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Issue 20, 2019
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Positively and negatively charged NHN hydrogen bonds in one molecule: synergistic strengthening effect, superbasicity and acetonitrile capture

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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

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Publication details

The article was received on 22 Feb 2019, accepted on 15 Apr 2019 and first published on 23 Apr 2019


Article type: Letter
DOI: 10.1039/C9NJ00965E
New J. Chem., 2019,43, 7557-7561

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    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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