Jump to main content
Jump to site search

Issue 23, 2014
Previous Article Next Article

A combined experimental-computational study of benzoxaborole crystal structures

Author affiliations

Abstract

Benzoxaboroles are organoboron molecules which are gaining growing interest in different fields, notably for the development of new drugs. However, extensive characterization of these molecules in the solid state is still lacking. Here, questions related to the structure and spectroscopic signatures of crystalline benzoxaborole phases are thus addressed, using a combined experimental-computational approach. Two simple benzoxaboroles were studied: 1,3-dihydro-1-hydroxy-2,1-benzoxaborole (denoted as BBzx) and 5-fluoro-1,3-dihydro-1-hydroxy-2,1-benzoxaborole (also referred to as AN2690, a newly developed antifungal drug). First, the crystal structures of AN2690 and BBzx at room temperature are discussed, emphasizing the intermolecular interactions which play an important role in their formation. Then, results of IR and multinuclear (1H, 11B, 13C and 19F) solid state NMR characterization are presented, together with density functional theory (DFT) calculations which were carried out to assist in the interpretation of the spectra. Finally, the influence of polymorphism and anisotropic thermal expansion properties of the crystal structures on the NMR parameters of BBzx and AN2690 is discussed.

Graphical abstract: A combined experimental-computational study of benzoxaborole crystal structures

Back to tab navigation

Supplementary files

Publication details

The article was received on 11 Feb 2014, accepted on 18 Mar 2014 and first published on 20 Mar 2014


Article type: Paper
DOI: 10.1039/C4CE00313F
CrystEngComm, 2014,16, 4999-5011

  •   Request permissions

    A combined experimental-computational study of benzoxaborole crystal structures

    S. Sene, D. Berthomieu, B. Donnadieu, S. Richeter, J. Vezzani, D. Granier, S. Bégu, H. Mutin, C. Gervais and D. Laurencin, CrystEngComm, 2014, 16, 4999
    DOI: 10.1039/C4CE00313F

Search articles by author

Spotlight

Advertisements