Issue 12, 2012
From the journal:

Organic & Biomolecular Chemistry

(+)-syn-Benzotriborneol an enantiopure C3-symmetric receptor for water†

Fabrizio Fabris,*a   Ottorino De Lucchi,a   Ilaria Nardini,b   Marco Crisma,c   Andrea Mazzanti,d   Sax A. Mason,e   Marie-Hélène Lemée-Cailleau,e   Francesca A. Scaramuzzof  and  Cristiano Zonta*f  

* Corresponding authors

a Dipartimento di Scienze Molecolari e Nanosistemi, Università Ca’ Foscari di Venezia Dorsoduro 2137, I-30123, Venezia, Italy
E-mail: fabrisfa@unive.it

b Dipartimento di Scienze Ambientali, Informatica e Statistica, Università Ca’ Foscari di Venezia, Via Torino 155/B, I-30174, Mestre, Italy

c Istituto di Chimica Biomolecolare, CNR, Via Marzolo 1, I-35131, Padova, Italy

d Department of Organic Chemistry ‘A. Mangini’, University of Bologna, Viale Risorgimento 4, I-40136, Bologna, Italy

e Institut Laue-Langevin, 6 rue Jules Horowitz, BP 156 38042, Grenoble Cedex 9, France

f Dipartimento di Scienze Chimiche, Università degli Studi di Padova, Via Marzolo 1, I-35131, Padova, Italy
E-mail: cristiano.zonta@unipd.it

Abstract

(+)-syn-Benzotriborneol forms stable complexes with one molecule of water. This is due to the ability of the host to form three hydrogen bonds with water, to act simultaneously as a hydrogen-bond acceptor and donor, and to a perfect geometrical match between the pair. We report experimental (X-ray and neutron diffraction, VT NMR, DSC, TGA) and stereochemical studies carried out to elucidate and quantify the molecular and thermodynamic aspects of this supramolecular complex.

Graphical abstract: (+)-syn-Benzotriborneol an enantiopure C3-symmetric receptor for water

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Article information

DOI
https://doi.org/10.1039/C2OB06774A
Article type
Paper
Submitted
21 Oct 2011
Accepted
16 Jan 2012
First published
17 Jan 2012

Org. Biomol. Chem., 2012,10, 2464-2469

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(+)-syn-Benzotriborneol an enantiopure C3-symmetric receptor for water

F. Fabris, O. De Lucchi, I. Nardini, M. Crisma, A. Mazzanti, S. A. Mason, M. Lemée-Cailleau, F. A. Scaramuzzo and C. Zonta, Org. Biomol. Chem., 2012, 10, 2464 DOI: 10.1039/C2OB06774A

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