1,5,7-Triazabicyclo[4.4.0]dec-5-ene

Huczyński, Adam; Brzeziński, Bogumił

doi:10.1002/047084289x.rn00786

Cited by 1 publication

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“…TBD is an organic soluble base (p K a = 25.98 in CH 3 CN and p K a = 21.00 in THF) which has been used effectively for a variety of base-mediated organic transformations . It easily forms hydrogen-bonded crystalline complexes with carboxylic acids, phenols, and C–H acids. − …”

Section: Introductionmentioning

confidence: 99%

“…In our previous paper we showed that strong N- bases such as 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) can be considered as very interesting agents in designing molecular systems for crystal engineering and for studies of the proton transfer reactions and formation of hydrogen-bonded complexes with organic acids. − The hydrogen bond based design of molecular networks has emerged as a powerful tool in the discovery of new materials; therefore, we applied it to study the new salt formed between TBD and dipicrylamine (DPA).…”

Section: Introductionmentioning

confidence: 99%

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X-ray Crystallographic, FT-IR, and Density Functional Theory Studies of the Salt Formed between Dipicrylamine and 1,5,7-Triazabicyclo[4.4.0]dec-1-ene

Huczyński

Janczak²,

Hoffmann³

et al. 2011

J. Phys. Chem. A

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The DPA-TBD (dipicrylamine-1,5,7-triazabicyclo[4.4.0]dec-1-ene) salt has been synthesized and characterized by FT-IR spectroscopy, X-ray single-crystal diffraction, and theoretical study. In the FT-IR spectrum of the crystalline DPA-TBD salt, an unexpected intense band at 1742 cm(-1) is present. The optimized geometry and the FT-IR spectra of the DPA salt were calculated at the B3LYP/6-31G+(d) level and give an explanation of the nature of this band as the ν(C═N═C) vibration. For comparison, the calculated IR spectra of the DPA anion, hydrogen-bonded DPA anion, and neutral DPA and TBD molecules as well as for the TBD cation are also shown. The presence of the free DPA anion in the gas phase was directly detected in the negative ion mode electrospray ionization MS spectra. The fragmentation of the DPA anion is also discussed.

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