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

Štrukil, Vjekoslav; Antol, Ivana; Glasovac, Zoran (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. ISSN 0011-1643

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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 access 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 spacer and the hydrogen-bonding pattern.

Item Type:	Article
Uncontrolled Keywords:	guanidine, TBD, organic superbases, DFT, intramolelcular hydrogen bond
Subjects:	NATURAL SCIENCES > Chemistry
Divisions:	Division of Organic Chemistry and Biochemistry
Projects:	Project title Project leader Project code Project type Organski i bioorganski procesi u osnovnom i elektronski pobuđenim stanjima [27544] Mirjana Maksić 098-0982933-2920 MZOS
Depositing User:	Sofija Konjević
Date Deposited:	10 Mar 2015 14:11
URI:	http://fulir.irb.hr/id/eprint/1712
DOI:	10.5562/cca2487

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