Universal prediction of intramolecular hydrogen bonds in organic crystals

Galek, Peter T. A., Fabian, Laszlo and Allen, Frank H. (2010) Universal prediction of intramolecular hydrogen bonds in organic crystals. Acta Crystallographica Section B, 66 (2). pp. 237-252.

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A complete exploration of intramolecular hydrogen bonds (IHBs) has been undertaken using a combination of statistical analyses of the Cambridge Structural Database and computation of ab initio interaction energies for prototypical hydrogen-bonded fragments. Notable correlations have been revealed between computed energies, hydrogen-bond geometries, donor and acceptor chemistry, and frequencies of occurrence. Significantly, we find that 95% of all observed IHBs correspond to the five-, six- or seven-membered rings. Our method to predict a propensity for hydrogen-bond occurrence in a crystal has been adapted for such IHBs, applying topological and chemical descriptors derived from our findings. In contrast to intermolecular hydrogen bonding, it is found that IHBs can be predicted across the complete chemical landscape from a single optimized probability model, which is presented. Predictivity of 85% has been obtained for generic organic structures, which can exceed 90% for discrete classes of IHB.

Item Type: Article
Faculty \ School: Faculty of Science > School of Pharmacy
UEA Research Groups: Faculty of Science > Research Groups > Drug Delivery and Pharmaceutical Materials (former - to 2017)
Faculty of Science > Research Groups > Pharmaceutical Materials and Soft Matter
Depositing User: Rachel Smith
Date Deposited: 15 Mar 2011 16:06
Last Modified: 03 Jan 2023 17:31
URI: https://ueaeprints.uea.ac.uk/id/eprint/26260
DOI: 10.1107/s0108768110003988

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