Abstract
“All good proton donors and acceptors are used in hydrogen bonding” (M. C. Etter, Acc. Chem. Res., 1990, 23, 120–126). This is Margaret Etter's first rule, part of pioneering work which has proven both insightful and accurate over the intervening 20 years since its publication. In this work we question whether a good donor or acceptor can be identified solely from a chemical perspective, e.g. given only a chemical diagram. Results indicate that 2.5% of the organic structures in the Cambridge Structural Database which contain what would be considered a strong donor and an acceptor do not hydrogen bond. We have revealed in 2/3 of the cases, donors or acceptors with reduced accessible surface are responsible i.e. due to steric crowding by neighbouring atoms. We have further identified significant contrasts in the extent to which the degree of inaccessibility affects different donor and acceptor groups. This function-specific behaviour has been characterised in a predictive fashion. In the remaining structures we have also identified a number of other, more specific prohibitive factors. The results of this study will significantly enhance our ability to predict hydrogen-bonds in the future.
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Disclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.