Preparation of a new receptor for anions, macrocyclic polythiolactam - Structure and high anion-binding ability

Tetrahedron Letters

Volumn 44, Issue 28, 2003, Pages 5167-5169

  Inoue, Yoshihiko ^a   Kanbara, Takaki ^a   Yamamoto, Takakazu ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Hydrogen bond; Macrocycle; Neutral anion receptor; Thioamide; Thiocarbonylation

Indexed keywords

ANION; CHLORIDE ION; LACTAM DERIVATIVE; MACROCYCLIC COMPOUND; POLYTHIOLACTAM; RECEPTOR; TETRALACTAM; TETRATHIOLACTAM; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; HYDROGEN BOND; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION;

EID: 0038007914     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01271-1     Document Type: Article

References (32)

1. Beer P.D., Gale P.A. Angew. Chem., Int. Ed. 40:2001;487-516.
2. Gale P.A. Coord. Chem. Rev. 199:2000;181-233.
3. Beer P.D. Acc. Chem. Res. 31:1998;71-80.
4. Bühlmann P., Pretsch E., Bakker E. Chem. Rev. 98:1998;1593-1687.
5. Schmidtchen F.P., Berger M. Chem. Rev. 97:1997;1609-1646.
6. Beer P.D. Chem. Commun. 1996;689-696.
7. de Silva A.P., Gunaratne H.Q.N., Gunnlaugsson T., Huxley A.J.M., McCoy C.P., Rademacher J.T., Rice T.E. Chem. Rev. 97:1997;1515-1566.
8. Snowden T.S., Anslyn E.V. Curr. Opin. Chem. Biol. 3:1999;740-746.
9. Gale P.A. Coord. Chem. Rev. 213:2001;79-128.
10. Sessler J.L., Davis J.M. Acc. Chem. Res. 34:2001;989-997.
11. Bisson A.P., Lynch V.M., Monahan M.-K.C., Anslyn E.V. Angew. Chem., Int. Ed. Engl. 36:1997;2340-2342.
12. Kim Y.H., Calabrese J., McEwen C. J. Am. Chem. Soc. 118:1996;1545-1546.
13. Szumna A., Jurczak J. Eur. J. Org. Chem. 2001;4031-4039.
14. Choi K., Hamilton A.D. J. Am. Chem. Soc. 123:2001;2456-2457.
15. Jagessar R.C., Burns D.H. Chem. Commun. 1997;1685-1686.
16. Gale P.A., Camiolo S., Tizzard G.J., Chapman C.P., Light M.E., Coles S.J., Hursthouse M.B. J. Org. Chem. 66:2001;7849-7853.
17. Navakhun K., Gale P.A., Camiolo S., Light M.E., Hursthouse M.B. Chem. Commun. 2002;2084-2085.
18. Kubik S., Kirchner R., Dolting D., Seidel J. J. Am. Chem. Soc. 124:2002;12752-12760.
19. It is known that the association constant of thiourea to oxoanion is higher than that of the corresponding urea derivative; see (a) Linton, B. R.; Goodman, M. S.; Fan, E.; van Arman, S. A.; Hamilton, A. D. J. Org. Chem. 2001, 66, 7313-7319; (b) Ayling, A. J.; Pérez-Payán, M. N.; Davis, A. P. J. Am. Chem. Soc. 2001, 123, 12716-12717; (c) Herges, R.; Dikmans, A.; Jana, U.; Köhler, F.; Jones, P. G.; Dix, I.; Fricke, T.; König, B. Eur. J. Org. Chem. 2002, 3004-3014.
20. It is known that the association constant of thiourea to oxoanion is higher than that of the corresponding urea derivative; see (a) Linton, B. R.; Goodman, M. S.; Fan, E.; van Arman, S. A.; Hamilton, A. D. J. Org. Chem. 2001, 66, 7313-7319; (b) Ayling, A. J.; Pérez-Payán, M. N.; Davis, A. P. J. Am. Chem. Soc. 2001, 123, 12716-12717; (c) Herges, R.; Dikmans, A.; Jana, U.; Köhler, F.; Jones, P. G.; Dix, I.; Fricke, T.; König, B. Eur. J. Org. Chem. 2002, 3004-3014.
21. It is known that the association constant of thiourea to oxoanion is higher than that of the corresponding urea derivative; see (a) Linton, B. R.; Goodman, M. S.; Fan, E.; van Arman, S. A.; Hamilton, A. D. J. Org. Chem. 2001, 66, 7313-7319; (b) Ayling, A. J.; Pérez-Payán, M. N.; Davis, A. P. J. Am. Chem. Soc. 2001, 123, 12716-12717; (c) Herges, R.; Dikmans, A.; Jana, U.; Köhler, F.; Jones, P. G.; Dix, I.; Fricke, T.; König, B. Eur. J. Org. Chem. 2002, 3004-3014.
22. Shaw R.A., Kokkát E., Hollósi M., Mantsch H.H. Spectrochim. Acta Part A. 51:1995;1399-1412.
23. Laurence C., Berthelot M., Le Questel J.-Y., El Ghomari M.L. J. Chem. Soc., Perkin Trans. 2. 1995;2075-2079.
24. Artis D.R., Lipton M.A. J. Am. Chem. Soc. 120:1998;12200-12206.
25. Lee H.-J., Choi Y.-S., Lee K.-B., Park J., Yoon C.-J. J. Phys. Chem. A. 106:2002;7010-7017.
26. Yde B., Yousif N.M., Pedersen U., Thomsen I., Lawesson S.-O. Tetrahedron. 40:1984;2047-2052.
27. Delêtre M., Levesque G. Macromolecules. 23:1990;4876-4878.
28. 4: C, 48.40; H, 4.06; N, 18.82; S, 28.72. Found: C, 48.10; H, 4.22; N, 17.98; S, 28.14%.
29. -1, T=113 K, F(000)=632. A total of 13800 reflections were measured, 4087 unique. The structure was solved by direct method (SIR-88) and expanded using Fourier techniques. The non-hydrogen atoms were refined anisotoropically. The hydrogen atoms were refined using a riding model. The final cycle of full-matrix least squares refinement on F was based on 3697 observed reflections (I>3σ(I), 220 valuable parameters) with factors of R=0.043, Rw=0.070, GOF=0.85.
30. 6 solution of 2 (5.7 mM) with aliquots of salt solution. We used non-linear least-squares regression for curve fitting. Although we obtained good fit of 1:1 binding isotherms to the titration experimental data in all most of all cases, the possibility of 2:1 ( 2:anion) complex formation could also be considered. See: Hynes M.J. J. Chem. Soc., Dalton Trans. 1993;311-312.
31. Steiner T. Angew. Chem., Int. Ed. 41:2002;48-76.
32. -1, T=113 K, F(000)=856. A total of 39203 reflections were measured, 8342 unique. The structure was solved by direct method (SIR-92) and expanded using Fourier techniques. The non-hydrogen atoms were refined anisotoropically. The hydrogen atoms were refined using a riding model. The final cycle of full-matrix least squares refinement on F was based on 5306 observed reflections (I>3σ(I), 525 valuable parameters) with factors of R=0.056, Rw=0.079, GOF=0.95.