1. Imidazolium 1,3-Benzazaphospholide Ion Pairs with Strong C-H···N Hydrogen Bonds - Synthesis, Structures, and Reactivity.
- Author
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Pi, Chengfu, Yu, Xiaoling, and Zheng, Wenjun
- Subjects
IMIDAZOLES ,CHEMICAL synthesis ,HETEROCYCLIC compounds synthesis ,CYCLIC compounds synthesis ,HYDROGEN bonding ,MOLECULAR association - Abstract
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 (¹H,13 C{1H}, and31 P{¹H}) NMR and IR spectroscopy, and X-ray diffraction analysis. The structures feature ion pair conformation in the solid state with strong charge-assisted C-H···N or N-H···N interaction. [ABSTRACT FROM AUTHOR]- Published
- 2015
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