Conformational control of <i>N</i>-methyl-<i>N</i>,<i>N</i>′-diacylhydrazines by noncovalent carbon bonding in solution
Jugal Kishore Deka, Biswajit Sahariah, Kalpita Baruah, Arun Kumar Bar, Bani Kanta Sarma
Abstract
In recent years, some X-ray structural and computational evidence has emerged for noncovalent carbon bonding (C-bond). However, evidence of C-bonds in solution is limited. Herein, from the conformational analyses of strategically designed N-methyl-N,N'-diacylhydrazines, we for the first time show that C-bonds can be modulated to control the conformational preferences of small molecules in solution. We show that unusual N(amide)C-X noncovalent carbon bonding interactions stabilize the trans-cis (t-c) amide bond rotamers of N-methyl-N,N'-diacylhydrazines over the expected trans-trans (t-t) rotamers.
Topics & Concepts
ChemistryCrystallography and molecular interactionsStructural and Chemical Analysis of Organic and Inorganic CompoundsSynthesis of heterocyclic compounds