Issue 20, 2019

Positively and negatively charged NHN hydrogen bonds in one molecule: synergistic strengthening effect, superbasicity and acetonitrile capture

Abstract

The first zwitterions with [NHN]+ and [NHN] intramolecular hydrogen bonds have been studied. Due to their mutual reinforcement, shortening of N⋯N distances in both NHN subunits (up to 2.546 Å) occurs in symmetrical zwitterion 12. Being less acidic, the [NHN] bridge makes the [NHN]+ part harder to disrupt, thus rendering 12 superbasic and recognition properties.

Graphical abstract: Positively and negatively charged NHN hydrogen bonds in one molecule: synergistic strengthening effect, superbasicity and acetonitrile capture

Supplementary files

Article information

Article type
Letter
Submitted
22 Feb 2019
Accepted
15 Apr 2019
First published
23 Apr 2019

New J. Chem., 2019,43, 7557-7561

Positively and negatively charged NHN hydrogen bonds in one molecule: synergistic strengthening effect, superbasicity and acetonitrile capture

M. P. Vlasenko, V. A. Ozeryanskii, A. F. Pozharskii and O. V. Khoroshilova, New J. Chem., 2019, 43, 7557 DOI: 10.1039/C9NJ00965E

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