0434917 - ÚOCHB 2015 RIV GB eng J - Journal Article
Tewari, A. K. - Srivastava, P. - Singh, V. P. - Singh, P. - Kumar, R. - Khanna, R. S. - Srivastava, Pa. - Gnanasekaran, Ramachandran - Hobza, Pavel
Selective induced polarization through electron transfer in acetone and pyrazole ester derivatives via C-H center dot center dot center dot O=C interaction.
New Journal of Chemistry. Roč. 38, č. 10 (2014), s. 4885-4892. ISSN 1144-0546. E-ISSN 1369-9261
R&D Projects: GA ČR GBP208/12/G016
Institutional support: RVO:61388963
Keywords : O hydrogen bonds * noncovalent interactions * pi interactions
Subject RIV: CF - Physical ; Theoretical Chemistry
Impact factor: 3.086, year: 2014 ; AIS: 0.623, rok: 2014
DOI: https://doi.org/10.1039/c4nj00679h

A set of organic compounds (pyrazole ester derivatives, viz. 5-[3-(substituted)-propoxy]-3-methyl-1-phenyl-1H-pyrazole-4-carboxylic acid methyl ester and 5-[2-(substituted)-ethoxy]-3-methyl-1-phenyl-1H-pyrazole-4-carboxylic acid methyl ester) was synthesized and their affinity and stability towards the acetone molecule were tested by NMR. Further, the host guest complex formed has been studied by cyclic voltammetric titration. Interestingly, the acetone molecule selectively bound to the methyl group of the pyrazole moiety and stabilized the system. These findings are also supported by quantum chemical calculations using the DFT/B-LYP/TZVPP method. Apart from hydrogen bonding, an important role in stabilizing the complex is also played by the C H center dot center dot center dot pi interaction governed by dispersion energy. The study proves that a methyl-substituted pyrazol ester can act as a receptor for acetone.
Permanent Link: http://hdl.handle.net/11104/0238983