The proton affinity of the superbase 1,8-bis(tetramethylguanidino)naphthalene (TMGN) and some related compounds: a theoretical study

Chemistry : a European Journal
Borislav Kovacević, Zvonimir B Maksić

Abstract

The spatial and electronic structure of the very strong neutral organic bases bis(tetramethylguanidino)naphthalene (TMGN), 4,5-bis(tetramethylguanidino)fluorene (TMGF) and some related compounds are explored by ab initio computational methods. Their affinity towards the proton is scrutinized both in the gas phase and in solution in acetonitrile. The protonation at the most basic center (the imine nitrogen) yields asymmetric and relatively strong intramolecular hydrogen bonds (IHB). It is found that the angular strain effect and steric repulsion practically vanish in TMGN which implies that its high absolute proton affinity (APA) has its origin in the inherent basicity of the guanidine fragment and a relatively strong IHB in [TMGN]H(+). The nonbonded repulsions in TMGF are higher than in TMGN, which in conjunction with a slightly stronger IHB in the corresponding conjugate acid makes it more basic: APA(TMGF)>APA(TMGN). An interesting new phenomenon is observed in both TMGN and TMGF: the proton triggers the resonance stabilization not only in the directly bonded guanidine moiety, but also in the other guanidine fragment which is more distant from the proton, albeit in a less pronounced manner. The latter feature is termed a parti...Continue Reading

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Citations

Jan 8, 2013·Journal of Molecular Modeling·Otilia MóJosé Elguero
Jun 9, 2016·Mass Spectrometry Reviews·Guy Bouchoux, Mirjana Eckert-Maksic
Mar 1, 2013·The Journal of Organic Chemistry·Danijela BarićBorislav Kovačević
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Apr 21, 2017·Dalton Transactions : an International Journal of Inorganic Chemistry·A Paige Lathem, Zachariah M Heiden
Dec 3, 2016·Chemistry : a European Journal·Abul Kalam Biswas, Bishwajit Ganguly
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Jan 27, 2007·The Journal of Organic Chemistry·Roman I ZubatyukJerzy Leszczynski

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