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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

Fulltext: english, pdf (941 KB) pages 423-430 downloads: 912* cite
APA 6th Edition
Štrukil, V., Antol, I. & Glasovac, Z. (2014). 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. Croatica Chemica Acta, 87 (4), 423-430. https://doi.org/10.5562/cca2487
MLA 8th Edition
Štrukil, Vjekoslav, et al. "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." Croatica Chemica Acta, vol. 87, no. 4, 2014, pp. 423-430. https://doi.org/10.5562/cca2487. Accessed 9 Jul. 2020.
Chicago 17th Edition
Štrukil, Vjekoslav, Ivana Antol and Zoran Glasovac. "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." Croatica Chemica Acta 87, no. 4 (2014): 423-430. https://doi.org/10.5562/cca2487
Harvard
Štrukil, V., Antol, I., and Glasovac, Z. (2014). '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', Croatica Chemica Acta, 87(4), pp. 423-430. https://doi.org/10.5562/cca2487
Vancouver
Štrukil V, Antol I, Glasovac Z. 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. Croatica Chemica Acta [Internet]. 2014 [cited 2020 July 09];87(4):423-430. https://doi.org/10.5562/cca2487
IEEE
V. Štrukil, I. Antol and Z. Glasovac, "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", Croatica Chemica Acta, vol.87, no. 4, pp. 423-430, 2014. [Online]. https://doi.org/10.5562/cca2487

Abstracts
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

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