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Pregled bibliografske jedinice broj: 671039

A New Synthetic Pathway to the Second and Third Generation of Superbasic Bisphosphazene Proton Sponges : The Run for the Best Chelating Ligand for a Proton

Kögel, Julius F; Oelkers, Benjamin; Kovačević, Borislav; Sundermeyer, Jörg
A New Synthetic Pathway to the Second and Third Generation of Superbasic Bisphosphazene Proton Sponges : The Run for the Best Chelating Ligand for a Proton // Journal of the American Chemical Society, 35 (2013), 47; 17768-17774 doi:10.1021/ja409760z (međunarodna recenzija, članak, znanstveni)

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Naslov
A New Synthetic Pathway to the Second and Third Generation of Superbasic Bisphosphazene Proton Sponges : The Run for the Best Chelating Ligand for a Proton

Autori
Kögel, Julius F ; Oelkers, Benjamin ; Kovačević, Borislav ; Sundermeyer, Jörg

Izvornik
Journal of the American Chemical Society (0002-7863) 35 (2013), 47; 17768-17774

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

Ključne riječi
proton sponge; superbase

Sažetak
We present the up to now strongest chelating neutral pincer ligand for the simplest electrophile of chemistry, the proton. Two novel bisphosphazene proton sponges, 1, 8-bis(trispyrrolidinophosphazenyl)naphthalene (TPPN) and its higher homologue P2-TPPN, were obtained via a Staudinger reaction and investigated concerning their structural features and basic properties by experimental and computational means. They exhibit experimental pKBH+ values in acetonitrile of 32.3 and 42.1, respectively, exceeding the existing basicitiy record for proton sponges by more than 10 orders of magnitude. We show that Schwesinger’s concept of homologization of phosphazene bases and Alder’s concept of proton chelation in a constrained geometry regime of basic centers can be combined in the design of highly basic nonionic superbases of pincer type.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA

Projekti:
098-0982933-2937 - Računalno proučavanje strukture i funkcije proteina (Smith, David Matthew, MZOS ) ( CroRIS)

Ustanove:
Institut "Ruđer Bošković", Zagreb

Profili:

Avatar Url Borislav Kovačević (autor)

Poveznice na cjeloviti tekst rada:

doi pubs.acs.org

Citiraj ovu publikaciju:

Kögel, Julius F; Oelkers, Benjamin; Kovačević, Borislav; Sundermeyer, Jörg
A New Synthetic Pathway to the Second and Third Generation of Superbasic Bisphosphazene Proton Sponges : The Run for the Best Chelating Ligand for a Proton // Journal of the American Chemical Society, 35 (2013), 47; 17768-17774 doi:10.1021/ja409760z (međunarodna recenzija, članak, znanstveni)
Kögel, J., Oelkers, B., Kovačević, B. & Sundermeyer, J. (2013) A New Synthetic Pathway to the Second and Third Generation of Superbasic Bisphosphazene Proton Sponges : The Run for the Best Chelating Ligand for a Proton. Journal of the American Chemical Society, 35 (47), 17768-17774 doi:10.1021/ja409760z.
@article{article, author = {K\"{o}gel, Julius F and Oelkers, Benjamin and Kova\v{c}evi\'{c}, Borislav and Sundermeyer, J\"{o}rg}, year = {2013}, pages = {17768-17774}, DOI = {10.1021/ja409760z}, keywords = {proton sponge, superbase}, journal = {Journal of the American Chemical Society}, doi = {10.1021/ja409760z}, volume = {35}, number = {47}, issn = {0002-7863}, title = {A New Synthetic Pathway to the Second and Third Generation of Superbasic Bisphosphazene Proton Sponges : The Run for the Best Chelating Ligand for a Proton}, keyword = {proton sponge, superbase} }
@article{article, author = {K\"{o}gel, Julius F and Oelkers, Benjamin and Kova\v{c}evi\'{c}, Borislav and Sundermeyer, J\"{o}rg}, year = {2013}, pages = {17768-17774}, DOI = {10.1021/ja409760z}, keywords = {proton sponge, superbase}, journal = {Journal of the American Chemical Society}, doi = {10.1021/ja409760z}, volume = {35}, number = {47}, issn = {0002-7863}, title = {A New Synthetic Pathway to the Second and Third Generation of Superbasic Bisphosphazene Proton Sponges : The Run for the Best Chelating Ligand for a Proton}, keyword = {proton sponge, superbase} }

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

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