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Substituted troponimines: when aromatization of the conjugate acid leads to very strong neutral organic superbases

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Abstract

In the present study, N-methyl-2,4,6-cycloheptatriene-1-imine (troponimine) with (Me)2N- and MeO-substituents has been investigated theoretically to evaluate its suitability as a new neutral organic superbase. To introduce the aforementioned system, thermochemical parameters such as gas basicity and proton affinity have been calculated along with pKBH+ values in acetonitrile. The results revealed that all of the studied troponimine derivatives were more basic than 1,8-bis(dimethylamino)-naphthalene whose gas phase basicity of 237 kcal mol−1 is considered to be the borderline between ordinary bases and superbases. However, the most important finding was that some of the proposed troponimines were much stronger bases than the well-established cyclopropenimine superbases. The origin of troponimine basicity was elucidated through NICS calculations which revealed that the troponimines become aromatic upon protonation. AIM analyses revealed that a hydrogen bond could also contribute to the basicity if a suitable substituent is located adjacent to the imine group of the troponimine.

Graphical abstract: Substituted troponimines: when aromatization of the conjugate acid leads to very strong neutral organic superbases

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Publication details

The article was received on 12 May 2018, accepted on 12 Jul 2018 and first published on 14 Jul 2018


Article type: Paper
DOI: 10.1039/C8NJ02349B
Citation: New J. Chem., 2018, Advance Article
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    Substituted troponimines: when aromatization of the conjugate acid leads to very strong neutral organic superbases

    K. Saadat, A. Shiri and B. Kovačević, New J. Chem., 2018, Advance Article , DOI: 10.1039/C8NJ02349B

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