The Synthesis and Structural Characterization of Peralkylated Triguanide Superbases

Vjekoslav Štrukil; Edislav Lekšić; Ernest Meštrović; Mirjana Eckert-Maksić

doi:10.1071/CH14233

RESEARCH ARTICLE

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The Synthesis and Structural Characterization of Peralkylated Triguanide Superbases

Vjekoslav Štrukil ^A , Edislav Lekšić ^B , Ernest Meštrović ^B and Mirjana Eckert-Maksić ^A ^C

+ Author Affiliations

- Author Affiliations

^A Division of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička cesta 54, 10000 Zagreb, Croatia.

^B Pliva TAPI, Prilaz Baruna Filipovića 29, 10000 Zagreb, Croatia.

^C Corresponding author. Email: mmaksic@emma.irb.hr

Australian Journal of Chemistry 67(7) 1129-1133 https://doi.org/10.1071/CH14233
Submitted: 10 April 2014 Accepted: 20 May 2014 Published: 12 June 2014

Abstract

Organic superbases derived from a peralkylated triguanide framework have been synthesized in a coupling reaction between monosubstituted guanidines and a Vilsmeier salt. Single crystal X-ray diffraction analysis of the chloride salt allowed the structural characterization of the benzyl derivative for the first time and revealed an effective delocalization of the positive charge despite significant distortion of the triguanide cation planarity. With the calculated gas phase basicity ranging from 262 to 265 kcal mol^–1 and pK_a values in acetonitrile between 28 and 30, these compounds have been evaluated as potential organocatalysts in the transesterification reaction of vegetable oil.

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The Synthesis and Structural Characterization of Peralkylated Triguanide Superbases

Abstract

References

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