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Croatica Chemica Acta, Vol.87 No.4 Prosinac 2014.

Izvorni znanstveni članak
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

Puni tekst: engleski, pdf (941 KB) str. 423-430 preuzimanja: 536* citiraj
APA
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). doi:10.5562/cca2487

Sažetak
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.

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

Hrčak ID: 131544

URI
http://hrcak.srce.hr/131544

Posjeta: 678 *