Conformational control of N-methyl-N,N′-diacylhydrazines by noncovalent carbon bonding in solution

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)MIDLINE HORIZONTAL ELLIPSISC-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.