The Curious Case of 2-Propyl-1H-benzimidazole in the Solid State: An Experimental and Theoretical Study
María Mar Quesada-Moreno, Aurora J. Cruz-Cabeza, Juan Ramón Avilés-Moreno, Pilar Cabildo, Rosa M. Claramunt, Ibon Alkorta, José Elguero⊥, Francisco J. Zúñiga*#, and Juan Jesús López-González*†
The Journal of Physical Chemistry A
2-Propyl-1H-benzimidazole (2PrBzIm) is a small molecule, commercially available, which displays a curious behavior in the solid state. 2PrBzIm, although devoid of chirality by fast rotation about a single bond of the propyl group in solution, crystallizes as a conglomerate showing chiroptical properties. An exhaustive analysis of its crystal structure and a wide range of experiments monitored by vibrational circular dichroism spectroscopy eliminated all possibilities of an artifact. What remains is a new example of the unexplained phenomenon of persistent supramolecular chirality.
Vibrational circular dichroism, 2-Propyl-1H-benzimidazole, Solid State