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Cyclopropenimine as a hydrogen bond acceptor— towards the strongest non-phosphorus superbases


Barić, Danijela; Dragičević, Ivan; Kovačević, Borislav
Cyclopropenimine as a hydrogen bond acceptor— towards the strongest non-phosphorus superbases // Tetrahedron, 70 (2014), 45; 8571-8576 doi:10.1016/j.tet.2014.09.068 (međunarodna recenzija, članak, znanstveni)


Naslov
Cyclopropenimine as a hydrogen bond acceptor— towards the strongest non-phosphorus superbases

Autori
Barić, Danijela ; Dragičević, Ivan ; Kovačević, Borislav

Izvornik
Tetrahedron (0040-4020) 70 (2014), 45; 8571-8576

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
Organic superbase ; Hydrogen bonds ; DFT calculations ; Proton affinity ; pKa

Sažetak
Utilizing dialkylamino cyclopropenimines as hydrogen bond acceptors in tri-substituted guanidines and cyclopropenimines, we computationally designed the most basic superbases possessing intramolecular hydrogen bonds (IHB-superbases) so far. The values of proton affinity in the gas phase range between 296.6 and 306 kcal mol−1, with estimated pKa values in acetonitrile between 35.5 and 39.7. The obtained PAs of five new IHB-superbases surpass the basicity of the paradigmatic P4-tBu Schwesinger phosphazene, whereas pKa values come close to that of P4-tBu. None of the designed superbases contain phosphorus, which puts them among few most basic non-phosphorus superbases desiged so far.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Projekt / tema
098-0982933-2937 - Računalno proučavanje strukture i funkcije proteina (David Matthew Smith, )

Ustanove
Institut "Ruđer Bošković", Zagreb

Citiraj ovu publikaciju

Barić, Danijela; Dragičević, Ivan; Kovačević, Borislav
Cyclopropenimine as a hydrogen bond acceptor— towards the strongest non-phosphorus superbases // Tetrahedron, 70 (2014), 45; 8571-8576 doi:10.1016/j.tet.2014.09.068 (međunarodna recenzija, članak, znanstveni)
Barić, D., Dragičević, I. & Kovačević, B. (2014) Cyclopropenimine as a hydrogen bond acceptor— towards the strongest non-phosphorus superbases. Tetrahedron, 70 (45), 8571-8576 doi:10.1016/j.tet.2014.09.068.
@article{article, year = {2014}, pages = {8571-8576}, DOI = {10.1016/j.tet.2014.09.068}, keywords = {Organic superbase, Hydrogen bonds, DFT calculations, Proton affinity, pKa}, journal = {Tetrahedron}, doi = {10.1016/j.tet.2014.09.068}, volume = {70}, number = {45}, issn = {0040-4020}, title = {Cyclopropenimine as a hydrogen bond acceptor— towards the strongest non-phosphorus superbases}, keyword = {Organic superbase, Hydrogen bonds, DFT calculations, Proton affinity, pKa} }

Časopis indeksira:


  • Current Contents Connect (CCC)
  • Web of Science Core Collection (WoSCC)
    • Science Citation Index Expanded (SCI-EXP)
    • SCI-EXP, SSCI i/ili A&HCI
  • Scopus


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