Molecular structures of 3,4-dichloro-2,5-diamido-substituted pyrrole anion dimers, their deprotonation reactions in systems with and without fluoride ion

Journal of Molecular Structure: THEOCHEM

Volumn 772, Issue 1-3, 2006, Pages 23-30

  Navakhun, Korakot ^a   Ruangpornvisuti, Vithaya ^b  

^a RAMKHAMHAENG UNIVERSITY   (Thailand)

^b CHULALONGKORN UNIVERSITY   (Thailand)

Author keywords

Deprotonation; DFT; Fluoride; Molecular structure; Pyrrolic anion dimer

Indexed keywords

EID: 33748165264     PISSN: 01661280     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.theochem.2006.06.013     Document Type: Article

References (27)

1. A. Bianchi, K. Bowman-James, E. García-España (Eds.), Supramolecular Chemistry of Anions, Wiley-VCH, New York, 1997.
2. Gale P.A. Anion coordination and anion-directed assembly: highlights from 1997 and 1998. Coord. Chem. Rev. 199 (2000) 181
3. Gale P.A. Anion receptor chemistry: highlights from 1999. Coord. Chem. Rev. 213 (2001) 79
4. Beer P.D., and Gale P.A. Anion recognition and sensing: the state of the art and future perspectives. Angew. Chem. Int. Ed. 40 (2001) 486
5. Hasenknopf B., Lehn J.M., Kniesel B.O., Baum G., and Fenske D. Self-assembly of a circular double helicate. Angew. Chem. Int. Ed. Engl. 35 (1996) 1838
6. Hasenknopf B., Lehn J.M., Boumediene N., Dupont-Gervais A., van Dorsselar A., Kniesel B.O., and Fenske D. Self-assembly of tetra- and hexanuclear circular helicates. J. Am. Chem. Soc. 119 (1997) 10956
7. Sánchez-Quesadam J., Seel C., Prados P., and de Mendoza J. Anion helicates: double strand helical self-assembly of chiral bicyclic guanidinium dimers and tetramers around sulfate templates. J. Am. Chem. Soc. 118 (1996) 277
8. Wisner J.A., Beer P.D., and Drew M.G.B. A demonstration of anion templation and selectivity in pseudorotaxane formation. Angew. Chem. Int. Ed. Engl. 40 (2001) 3606
9. Keegan J., Kruger P.E., Nieuwenhuyzen M., O'Brien J., and Martin N. Anion directed assembly of a dinuclear double helicate. Chem. Commun. (2001) 2192
10. Gale P.A., Camiolo S., Chapman C.P., Light M.E., and Hursthouse M.B. Hydrogen-bonding pyrrolic amide cleft anion receptors. Tetrahedron Lett. 42 (2001) 5095
11. Gale P.A., Camiolo S., Tizzard G.J., Chapman C.P., Light M.E., Coles S.J., and Hursthouse M.B. 2-Amidopyrroles and 2,5-diamidopyrroles as simple anion binding agents. J. Org. Chem. 66 (2001) 7849
12. Dennault G., Gale P.A., Hursthouse M.B., Light M.E., and Warriner C.N. Anion complexation and electrochemical behaviour of ferrocene-appended amido-pyrrole clefts. N. J. Chem. (2002) 811
13. Camiolo S., Gale P.A., Hursthouse M.B., and Light M.E. Nitrophenyl derivatives of pyrrole 2,5-diamides: structural behaviour, anion binding and colour change signalled deprotonation. Org. Biomol. Chem. 1 (2003) 741
14. Camiolo S., Gale P.A., Hursthouse M.B., Light M.E., and Shi A.J. Solution and solid-state studies of 3,4-dichloro-2,5-diamidopyrroles: formation of an unusual anionic narcissistic dimer. Chem. Commun. (2002) 758
15. Gale P.A., Navakhun K., Camiolo S., Light M.E., and Hursthouse M.B. Anion-anion assembly: a new class of anionic supramolecular polymer containing 3,4-dichloro-2,5-diamido-substituted pyrrole anion dimers. J. Am. Chem. Soc. 124 (2002) 11228
16. Becke A.D. Density-functional thermochemistry. III. The role of exact exchange. J. Chem. Phys. 98 (1993) 5648
17. Lee C., Yang W., and Parr R.G. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys. Rev. B37 (1988) 785
18. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery, Jr., T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, J.A. Pople, Gaussian 03, Revision B.03, Gaussian, Inc., Pittsburgh PA, 2003.
19. Molden 4.2: G. Schaftenaar, CAOS/CAMM Center Nijmegen, Toernooiveld, Nijmegen, The Netherlands, 1991.
20. P. Flükiger, H.P. Lüthi, S. Portmann, J. Weber, Molekel 4.3: Swiss Center for Scientific Computing, Manno, Switzerland, 2000.
21. Sabin J.R., Trickey S.B., Apell S.P., and Oddershede J. Molecular shape, capacitance, and chemical hardness. Int. J. Quantum Chem. 77 (2000) 358
22. Koopmans T. Über die Zuordnung von Wellenfunktionen und Eigenwerten zu den Einzelnen Elektronen Eines Atoms. Physica 1 (1934) 104
23. Thipyapong K., Arano Y., and Ruangpornvisuti V. Conformational investigation of benzylhydroxamamide, its oxotechnetium(V) complexes and determination of their reaction energies. J. Mol. Struct. (Theochem) 14 (2004) 65
24. Ruangpornvisuti V., and Wanno B. A DFT investigation of conformational geometries and interconversion equilibria of phenylthiosemicarbazone and its complexation with zinc. J. Mol. Model. 10 (2004) 418
25. Wanno B., and Ruangpornvisuti V. Tautomeric and rotameric transformations of 4-methyl-3,6-pyridazinedione isomers. Chem. Phys. Lett. 415 (2005) 176
26. Boonchu T., Pulpoka B., and Ruangpornvisuti V. Protonation and energetical investigations of calix[4]-cyclen-benzo-crown-6 and its complexes with zinc and copper. Bull. Korean. Soc. 25 (2004) 819
27. Chantarasiri N., Ruangpornvisuti V., Muangsin N., Detsen H., Mananunsap T., Batiya C., and Chaichit N. Structure and physico-chemical properties of hexadentate Schiff base zinc complexes derived from salicylaldehydes and triethylenetetra. J. Mol. Struct. 701 (2004) 93