J. Phys. Chem. A 2017, 121, 5665−5674

DOI: 10.1021/acs.jpca.7b05220

The Curious Case of 2‑Propyl‑1H‑benzimidazole in the Solid State: An Experimental and Theoretical Study

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.

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