Issue 21, 2016

Hydrogen bonding to carbonyl oxygen of nitrogen-pyramidalized amide – detection of pyramidalization direction preference by vibrational circular dichroism spectroscopy

Abstract

Nitrogen-pyramidalization of amide increases electron density on nitrogen and decreases that on carbonyl oxygen. We identified hydrogen-bonding to carbonyl of nitrogen-pyramidalized bicyclic β-proline derivatives by crystallography, and by NMR and vibrational circular dichroism (VCD) spectroscopy in solution. Such hydrogen-bonding can switch the preferred nitrogen-pyramidalization direction, as detected by VCD spectroscopy.

Graphical abstract: Hydrogen bonding to carbonyl oxygen of nitrogen-pyramidalized amide – detection of pyramidalization direction preference by vibrational circular dichroism spectroscopy

  • This article is part of the themed collection: Foldamers

Supplementary files

Article information

Article type
Communication
Submitted
12 Janv. 2016
Accepted
12 Febr. 2016
First published
18 Febr. 2016
This article is Open Access
Creative Commons BY license

Chem. Commun., 2016,52, 4018-4021

Hydrogen bonding to carbonyl oxygen of nitrogen-pyramidalized amide – detection of pyramidalization direction preference by vibrational circular dichroism spectroscopy

S. Wang, T. Taniguchi, K. Monde, M. Kawahata, K. Yamaguchi, Y. Otani and T. Ohwada, Chem. Commun., 2016, 52, 4018 DOI: 10.1039/C6CC00284F

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