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Experimental and density functional theory investigation of imine formation using microwave irradiation

Four starting materials comprising of N-(4,6-dimethylpyridin-2-yl)-4-formylbenzamide 1, 4-amino-N-(4,6-dimethylpyridin-2- yl)benzamide 2, 4-amino-2-methylbenzoic acid 3 and 4-formylbenzoic acid 4 react in a pairwise manner through the condensation reaction to give four imine derivatives, Imine 5, 6...

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Main Authors: Nasir, Fatin Ilyani, Lee, Mark Wun Fui, Chong, Yan Yi, Kassim, Mohammad, Hasbullah, Siti Aishah, Philip, Douglas, Hassan, Nurul Izzaty
Format: Article
Language:English
Published: Faculty of Science and Technology, Universiti Kebangsaan Malaysia 2020
Online Access:http://psasir.upm.edu.my/id/eprint/88892/1/ABSTRACT.pdf
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spelling oai:psasir.upm.edu.my:88892 http://psasir.upm.edu.my/id/eprint/88892/ Experimental and density functional theory investigation of imine formation using microwave irradiation Nasir, Fatin Ilyani Lee, Mark Wun Fui Chong, Yan Yi Kassim, Mohammad Hasbullah, Siti Aishah Philip, Douglas Hassan, Nurul Izzaty Four starting materials comprising of N-(4,6-dimethylpyridin-2-yl)-4-formylbenzamide 1, 4-amino-N-(4,6-dimethylpyridin-2- yl)benzamide 2, 4-amino-2-methylbenzoic acid 3 and 4-formylbenzoic acid 4 react in a pairwise manner through the condensation reaction to give four imine derivatives, Imine 5, 6, 7 and 8. A simple method has been developed for the synthesis of these imine derivatives under microwave irradiation. In addition, these compounds were synthesised also by conventional heating procedures for comparison. All the compounds synthesised were characterised by melting point, infrared, mass spectrometry, 1H and 13C NMR spectroscopy. Comparison between conventional and microwave irradiation was done by comparing total reaction time and percentage yield. The results suggest that microwave-irradiation lead to higher yields within very short reaction times. Compounds 1 and 2 crystallised in the orthorhombic (P212121 space group) and monoclinic (P21/c space group) crystal systems, respectively. The nature of minimal replicator of imine 6 via autocatalytic reaction was calculated using density functional theory (DFT) with the combination of hybrid functional B3LYP and 6-311G(d,p) basis set. The reaction pathway facilitated with the addition of imine 6 or imine 5 equipped with complementary recognition sites of two carboxylic acids and two 4,6 dimethylamidopyridines were predicted to be thermodynamically favourable. Faculty of Science and Technology, Universiti Kebangsaan Malaysia 2020 Article PeerReviewed text en http://psasir.upm.edu.my/id/eprint/88892/1/ABSTRACT.pdf Nasir, Fatin Ilyani and Lee, Mark Wun Fui and Chong, Yan Yi and Kassim, Mohammad and Hasbullah, Siti Aishah and Philip, Douglas and Hassan, Nurul Izzaty (2020) Experimental and density functional theory investigation of imine formation using microwave irradiation. Malaysian Journal of Analytical Sciences, 24 (3). 422 - 435. ISSN 1394-2506 https://mjas.analis.com.my/mjas/
institution UPM IR
collection UPM IR
language English
description Four starting materials comprising of N-(4,6-dimethylpyridin-2-yl)-4-formylbenzamide 1, 4-amino-N-(4,6-dimethylpyridin-2- yl)benzamide 2, 4-amino-2-methylbenzoic acid 3 and 4-formylbenzoic acid 4 react in a pairwise manner through the condensation reaction to give four imine derivatives, Imine 5, 6, 7 and 8. A simple method has been developed for the synthesis of these imine derivatives under microwave irradiation. In addition, these compounds were synthesised also by conventional heating procedures for comparison. All the compounds synthesised were characterised by melting point, infrared, mass spectrometry, 1H and 13C NMR spectroscopy. Comparison between conventional and microwave irradiation was done by comparing total reaction time and percentage yield. The results suggest that microwave-irradiation lead to higher yields within very short reaction times. Compounds 1 and 2 crystallised in the orthorhombic (P212121 space group) and monoclinic (P21/c space group) crystal systems, respectively. The nature of minimal replicator of imine 6 via autocatalytic reaction was calculated using density functional theory (DFT) with the combination of hybrid functional B3LYP and 6-311G(d,p) basis set. The reaction pathway facilitated with the addition of imine 6 or imine 5 equipped with complementary recognition sites of two carboxylic acids and two 4,6 dimethylamidopyridines were predicted to be thermodynamically favourable.
format Article
author Nasir, Fatin Ilyani
Lee, Mark Wun Fui
Chong, Yan Yi
Kassim, Mohammad
Hasbullah, Siti Aishah
Philip, Douglas
Hassan, Nurul Izzaty
spellingShingle Nasir, Fatin Ilyani
Lee, Mark Wun Fui
Chong, Yan Yi
Kassim, Mohammad
Hasbullah, Siti Aishah
Philip, Douglas
Hassan, Nurul Izzaty
Experimental and density functional theory investigation of imine formation using microwave irradiation
author_facet Nasir, Fatin Ilyani
Lee, Mark Wun Fui
Chong, Yan Yi
Kassim, Mohammad
Hasbullah, Siti Aishah
Philip, Douglas
Hassan, Nurul Izzaty
author_sort Nasir, Fatin Ilyani
title Experimental and density functional theory investigation of imine formation using microwave irradiation
title_short Experimental and density functional theory investigation of imine formation using microwave irradiation
title_full Experimental and density functional theory investigation of imine formation using microwave irradiation
title_fullStr Experimental and density functional theory investigation of imine formation using microwave irradiation
title_full_unstemmed Experimental and density functional theory investigation of imine formation using microwave irradiation
title_sort experimental and density functional theory investigation of imine formation using microwave irradiation
publisher Faculty of Science and Technology, Universiti Kebangsaan Malaysia
publishDate 2020
url http://psasir.upm.edu.my/id/eprint/88892/1/ABSTRACT.pdf
_version_ 1819300291032383488
score 13.4562235

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