Issue 16, 2016

Switching between cis and trans anions of 2-(2′-hydroxyphenyl)benzimidazole: a molecular rotation perturbed by chemical stabilization

Abstract

Despite the fact that 2-(2′-hydroxyphenyl)benzimidazole (HPBI) exists as the cis and trans enol in neutral form, it was reported to exist only in the trans form upon deprotonation in an aqueous medium. It was also shown that the dianion formed in the ground state can be re-protonated to form the trans-anion in the excited state. In the present study, the cis-anion and dianion could be obtained upon proper stabilization in suitable environments. Switching between the cis and trans-anion was demonstrated to be possible by changing the environment. Theoretical calculations were performed to substantiate the existence of the cis-anion and dianion. In contrast to a literature report, it was shown that the ‘OH’ group deprotonates before the ‘NH’ group to form a monoanion not only in protic solvents but also in aprotic solvents.

Graphical abstract: Switching between cis and trans anions of 2-(2′-hydroxyphenyl)benzimidazole: a molecular rotation perturbed by chemical stabilization

Supplementary files

Article information

Article type
Paper
Submitted
23 Dec 2015
Accepted
22 Mar 2016
First published
22 Mar 2016

Phys. Chem. Chem. Phys., 2016,18, 11081-11090

Switching between cis and trans anions of 2-(2′-hydroxyphenyl)benzimidazole: a molecular rotation perturbed by chemical stabilization

S. Sahu, M. Das and G. Krishnamoorthy, Phys. Chem. Chem. Phys., 2016, 18, 11081 DOI: 10.1039/C5CP07949G

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