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Biomedical and Biopharmaceutical Research J o r n a l d e I n v e s t i g a ç ã o B i o m é d i c a e B i o f a r m a c ê u t i c a
Synthesis of benzoazole ionic liquids and evaluation of their antimicrobial activity
AbstractA new class of chemicals composed not of molecules but ions, an organic cation and an organic or inorganic anion, has recently attracted attention. When these new kind of salts are in the liquid state below 100 oC, they are named ionic liquids (ILs). In this work, the synthesis of ionic liquids obtained from a 2-mercaptobenzimidazole, 2-mercaptobenzoxazole or 2-mercaptobenzothiazole anion and 1-alkyl-3-methylimidazolium or choline cation are described. The antimicrobial activity against several Gram-positive and Gram-negative bacteria and a yeast was also evaluated.
Keywords: Ionic liquids, benzoazole, choline, antimicrobial activity
Resumo:Uma nova classe de compostos químicos constituídos não por moléculas mas por iões, um catião orgânico e um anião orgânico ou inorgânico, tem atraído recentemente muita atenção. Quando estes novos tipos de sais estão no estado líquido, abaixo de 100 °C, são chamados líquidos iónicos (LI). Neste trabalho, é descrita a síntese de líquidos iónicos obtidos a partir de 2-mercaptobenzimidazol, 2-mercaptobenzoxazol ou o anião 2-mercaptobenzotiazol e o catião 1-alquil-3-metilimidazólio ou o catião colina. A atividade antimicrobiana destes LI sobre várias bactérias Gram-positivas, Gram-negativas e uma levedura foi avaliada.
X‐ray diffraction structure of two new bis [1‐methyl‐3‐(methoxycarbonylmethyl) benzimidazolium]2+ [CuBr4]2− and [ZnBr4]2− compounds has been determined. Zn‐crystal is monoclinic with perfect Td symmetry of the ZnBr4 tetrahedron, whereas the Cu‐compound is orthorhombic with D2d symmetry of CuBr4 tetrahedron. The difference in these structures is described as due to the static Jahn‐Teller effect. Vibrational spectroscopy (1800–3200 cm−1) identified hydrogen bond network. NIR‐UV‐Vis spectra (5000–50000 cm−1) are dominated by ligand‐to‐metal bands with d‐d transition contribution. EPR results (Q‐band) analyzed in terms of the MO‐theory showed a very strong delocalization of unpaired electron density on ligands accompanied by the Cu(II) 4pz orbital contribution. This effect is partially compensated by charge transfer transitions to the EPR g‐factor.
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