Abstract
The inclusion complexes of 2-naphthyloxyacetic acid (NOA) and 1-naphthylacetic acid (NAA) with β-cyclodextrin have been investigated in aqueous solution. It has been demonstrated that the naphthalene derivatives form 1:1 complexes when included in the cyclodextrin. A possible structure is proposed, having an axial inclusion of the naphthalene derivatives. In the case of the β-CD: NOA complex, the naphthyl moiety is included in the cyclodextrin and the acetic acid group protrudes from the cavity, while NAA is only partially included because of the steric effect of the group in position 1. Association constants of 560±100 M−1 and 100±50 M−1 have been calculated for the β-CD: NOA and β-CD: NAA complexes, making use of the increment in the fluorescene emission produced in the inclusion process.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
J. Szeijtli:Cyclodextrins and Their Inclusion Compounds, Akademiai Kiado, Budapest (1982).
J. Szeijtli:Pharm. Technol. Int. 3, 15 (1991).
J. Szeijtli:Cyclodextrin Technology, Kluwer, Dordrecht (1988).
D. Duchene (Ed.):Cyclodextrins and Their Industrial Uses, Ed. de Santé, Paris (1987).
a. Muñoz de la Peña, T. T. Ndou, J. B. Zung, K. L. Greene, D. H. Live, and I. M. Warner:J. Am. Chem. Soc. 113, 1572 (1991).
A. Muñoz de la Peña, T. T. Ndou, J. B. Zung, and I. M. Warner:J. Phys. Chem. 95, 3330 (1991).
A. Muñoz de la Peña, V. Anigbogu, T. T. Ndou, and I. M. Warner:Anal. Chem. 63, 1018 (1991).
J. M. Schuette, T. Ndou, A. Muñoz de la Peña, K. L. Greene, C. K. Williamson, and I. M. Warner:J. Phys. Chem. 95, 4897 (1991).
V. K. Smith, T. T. Ndou, A. Muñoz de la Peña, and I. M. Warner:J. Incl. Phenom. 10, 471 (1991).
J. B. Zung, A. Muñoz de la Peña, T. Ndou, and I. M. Warner:J. Phys. Chem. 95, 6701 (1991).
V. Anigbogu, A. Muñoz de la Peña, T. T. Ndou, and I. M. Warner:Anal. Chem. 64, 484 (1991).
S. Hamai:Bull. Chem. Soc. Jpn. 55, 2721 (1982).
S. Hashimoto and J. K. Thomas:J. Am. Chem. Soc. 107, 4655 (1985).
G. Nelson and I. M. Warner:J. Phys. Chem. 94, 576 (1990).
G. Nelson, G. Patonay and I. M. Warner:Appl. Spectrosc. 41, 1235 (1987).
C. D. Tran and J. H. Fendler:J. Phys. Chem. 88, 2167 (1984).
K. Harata and H. Uedaira:Bull. Chem. Soc. Jpn. 48, 375 (1975).
K. Kano, I. Takenoshita, and T. Ogawa:Chem. Lett. 1035 (1980).
K. Kano, I. Takenoshita, and T. Ogawa:J. Phys. Chem. 86, 1833 (1982).
T. Yorozu, M. Hoshino, M. Imamura, and H. Shizuka:J. Phys. Chem. 86, 4422 (1982).
J. C. Márquez, M. Hernandez, and F. Carcía Sánchez:Analyst 115, 1003 (1990).
D. A. Lerner, B. Del Castillo, and S. Muñoz Botella:Anal. Chim. Acta 227, 297 (1989).
O. Jules, S. Scypinski and L. J. Cline Love:Anal. Chim. Acta 169, 335 (1985).
W. Baeyens, B. Lin and V. Corbisier:Analyst 115, 359 (1990).
W. Baeyens, B. L. Ling, V. Corbisier, and A. Raemdonck:Anal. Chim. Acta 234, 187 (1990).
S. Scypinski and L. J. Cline Love:Anal. Chem. 56, 322 (1984).
S. Scypinski and L. J. Cline Love:Anal. Chem. 56, 331 (1984).
H. J. Casal, J. C. Netto-Ferreira, and J. C. Scaiano:J. Incl. Phenom. 3, 395 (1985).
S. Hamai:J. Am. Chem. Soc. 111, 3954 (1989).
A. Muñoz de la Peña, I. Durán-Merás, F. Salinas, T. T. Ndou, and I. M. Warner:Anal. Chim. Acta 255, 351 (1991).
K. A. Connors:Binding Constants, the Measurement of Molecular Complex Stability, John Wiley & Sons, New York (1987).
C. D. Gutsche:Calixarenes, p. 184, The Royal Society of Chemistry, Cambridge (1989).
C. Catena and F. V. Bright:Anal. Chem. 61, 905 (1989).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
de la Peña, A.M., Salanas, F., Gómez, M.J. et al. Absorptiometric and spectrofluorimetric study of the inclusion complexes of 2-naphthyloxyacetic acid and 1-naphthylacetic acid with β-cyclodextrin in aqueous solution. J Incl Phenom Macrocycl Chem 15, 131–143 (1993). https://doi.org/10.1007/BF00710222
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF00710222