Original scientific paper

https://doi.org/10.5562/cca2487

The Utility of 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) as a Hydrogen Bond Acceptor in the Design of Novel Superbasic Guanidines – A Computational Study

Vjekoslav Štrukil ; Division of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička cesta 54, 10000 Zagreb, Croatia
Ivana Antol ; Division of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička cesta 54, 10000 Zagreb, Croatia
Zoran Glasovac ; Division of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička cesta 54, 10000 Zagreb, Croatia

Abstract

New guanidine-derived superbases with TBD-functionalized alkyl side chains have been developed using a computational DFT approach. Exploiting the high hydrogen bond basicity of TBD allowed ac-cess to systems with strong charge-assisted intramolecular hydrogen bonds in the protonated state. The enhanced stability of such guanidines is mirrored in their gas-phase basicities, which cover the range from 1044−1168 kJ mol−1, depending on the number of alkyl side chains, the type of alkyl spac-er and the hydrogen-bonding pattern.

Keywords

guanidine; TBD; organic superbases; DFT; intramolecular hydrogen bond

Hrčak ID:

131544

URI

https://hrcak.srce.hr/131544

Publication date:

22.12.2014.

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