Dataset curated

DOI:
https://doi.org/10.34804/supra.20210928320 Cc Cc by 4.0

Title:
Complexation of Ferrocene Derivatives by the Cucurbit[7]uril Host:  A Comparative Study of the Cucurbituril and Cyclodextrin Host Families

https://pubs.acs.org/na101/home/literatum/publisher/achs/journals/content/jacsat/2005/jacsat.2005.127.issue-37/ja052912c/production/images/large/ja052912cn00001.jpeg

Description:
The formation of inclusion complexes between cucurbit[7]uril (CB[7]) and ferrocene and its derivatives has been investigated. The X-ray crystal structure of the 1:1 inclusion complex between ferrocene and CB[7] revealed that the guest molecule resides in the host cavity with two different orientations. Inclusion of a set of five water-soluble ferrocene derivatives in CB[7] was investigated by 1H NMR spectroscopy and calorimetric and voltammetric techniques. Our data indicate that all neutral and cationic guests form highly stable inclusion complexes with CB[7], with binding constants in the 109−1010 M-1 and 1012−1013 M-1 ranges, respectively. However, the anionic ferrocenecarboxylate, the only negatively charged guest among those surveyed, was not bound by CB[7] at all. These results are in sharp contrast to the known binding behavior of the same guests to β-cyclodextrin (β-CD), since all the guests form stable inclusion complexes with β-CD, with binding constants in the range 103−104 M-1. The electrostatic surface potentials of CB[6], CB[7], and CB[8] and their size-equivalent CDs were calculated and compared. The CD portals and cavities exhibit low surface potential values, whereas the regions around the carbonyl oxygens in CBs are significantly negative, which explains the strong affinity of CBs for positively charged guests and also provides a rationalization for the rejection of anionic guests. Taken together, our data suggest that cucurbiturils may form very stable complexes. However, the host−guest interactions are very sensitive to some structural features, such as a negatively charged carboxylate group attached to the ferrocene residue, which may completely disrupt the stability of the complexes.

Citation:

A. E. Kaifer, V. Sindelar, M. V. Rekharsky, Y. Inoue, K. Kim, Y. H. Ko, N. Selvapalam, W. S. Jeon, K. Moon, S. H. Park, H. Chun, J. Y. Lee, E. S. Lee, S. Samal, D. Sobransingh, SupraBank 2024, Complexation of Ferrocene Derivatives by the Cucurbit[7]uril Host:  A Comparative Study of the Cucurbituril and Cyclodextrin Host Families (dataset). https://doi.org/10.34804/supra.20210928320

Link: https://doi.org/10.34804/supra.20210928320
Export: BibTex | RIS | EndNote
Views Downloads Citations
2650 0 0
Citation:

W. S. Jeon, K. Moon, S. H. Park, H. Chun, Y. H. Ko, J. Y. Lee, E. S. Lee, S. Samal, N. Selvapalam, M. V. Rekharsky, et al., J. Am. Chem. Soc. 2005, 127, 12984–12989.

Link: https://doi.org/10.1021/ja052912c
Export: BibTex | RIS | EndNote |
Creators:
Orcidid | Ror | Woo Sung Jeon
Orcidid | Ror | Kwangyul Moon
Orcidid | Ror | Sang Hyun Park
Orcidid | Ror | Hyungpil Chun
Orcidid | Ror | Young Ho Ko
Orcidid | Ror | Jin Yong Lee
Orcidid | Ror | Eun Sung Lee
Orcidid | Ror | S. Samal
Orcidid | Ror | N. Selvapalam
Orcidid | Ror | Mikhail V. Rekharsky
Orcidid | Ror | Vladimir Sindelar
Orcidid | Ror | David Sobransingh
Orcidid | Ror | Yoshihisa Inoue
Orcidid | Ror | Angel E. Kaifer
Orcidid | Ror | Kimoon Kim

Contributers:
Orcidid | Ror | Laura Grimm | DataManager

Included Interactions 5 Info

Show interactions per page
Default trans