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

Literature Information

Publication Date 2016-03-22
DOI 10.1039/C5CP07949G
Impact Factor 3.676
Authors

Saugata Sahu, Minati Das, G. Krishnamoorthy


View Original

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.

Related Literature

Catalyst-free facile synthesis of 2-substituted benzothiazoles

Siva S. Panda, Alexander A. Oliferenko

2013-08-09 Communication

DOI: 10.1039/C3GC41255E

Structural features of ionic liquids: consequences for material preparation and organic reactivity

Anthony F. Masters, Thomas Maschmeyer

2013-08-12 Critical Review

DOI: 10.1039/C3GC41313F

One-pot transformation of alkynes into alcohols and amines with formic acid

Jia Li, Chao Wang, Dong Xue, Yawen Wei

2013-08-02 Communication

DOI: 10.1039/C3GC41133H

An effective, cost-efficient extraction method of biomass from wet microalgae with a functional polymeric membrane

Gursong Yoo, Youngmin Yoo, Jong-Hee Kwon, Cornelius Darpito, Sanjiv K. Mishra, Kwanyong Pak

2013-10-02 Paper

DOI: 10.1039/C3GC41695J

Depolymerisation of condensed tannins in ethanol as a gateway to biosourced phenolic synthons

Chahinez Aouf, Eric Dubreucq, Hélène Fulcrand

2013-08-23 Paper

DOI: 10.1039/C3GC41281D

Life cycle assessment of surfactants: the case of an alkyl polyglucoside used as a self emulsifier in cosmetics

Jérôme Guilbot, Sébastien Kerverdo, Alain Milius, Rémi Escola, Fredrik Pomrehn

2013-10-04 Paper

DOI: 10.1039/C3GC41338A

Continuous flow nanocatalysis: reaction pathways in the conversion of levulinic acid to valuable chemicals

J. Angel Menéndez, Antonio A. Romero, Elena Serrano, Javier Garcia-Martinez, Rafael Luque

2013-07-31 Paper

DOI: 10.1039/C3GC41022F

A self-assembled Pd6L8 nanoball for Suzuki–Miyaura coupling reactions in both homogeneous and heterogeneous formats

Chao-Wei Zhao, Jian-Ping Ma, Qi-Kui Liu, Yang Yu, Peng Wang, Yan-An Li, Kui Wang, Yu-Bin Dong

2013-09-05 Communication

DOI: 10.1039/C3GC41154K

You might also like

155412-88-71-(3-Aminophenyl)-3-...
Compound Q&A

How should waste containing 1-(D-Ribofuranosyl)-1,4-dihydro-3-pyridinecarboxamide (CAS: 19132-12-8) be handled?

Waste containing 1-(D-Ribofuranosyl)-1,4-dihydro-3-pyridinecarboxamide (CAS: 191...

19132-12-81-(D-Ribofuranosyl)-...
Compound Q&A

What regulatory guidelines apply to 2-Methyl-2-propanyl 3-bromo-3-(hydroxymethyl)-1-azetidinecarboxylate (CAS: 2007919-81-3)?

2-Methyl-2-propanyl 3-bromo-3-(hydroxymethyl)-1-azetidinecarboxylate (CAS: 20079...

2007919-81-32-Methyl-2-propanyl ...
Compound Q&A

What is N-(4-Chloro-2-pyridinyl)acetamide (CAS: 245056-66-0)?

N-(4-Chloro-2-pyridinyl)acetamide (CAS: 245056-66-0) is a chemical compound with...

245056-66-0N-(4-Chloro-2-pyridi...
Compound Q&A

What is 5-Chloro-2-hydroxybenzoic acid (CAS: 321-14-2)?

5-Chloro-2-hydroxybenzoic acid, also known as 5-chlorosalicylic acid, is an arom...

321-14-25-Chloro-2-hydroxybe...
Compound Q&A

What precautions should be taken when handling 1,1-Dichloro-1-fluoroethane (CAS: 1717-00-6)?

When handling 1,1-Dichloro-1-fluoroethane (CAS: 1717-00-6), it is important to u...

1717-00-61,1-Dichloro-1-fluor...
Compound Q&A

What are the physical and chemical properties of Fmoc-(2S,3R)-3-phenylpyrrolidine-2-carboxylic acid (CAS: 281655-32-1)?

Fmoc-(2S,3R)-3-phenylpyrrolidine-2-carboxylic acid is a white crystalline solid ...

281655-32-1Fmoc-(2S,3R)-3-pheny...
Compound Q&A

What are the main uses of 4-Amino-5-bromo-2-pyridinecarboxylic acid (CAS: 1363381-01-4)?

4-Amino-5-bromo-2-pyridinecarboxylic acid is primarily used as a precursor in th...

1363381-01-44-Amino-5-bromo-2-py...
1007881-98-2(S)-tert-butyl 2-((2...
Compound Q&A

What precautions should be taken when handling 8-bromo-2,2-dimethyl-3,4-dihydro-2H-1,4-benzoxazin-3-one (CAS: 688363-73-7)?

When handling 8-bromo-2,2-dimethyl-3,4-dihydro-2H-1,4-benzoxazin-3-one, use prop...

688363-73-78-bromo-2,2-dimethyl...

Source Journal

Physical Chemistry Chemical Physics

Physical Chemistry Chemical Physics
CiteScore: 5.5
Self-citation Rate: 10.3%
Articles per Year: 3036

Physical Chemistry Chemical Physics (PCCP) is an international journal co-owned by 19 physical chemistry and physics societies from around the world. This journal publishes original, cutting-edge research in physical chemistry, chemical physics and biophysical chemistry. To be suitable for publication in PCCP, articles must include significant innovation and/or insight into physical chemistry; this is the most important criterion that reviewers and Editors will judge against when evaluating submissions. The journal has a broad scope and welcomes contributions spanning experiment, theory, computation and data science. Topical coverage includes spectroscopy, dynamics, kinetics, statistical mechanics, thermodynamics, electrochemistry, catalysis, surface science, quantum mechanics, quantum computing and machine learning. Interdisciplinary research areas such as polymers and soft matter, materials, nanoscience, energy, surfaces/interfaces, and biophysical chemistry are welcomed if they demonstrate significant innovation and/or insight into physical chemistry. Joined experimental/theoretical studies are particularly appreciated when complementary and based on up-to-date approaches.

Recommended Compounds

Recommended Suppliers

Disclaimer
This page provides academic journal information for reference and research purposes only. We are not affiliated with any journal publishers and do not handle publication submissions. For publication-related inquiries, please contact the respective journal publishers directly.
If you notice any inaccuracies in the information displayed, please contact us at support@chemtradehub.com. We will promptly review and address your concerns.