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Spectroscopic (FT‐IR, FT‐Raman, UV, 1 H, and 13 C NMR) and theoretical studies of m ‐anisic acid and lithium, sodium, potassium, rubidium, and caesium m ‐anisates
Author(s) -
Kalinowska M.,
Świsłocka R.,
Rzączyńska Z.,
Sienkiewicz J.,
Lewandowski W.
Publication year - 2010
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.1581
Subject(s) - chemistry , rubidium , chemical shift , alkali metal , nmr spectra database , raman spectroscopy , lithium (medication) , inorganic chemistry , potassium , analytical chemistry (journal) , spectral line , organic chemistry , medicine , physics , astronomy , optics , endocrinology
Abstract In order to understand the nature of the interactions of biologically important ligands, it is necessary to carry out the physico‐chemical studies of these compounds with their biological targets (e.g., receptors in the cell or important cell components). Results of this study make it possible to predict some properties of a molecule, such as its reactivity, durability of complex compounds, and kinship to enzymes. In this paper the effect of alkali metal cations (Li, Na, K, Rb, and Cs) on the electronic structure of m ‐methoxybenzoic acid ( m ‐anisic acid) was studied. The experimental IR (in solid state and solution), Raman, UV (in solid state and solution), 1 H, and 13 C NMR spectra of m ‐methoxybenzoic acid, and its salts were registered, assigned, and analyzed. Some of the obtained results were compared with published data for o ‐anisic acid and o ‐anisates. The structures of anisic acid and Li, Na, and K m ‐anisates were optimized at the B3LYP/6‐311++G** level. The IR, 1 H, and 13 C NMR spectra and NPA, ChelpG, and MK atomic charges were calculated. The change of metal along with the series: Li → Na → K → Rb → Cs caused: (1) the change in the electronic charge distribution in anisate anion that is seen via the occurrence of the systematic shifts of several bands in the experimental and theoretical IR and Raman spectra of anisates; (2) systematic 1 H and 13 C NMR chemical shifts; (3) hypsochromic shifts in UV spectra of salts as compared to ligands. Copyright © 2009 John Wiley & Sons, Ltd.