Synthesis, Characterization and Crystallographic Studies of Three 2-Aryl-3-methyl-4-aryl-1,3-thiazolium-5-thiolates

Petronio Filgueiras de Athayde-Filho; Joseph Miller; Alfredo Mayall Simas; Bruno Freitas Lira; José Alixandre de Souza Luis; Júlio Zuckerman-Schpector

doi:10.1055/s-2003-38070

PAPER

Synthesis, Characterization and Crystallographic Studies of Three 2-Aryl-3-methyl-4-aryl-1,3-thiazolium-5-thiolates

Petronio Filgueiras de Athayde-Filho*^a,b,c, Joseph Miller*^b,c, Alfredo Mayall Simas^c, Bruno Freitas Lira^b,c, José Alixandre de Souza Luis^b, Júlio Zuckerman-Schpector^d
^a Universidade Federal da Paraíba, Departamento de Ciências Básicas Sociais - Bananeiras - PB and Departamento de Química, João Pessoa - PB, 58051-970, Brasil
e-Mail: athayde-filho@uol.com.br;
^b Universidade Federal da Paraíba, Laboratório de Tecnologia Farmacêutica
e-Mail: millerjo@ltf.ufpb.br;
^c Universidade Federal de Pernambuco, Departamento de Química Fundamental, Recife - PE, 50670-901, Brasil
e-Mail: ams@npd.ufpe.br;
^d Universidade Federal de São Carlos, Laboratório de Estereodinâmica e Modelagem Molecular, São Carlos - SP, 13565-905, Brasil
e-Mail: julio@power.ufscar.br;

Abstract

Alle Artikel dieser Rubrik

Abstract

Mesoionic 2,4-diphenyl-3-methyl-1,3-thiazolium-5-thiolate, 2-(4′-chlorophenyl)-3-methyl-4-phenyl-1,3-thiazolium-5-thiolate and 2-(4′-chlorophenyl)-3-methyl-4-(4′-isopropyl-phenyl)-1,3-thiazolium-5-thiolate were synthesized via N-methyl-C-aryl-glycines, involving a one-pot 1,3-dipolar cycloaddition/cycloreversion sequence. The two latter mesoionic compounds are new, as are some of the intermediates. Compounds were fully characterized, while X-ray diffraction studies of the three mesoionic compounds also confirmed their structures and our definition of mesoionic compounds. In particular they showed that the mesoionic ring system has two regions in which there is electron and charge delocalization separated by what are essentially single bonds. The data also suggested a tendency for the 2- and 4-aryl groups to lie in the plane of the mesoionic ring.

Key words

mesoionic - betaine - 1,3-thiazolium-5-thiolates - synthesis - crystallography

Volltext

Referenzen

References

1 Cheung KK. Galembeck SE. Miller J. Oliveira MB. Pereira AB. Simas AM. Acta Cryst., Sect. C 1991, 47: 2630

2 Simas AM. Miller J. Maciel MAM. 16a Reunião Anual da SBQ - Caxambu - MG Resumo QT - 01 1993,

3 Oliveira MB. Miller J. Pereira AB. Galembeck SE. Moura GLC. Simas AM. Phosphorus, Sulfur Silicon Relat. Elem. 1996, 108: 75

4 Athayde-Filho PF. Miller J. Simas AM. Can. J. Chem. 1998, 76: 864

5 Athayde-Filho PF. Miller J. Simas AM. Synthesis 2000, 1565

6 Athayde-Filho PF. Miller J. Simas AM. Sena KXFR. Chiappeta AA. Acta Farmaceutica Bonaerense 1999, 18: 17

7 Moura GLC. Simas AM. Miller J. Chem. Phys. Lett. 1996, 257: 639

8 Bezerra AGA. Gomes SL. Athayde-Filho PF. da Rocha GB. Miller J. Simas AM. Chem. Phys. Lett. 1999, 309: 421

9 Pretsch E. Clerc T. Seibl J. Simon W. Tabla para la Elucidacion Estructural de Compuestos Orgánicos por Metodos Espectroscopicos Alhambra; Madrid: 1980. p.215

10 Pavia DL. Lampaman GM. Kriz GS. Introduction to Spectroscopy W. R. Saunders Company; London: 1979. p.34

11 Shutske GM. Agnew MN. J. Heterocycl. Chem. 1981, 18: 1025

12 Gilchrist G. In Heterocyclic Chemistry Longman Scientific and Technical Press; New York: 1992. 2nd Ed.. p.15

13 Cheung KK. Echevarria A. Galembeck SE. Maciel MAM. Miller J. Rumjanek VM. Simas AM. Acta Cryst., Sect. C 1992, 48: 1471

14 Bayer HD. Huisgen R. Knorr R. Schaefer FC. Chem. Ber. 1970, 103: 2581

15 Huisgen R. Funke E. Schaefer FC. Gotthardt H. Brunn E. Tetrahedron Lett. 1976, 19: 1809