Journal article
N-H···S Interaction Continues To Be an Enigma: Experimental and Computational Investigations of Hydrogen-Bonded Complexes of Benzimidazole with Thioethers
The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment, & general theory, Vol.122(17), pp.4313-4321
05/03/2018
DOI: 10.1021/acs.jpca.8b01943
PMID: 29641887
Abstract
The N-H···S hydrogen bond, even though classified as an unconventional hydrogen bond, is found to bear important structural implications on protein structure and folding. In this article, we report a gas-phase study of the N-H···S hydrogen bond between the model compounds of histidine (benzimidazole, denoted BIM) and methionine (dimethyl sulfide, diethyl sulfide, and tetrahydrothiophene, denoted Me
S, Et
S, and THT, respectively). A combination of laser spectroscopic methods such as laser-induced fluorescence (LIF), two-color resonant two-photon ionization (2cR2PI), and fluorescence depletion by infrared spectroscopy (FDIR) is used in conjunction with DFT and ab initio calculations to characterize the nature of this prevalent H-bonding interaction in simple bimolecular complexes. A single conformer was found to exist for the BIM-Me
S complex, whereas the BIM-Et
S and BIM-THT complexes showed the presence of three and two conformers, respectively. These conformers were characterized on the basis of IR spectroscopic results and electronic structure calculations. Quantum theory of atoms in molecules (QTAIM), natural bond orbital (NBO), and energy decomposition (NEDA) analyses were performed to investigate the nature of the N-H···S H-bond. Comparison of the results with the N-H···O type of interactions in BIM and indole revealed that the strength of the N-H···S H-bond is similar to N-H···O in these binary gas-phase complexes.
Details
- Title: Subtitle
- N-H···S Interaction Continues To Be an Enigma: Experimental and Computational Investigations of Hydrogen-Bonded Complexes of Benzimidazole with Thioethers
- Creators
- Sanjay Wategaonkar - Department of Chemical Sciences , Tata Institute of Fundamental Research , Homi Bhabha Road , Mumbai 400 005 , IndiaAditi Bhattacherjee - Department of Chemical Sciences , Tata Institute of Fundamental Research , Homi Bhabha Road , Mumbai 400 005 , India
- Resource Type
- Journal article
- Publication Details
- The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment, & general theory, Vol.122(17), pp.4313-4321
- DOI
- 10.1021/acs.jpca.8b01943
- PMID
- 29641887
- ISSN
- 1089-5639
- eISSN
- 1520-5215
- Grant note
- DOI: 10.13039/501100001405, name: Tata Institute of Fundamental Research
- Language
- English
- Date published
- 05/03/2018
- Academic Unit
- Chemistry
- Record Identifier
- 9984216710902771
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