Hydrogen bonding in ortho-substituted arylamides: The influence of protic solvents

Zhiwei Liu, Richard C. Remsing, Dahui Liu, Guillermo Moyna, Vojislava Pophristic

Research output: Contribution to journalArticlepeer-review

22 Scopus citations


We combine molecular modeling and NMR methods to better understand intramolecular hydrogen bonding (H-bonding) in a frequently used arylamide foldamer building block, ortho-methoxy-N-methylbenzamide. Our results show that solvents have a profound influence on the cumulative number and stabilizing effects of intramolecular H-bonds, and thus conformational preferences, of foldamers based on this compound. While intramolecular H-bonds are conserved in aprotic environments, they are significantly disrupted in protic solvents. Furthermore, these solvent effects can be accurately quantified using the computational approach presented here. The results could have significant implications in foldamer design, particularly for applications in aqueous environments.

Original languageEnglish (US)
Pages (from-to)7041-7044
Number of pages4
JournalJournal of Physical Chemistry B
Issue number20
StatePublished - May 21 2009
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Physical and Theoretical Chemistry
  • Surfaces, Coatings and Films
  • Materials Chemistry


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