P[N(iBu)CH2CH2]3N: A versatile non-ionic base for the synthesis of higher coordinate silicates

Kingston, J. V.; Verkade, John G.

doi:10.1016/j.inoche.2005.04.009

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Other Phosphorus Containing Superbases: Verkades Proazaphosp1

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Cited by 10 publications

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“…In contrast to proazaphosphatranes, azaphosphatranes 139 have oblate frameworks that feature a trans-annular N-P bond in the [3.3.3] tricyclic cage, as in the case of cations in which the PN 3 end of the proazaphosphatrane is flattened and its bottom is puckered upward. The approximately 3 A bridgehead-bridgehead transannular N ax -P distance in 138 thus shortens to about 2 A in azaphosphatranes [98]. Basicity measurements have shown that proazaphosphatranes are exceedingly strong nonionic Brønsted bases.…”

Section: Other Phosphorus Containing Superbases: Verkades Proazaphospmentioning

confidence: 98%

Physico‐Chemical Properties of Organosuperbases

Margetić

2009

Superbases for Organic Synthesis

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Section: Other Phosphorus Containing Superbases: Verkades Proazaphospmentioning

confidence: 98%

Physico‐Chemical Properties of Organosuperbases

Margetić

2009

Superbases for Organic Synthesis

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Sehr starke Organosuperbasen durch Verknüpfung von Imidazol‐ und Guanidinbasen – Synthese, Struktur und Basizität

Vazdar¹,

Kunetskiy²,

Saame³

et al. 2013

Angewandte Chemie

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Neue Strukturmotive für Organosuperbasen, die leicht zugänglich sind und hohe Basizitäten aufweisen, sind für viele Bereiche der Chemie dringend notwendig. Wir berichten hier über die Synthese von N,N′‐Bis(imidazolyl)guanidin‐Basen (BIG‐Basen). Ihre pKα‐Werte wurden zu 26.1–29.3 in THF bestimmt. Sie sind damit wahrscheinlich die stärksten phosphorfreien organischen Basen sowohl in Lösung als auch in der Gasphase. Rechnungen halfen bei der Bestimmung der strukturellen und elektronischen Faktoren, die zur beobachteten hohen Basizität beitragen.

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Very Strong Organosuperbases Formed by Combining Imidazole and Guanidine Bases: Synthesis, Structure, and Basicity

et al. 2013

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New structural motives for organosuperbases, that are easy to prepare and highly basic are urgently required in many areas of chemistry. The synthesis of N,N'-bis(imidazolyl)guanidine bases (BIG bases) is reported. Their pKα values are determined as 26.1-29.3 in THF. They are thus probably the strongest known phosphorous-free organic bases both in solution and in the gas phase. Calculations help to determine the structural and electronic factors giving rise to the high basicity.

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P[N(iBu)CH2CH2]3N: A versatile non-ionic base for the synthesis of higher coordinate silicates

Cited by 10 publications

References 31 publications

Physico‐Chemical Properties of Organosuperbases

Physico‐Chemical Properties of Organosuperbases

Sehr starke Organosuperbasen durch Verknüpfung von Imidazol‐ und Guanidinbasen – Synthese, Struktur und Basizität

Very Strong Organosuperbases Formed by Combining Imidazole and Guanidine Bases: Synthesis, Structure, and Basicity

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