Synthesis and Characterization of Quaternary Ammonium Salts Containing Carbonyl Functionality

This study is mainly focused on the synthesis of quaternary ammonium salts (QASs) derived from long-chain ketones as starting materials. The procedure used in this study is an extension of a new procedure for the preparation of iodinated acetone successfully developed in our lab and shown to be a ge...

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Main Author:	Salim, Norazlinaliza
Format:	Thesis
Language:	English English
Published:	2007
Subjects:	Quaternary ammonium salts - Synthesis Carbonyl compounds
Online Access:	http://psasir.upm.edu.my/id/eprint/5031/1/FS_2007_35.pdf
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id	my-upm-ir.5031
record_format	uketd_dc
spelling	my-upm-ir.50312013-05-27T07:19:54Z Synthesis and Characterization of Quaternary Ammonium Salts Containing Carbonyl Functionality 2007 Salim, Norazlinaliza This study is mainly focused on the synthesis of quaternary ammonium salts (QASs) derived from long-chain ketones as starting materials. The procedure used in this study is an extension of a new procedure for the preparation of iodinated acetone successfully developed in our lab and shown to be a generalized procedure for the preparation of iodinated ketones (Wong (2002), Badri (2000)), used to produce a class of quaternary amines containing a carbonyl functionality. Eight new QASs were produced; N-acetonyl-3-methylpyridinium iodide (17), N-acetonyl-4-methylpyridinium iodide (18), N-(2-oxoheptan-3-yl)pyridinium iodide (19), 2-methyl-N-(2-oxoheptan-3-yl)pyridinium iodide (20), N-2-oxoundecanylpyridinium iodide (21), 3-methyl-N-(2-oxoundeca-3-yl)pyridinium iodide (22), N-(2-oxododecyl)pyridinium iodide (23) and N-acetonyltrioctylammonium iodide (24). These compounds were characterized by FT-IR, 1H and 13C NMR and CHN elemental analysis. Single crystal x-ray analysis was used to solve the structures of 17 and 18. The crystal systems for both compounds were monoclinic. In the surface tension study, it was found that all of the QASs prepared lower the surface tension of water. The critical micelles concentration (CMC) value for the compound 24 (0.0339 mM) is the lowest of all the quaternary ammonium compounds prepared. Qualitative and quantitative antimicrobial assays showed that not all of the QASs prepared were active against bacteria and fungi tested. Only some of them were found to be active against the microorganisms. The compound 23 was strongly active (diameter>15 mm) against Salmonella choleraessuis and Bacillus subtilis wild type with 20 mm and 25 mm diameter inhibition zones, respectively. There are higher than the control, Streptomycin (17 mm and 15 mm respectively). The presence of long-chain ketones moderately increases the inhibiting effect against the selected microorganisms. The MIC value for the compound 23 against Salmonella choleraessuis is 12500 μg ml-1. The MIC value for the compound 23 (1560 μg ml-1) against Bacillus subtilis is higher than the control, Streptomycin (48.8 μg ml-1). Quaternary ammonium salts - Synthesis Carbonyl compounds 2007 Thesis http://psasir.upm.edu.my/id/eprint/5031/ http://psasir.upm.edu.my/id/eprint/5031/1/FS_2007_35.pdf application/pdf en public masters Universiti Putra Malaysia Quaternary ammonium salts - Synthesis Carbonyl compounds Science English
institution	Universiti Putra Malaysia
collection	PSAS Institutional Repository
language	English English
topic	Quaternary ammonium salts - Synthesis Carbonyl compounds
spellingShingle	Quaternary ammonium salts - Synthesis Carbonyl compounds Salim, Norazlinaliza Synthesis and Characterization of Quaternary Ammonium Salts Containing Carbonyl Functionality
description	This study is mainly focused on the synthesis of quaternary ammonium salts (QASs) derived from long-chain ketones as starting materials. The procedure used in this study is an extension of a new procedure for the preparation of iodinated acetone successfully developed in our lab and shown to be a generalized procedure for the preparation of iodinated ketones (Wong (2002), Badri (2000)), used to produce a class of quaternary amines containing a carbonyl functionality. Eight new QASs were produced; N-acetonyl-3-methylpyridinium iodide (17), N-acetonyl-4-methylpyridinium iodide (18), N-(2-oxoheptan-3-yl)pyridinium iodide (19), 2-methyl-N-(2-oxoheptan-3-yl)pyridinium iodide (20), N-2-oxoundecanylpyridinium iodide (21), 3-methyl-N-(2-oxoundeca-3-yl)pyridinium iodide (22), N-(2-oxododecyl)pyridinium iodide (23) and N-acetonyltrioctylammonium iodide (24). These compounds were characterized by FT-IR, 1H and 13C NMR and CHN elemental analysis. Single crystal x-ray analysis was used to solve the structures of 17 and 18. The crystal systems for both compounds were monoclinic. In the surface tension study, it was found that all of the QASs prepared lower the surface tension of water. The critical micelles concentration (CMC) value for the compound 24 (0.0339 mM) is the lowest of all the quaternary ammonium compounds prepared. Qualitative and quantitative antimicrobial assays showed that not all of the QASs prepared were active against bacteria and fungi tested. Only some of them were found to be active against the microorganisms. The compound 23 was strongly active (diameter>15 mm) against Salmonella choleraessuis and Bacillus subtilis wild type with 20 mm and 25 mm diameter inhibition zones, respectively. There are higher than the control, Streptomycin (17 mm and 15 mm respectively). The presence of long-chain ketones moderately increases the inhibiting effect against the selected microorganisms. The MIC value for the compound 23 against Salmonella choleraessuis is 12500 μg ml-1. The MIC value for the compound 23 (1560 μg ml-1) against Bacillus subtilis is higher than the control, Streptomycin (48.8 μg ml-1).
format	Thesis
qualification_level	Master's degree
author	Salim, Norazlinaliza
author_facet	Salim, Norazlinaliza
author_sort	Salim, Norazlinaliza
title	Synthesis and Characterization of Quaternary Ammonium Salts Containing Carbonyl Functionality
title_short	Synthesis and Characterization of Quaternary Ammonium Salts Containing Carbonyl Functionality
title_full	Synthesis and Characterization of Quaternary Ammonium Salts Containing Carbonyl Functionality
title_fullStr	Synthesis and Characterization of Quaternary Ammonium Salts Containing Carbonyl Functionality
title_full_unstemmed	Synthesis and Characterization of Quaternary Ammonium Salts Containing Carbonyl Functionality
title_sort	synthesis and characterization of quaternary ammonium salts containing carbonyl functionality
granting_institution	Universiti Putra Malaysia
granting_department	Science
publishDate	2007
url	http://psasir.upm.edu.my/id/eprint/5031/1/FS_2007_35.pdf
_version_	1747810335399608320

Synthesis and Characterization of Quaternary Ammonium Salts Containing Carbonyl Functionality

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