Role of the C(2)-H Hydrogen Bond Donor in Gas-Phase Microsolvation of Imidazole Derivatives with ROH (R = CH3 , C2 H5 )
Abstract
Although the hydrogen-bonding properties of the protic solvents are comparable, a comparison of the gas-phase structures of water with those of the alcohols reveals certain similarities as well as differences. In this work we report the microsolvated clusters of imidazole derivatives, Benzimidazole (BIM) and N-methylbenzimidazole (MBIM) by methanol (M) and ethanol (E) in supersonic jet using electronic and vibrational spectroscopy and compare them with their hydrated clusters. The cluster sizes up to 1:2 of BIM/MBIM with methanol and ethanol, and up to 1:3 in the case of MBIM-methanol were observed. Both the N-H···O and O-H···N bound structures were observed for the BIM-M1 and BIM-E1 complexes. The O-H···N bound structures of 1:1 complexes of MBIM were relatively more stable than their BIM counterparts by about ∼0.25 kcal mol-1. Three distinct conformations (anti, gauche, and gauche') were identified for the O-H···N bound complexes of BIM-E1 and MBIM-E1. IR spectroscopy of the doubly and triply solvated clusters (namely BIM-M2, MBIM-M2,3 and MBIM-E2) gives unequivocal proof of H-bonded bridges that originate from the N acceptor and terminate at the C(2)-H group, similar to the analogous water clusters. These studies confirm tha...Continue Reading
References
C-H···Y hydrogen bonds in the complexes of p-cresol and p-cyanophenol with fluoroform and chloroform
Water bridges anchored by a C-HO hydrogen bond: the role of weak interactions in molecular solvation
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