Journal
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
Volume -, Issue 10, Pages 1804-1810Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejic.201500058
Keywords
Synthesis design; 1,3-Benzazaphospholides; Carbenes; Hydrogen bonds; Structure elucidation
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Funding
- National Natural Science Foundation of China (NSFC) [21271057, 21272143]
- Zhejiang Provincial Natural Science Foundation of China [Y4110570]
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The treatment of 2-phenyl-1H-1,3-benzazaphosphole (H[2-ph-bp], 1) with free 1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene (IMes, 2) and 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene (SIMes, 3) afforded two imidazolium 1,3-benzazaphospholides, [1,3-bis(2,4,6-trimethylphenyl)imidazolium 2-phenyl-1,3-benzazaphospholide [(IMesH)(+)(2-ph-bp)(-), 4] and 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazolium 2-phenyl-1,3-benzazaphospholide [(SIMesH)(+)(2-ph-bp)(-), 5], which further reacted with carbodiimide to give 2-(N,N-diisopropylcarbamimidoyl)-1,3-bis(2,4,6-trimethylphenyl)imidazolium 2-phenyl-1,3-benzazaphospholide (6) and 2-(N,N-diisopropylcarbamimidoyl)-1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazolium 2-phenyl-1,3-benzazaphospholide (7), respectively. These compounds were characterized by multinuclear (H-1, C-13{H-1}, and P-31{H-1}) NMR and IR spectroscopy, and X-ray diffraction analysis. The structures feature ion pair conformation in the solid state with strong charge-assisted C-HN or N-HN interaction.
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