TY - JOUR
T1 - Bis(benzimidazolium)methane salts
T2 - A potential guest for dibenzo-24-crown-8 towards [2]pseudorotaxanes
AU - Ghosh, Sabari
AU - Schmiedekamp, Ann Marie
AU - Mukhopadhyay, Chhanda
PY - 2012/11/25
Y1 - 2012/11/25
N2 - We investigated the threading of bis(benzimidazolium) methane moieties with DB24C8 at 35°C (room temperature) and found a high degree of association. The presence of threaded complexes was determined by 1H NMR and also supported by high resolution mass spectrometry and B3LYP/6- 31G**++calculations. A 2D NMR study was done to elucidate the host-guest geometry and the molecular interactions present. The variable temperature NMR experiment was done over a temperature range of 243-323 K. The threading was stable and visible even at 323 K. Acid-base equilibrium established the reversibility of the process. DFT optimized structures establish that two H-bonded links are present between O 1⋯O 4′ and O 3⋯O 2′ across the dibenzo axis of the crown.
AB - We investigated the threading of bis(benzimidazolium) methane moieties with DB24C8 at 35°C (room temperature) and found a high degree of association. The presence of threaded complexes was determined by 1H NMR and also supported by high resolution mass spectrometry and B3LYP/6- 31G**++calculations. A 2D NMR study was done to elucidate the host-guest geometry and the molecular interactions present. The variable temperature NMR experiment was done over a temperature range of 243-323 K. The threading was stable and visible even at 323 K. Acid-base equilibrium established the reversibility of the process. DFT optimized structures establish that two H-bonded links are present between O 1⋯O 4′ and O 3⋯O 2′ across the dibenzo axis of the crown.
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U2 - 10.1016/j.tet.2012.08.080
DO - 10.1016/j.tet.2012.08.080
M3 - Article
AN - SCOPUS:84867508779
VL - 68
SP - 9826
EP - 9835
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 47
ER -