Effect of a Rigid Sulfonamide Bond on Molecular Folding: A Case Study
Abstract
A disulfonamide compound with bulky aromatic side chains was prepared, and its properties as a potential building block for foldamers were evaluated. Two different solvate crystal forms of the compound were identified and compared to the structures of an analogous oligoamide and related disulfonamides. The disulfonamide is unfolded in one of the solvates, whereas in the other one, a loosely folded conformer stabilized by an intramolecular hydrogen bond is found. Density functional calculations indicated that the loosely folded conformer is slightly more stable than its unfolded isomer. The calculations also identified a third, more tightly folded and more extensively hydrogen bonded, conformer that is even lower in energy.
Main Authors
Format
Articles
Research article
Published
2015
Series
Subjects
Publication in research information system
Publisher
American Chemical Society
The permanent address of the publication
https://urn.fi/URN:NBN:fi:jyu-201506082224Käytä tätä linkitykseen.
Review status
Peer reviewed
ISSN
1528-7483
DOI
https://doi.org/10.1021/acs.cgd.5b00424
Language
English
Published in
Crystal Growth and Design
Citation
- Suhonen, A., Morgan, I., Nauha, E., Helttunen, K., Tuononen, H., & Nissinen, M. (2015). Effect of a Rigid Sulfonamide Bond on Molecular Folding: A Case Study. Crystal Growth and Design, 15(6), 2602-2608. https://doi.org/10.1021/acs.cgd.5b00424
License
Copyright© 2015 American Chemical Society. This is a final draft version of an article whose final and definitive form has been published by ACS. Published in this repository with the kind permission of the publisher.