Hydrogen bonding to carbonyl oxygen of nitrogen-pyramidalized amide – detection of pyramidalization direction preference by vibrational circular dichroism spectroscopy. Issue 21 (18th February 2016)

• Record Type: Journal Article
• Authors: Wang, Siyuan; Taniguchi, Tohru; Monde, Kenji; Kawahata, Masatoshi; Yamaguchi, Kentaro; Otani, Yuko; Ohwada, Tomohiko
• Is Part Of: Chemical communications. Volume 52:Issue 21(2016)
• Page Start: 4018
• Page End: 4021
• Publication Date: 2016-02-18
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/c6cc00284f
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : Hydrogen-bonding to carbonyl of nitrogen-pyramidalized bicyclic β-proline amides can switch the preferred nitrogen-pyramidalization direction, as detected by VCD 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.