head-Gordon, J. A. Pople, Chem. Phys. Lett. 1990, 166, 275.
17. [12d] M. J. Frisch, M. Head-Gordon, J. A. Pople, Chem. Phys. Lett. 1990, 166, 281.
18. [12e] M. Head-Gordon, T. Head-Gordon, Chem. Phys. Lett. 1994, 220, 122.
19. [12f] S. Saebo, J. Almlöf, Chem. Phys. Lett. 1989, 154, 83.
20. [13a] A. D. Becke, J. Chem. Phys. 1993, 98, 5648; C. Lee, W. Yang, R. G. Parr, Phys. Rev. B. 1988, 37, 785.
21. [13a] A. D. Becke, J. Chem. Phys. 1993, 98, 5648; C. Lee, W. Yang, R. G. Parr, Phys. Rev. B. 1988, 37, 785.
22. [13b] B. Miehlich, A. Savin, H. Still, H. Preuss, Chem. Phys. Lett. 1989, 157, 200.
23. [14a] A. D. McLean, G. S. Chandler, J. Chem. Phys. 1980, 72, 5639.
24. [14b] R. Krishnan, J. S. Binkley, R. Seeger, J. A. Pople, J. Chem. Phys. 1980, 72, 650.
25. [14c] T. Clark, J. Chandrasekhar, G. W. Spitznagel, P. v. R. Schleyer, J. Comp. Chem. 1983, 4, 294.
26. V. A. Sipachev, J. Mol. Struct. 1985, 121, 143; V. A. Sipachev, in Advances in Molecular Structure Research (Eds.: I. Hargittai, M. Hargittai), JAI, Greenwich, 1999, vol. 5, p. 263.
27. V. A. Sipachev, J. Mol. Struct. 1985, 121, 143; V. A. Sipachev, in Advances in Molecular Structure Research (Eds.: I. Hargittai, M. Hargittai), JAI, Greenwich, 1999, vol. 5, p. 263.
28. R. A. Kendall, T. H. Dunning Jr., R. J. Harrison, J. Chem. Phys. 1992, 96, 6796.
29. W. C. Hamilton, Acta Crystallogr. 1965, 18, 502.
30. S. L. Hinchley, P. Trickey, H. E. Robertson, B. A. Smart, D. W. H. Rankin, D. Leusser, B. Walfort, D. Stalke, M. Bühl, S. J. Obrey, Dalton Trans. 2002, 4607.