Affordable Access

Universal prediction of intramolecular hydrogen bonds in organic crystals

Authors
Publication Date
Disciplines
  • Chemistry
  • Mathematics

Abstract

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.

There are no comments yet on this publication. Be the first to share your thoughts.

Statistics

Seen <100 times
0 Comments

More articles like this

Universal prediction of intramolecular hydrogen bo...

on Acta Crystallographica Section... April 2010

[Intramolecular hydrogen bonds and conformation of...

on Antibiotiki i khimioterapii︠a︡... September 1988

Bent OH --- O hydrogen bonds in crystals

on Chemical Physics Letters Jan 01, 1968
More articles like this..