Display options
Cite
Bengiat R, Gil M, Klein A, et al. Selective recognition of fluoride salts by vasarenes: a key role of a self-assembled in situ dimeric entity via an exceptionally short [O-H-O](-) H-bond. Dalton Trans. 2016;45(21):8734-9doi: 10.1039/c5dt04171f.
Bengiat, R., Gil, M., Klein, A., Bogoslavsky, B., Cohen, S., Dubnikova, F., Yardeni, G., Zilbermann, I., & Almog, J. (2016). Selective recognition of fluoride salts by vasarenes: a key role of a self-assembled in situ dimeric entity via an exceptionally short [O-H-O](-) H-bond. Dalton transactions (Cambridge, England : 2003), 45(21), 8734-9. https://doi.org/10.1039/c5dt04171f
Bengiat, R, et al. "Selective recognition of fluoride salts by vasarenes: a key role of a self-assembled in situ dimeric entity via an exceptionally short [O-H-O](-) H-bond." Dalton transactions (Cambridge, England : 2003) vol. 45,21 (2016): 8734-9. doi: https://doi.org/10.1039/c5dt04171f
Bengiat R, Gil M, Klein A, Bogoslavsky B, Cohen S, Dubnikova F, Yardeni G, Zilbermann I, Almog J. Selective recognition of fluoride salts by vasarenes: a key role of a self-assembled in situ dimeric entity via an exceptionally short [O-H-O](-) H-bond. Dalton Trans. 2016 Jun 07;45(21):8734-9. doi: 10.1039/c5dt04171f. Epub 2016 Jan 25. PMID: 26804131.
Copy Download .nbib Format: NLM
Share it on

Dalton Trans. 2016 Jun 07;45(21):8734-9. doi: 10.1039/c5dt04171f. Epub 2016 Jan 25.

Selective recognition of fluoride salts by vasarenes: a key role of a self-assembled in situ dimeric entity via an exceptionally short [O-H-O](-) H-bond.

Dalton transactions (Cambridge, England : 2003)

R Bengiat, M Gil, A Klein, B Bogoslavsky, S Cohen, F Dubnikova, G Yardeni, I Zilbermann, J Almog

Affiliations

  1. Institute of Chemistry, The Hebrew University of Jerusalem, Jerusalem, 9190401, Israel. [email protected].

PMID: 26804131 DOI: 10.1039/c5dt04171f

Abstract

A self-assembled supramolecular dimeric entity via an exceptionally short (2.404 Å) and strong (22.9 kcal mol(-1)) [O-H-O](-) hydrogen bond is the key to the special reactivity of vasarenes with fluoride salts. Vasarene is a self-assembled, vase-shaped compound, obtained by the reaction between ninhydrin and phloroglucinol. Analogous compounds are prepared by replacing the phloroglucinol with other polyhydroxy aromatics. Vasarenes show special affinity towards compounds of the type M(+)F(-), where M being a large monovalent cation, producing ion-pair-vasarene adducts. The first step in the proposed mechanism is the dissociation of the M(+)F(-) salt releasing F(-) to the solution, which may provide an explanation as to why only MF salts, which include large monovalent cations, undergo this reaction. From a practical point of view, the ease of their preparation and their special affinity towards fluoride salts make vasarenes potential means for salt separation. The readily formed dimeric structure with the very short [O-H-O](-) negative charge-assisted H-bond (-CAHB) can also be further used as a model in theoretical studies of such systems and understanding their role in biological processes.

Publication Types