Synthesis of Glucose Based Water Soluble Molecular Tweezers as Molecular Recognition Scaffolds
Dry heating of 4,4’-methylenedianiline and N,N’-dimethyl-4,4’-methylenedianiline with 5,6-anhydro-1,2-o-isopropylidene-α-D-glucofuranose afforded molecular tweezers having tertiary amino group linked to C-6 of the glucose moiety. These molecular tweezers on deprotection with dilute acid yielded wat...
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| Format: | Article |
| Language: | English |
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Wiley
2011-01-01
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| Series: | E-Journal of Chemistry |
| Online Access: | http://dx.doi.org/10.1155/2011/274236 |
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| author | Lalit Sharma |
| author_facet | Lalit Sharma |
| author_sort | Lalit Sharma |
| collection | DOAJ |
| description | Dry heating of 4,4’-methylenedianiline and N,N’-dimethyl-4,4’-methylenedianiline with 5,6-anhydro-1,2-o-isopropylidene-α-D-glucofuranose afforded molecular tweezers having tertiary amino group linked to C-6 of the glucose moiety. These molecular tweezers on deprotection with dilute acid yielded water soluble analogs which were explored for the solubilization of neutral arenes viz. naphthalene, biphenyl, durene, fluorene, anthracene and phenanthrene in acidic aqueous medium. These solid liquid extraction studies revealed that 6,6’-(N,N’-dimethyl-4’’,4’’’-methylenedianilino) bis (α-D-glucopyranose) causes an approximate 31 fold increase in the solubility of biphenyl in aqueous medium and has best complementarity for naphthalene by forming 1:1 complex. |
| format | Article |
| id | doaj-art-56d86b2356d646c28bb112a903faec4e |
| institution | OA Journals |
| issn | 0973-4945 2090-9810 |
| language | English |
| publishDate | 2011-01-01 |
| publisher | Wiley |
| record_format | Article |
| series | E-Journal of Chemistry |
| spelling | doaj-art-56d86b2356d646c28bb112a903faec4e2025-08-20T02:05:56ZengWileyE-Journal of Chemistry0973-49452090-98102011-01-018131932510.1155/2011/274236Synthesis of Glucose Based Water Soluble Molecular Tweezers as Molecular Recognition ScaffoldsLalit Sharma0Department of Applied ChemistryShaheed Bhagat Singh College of Engg & Tech., Ferozepur-52 004, IndiaDry heating of 4,4’-methylenedianiline and N,N’-dimethyl-4,4’-methylenedianiline with 5,6-anhydro-1,2-o-isopropylidene-α-D-glucofuranose afforded molecular tweezers having tertiary amino group linked to C-6 of the glucose moiety. These molecular tweezers on deprotection with dilute acid yielded water soluble analogs which were explored for the solubilization of neutral arenes viz. naphthalene, biphenyl, durene, fluorene, anthracene and phenanthrene in acidic aqueous medium. These solid liquid extraction studies revealed that 6,6’-(N,N’-dimethyl-4’’,4’’’-methylenedianilino) bis (α-D-glucopyranose) causes an approximate 31 fold increase in the solubility of biphenyl in aqueous medium and has best complementarity for naphthalene by forming 1:1 complex.http://dx.doi.org/10.1155/2011/274236 |
| spellingShingle | Lalit Sharma Synthesis of Glucose Based Water Soluble Molecular Tweezers as Molecular Recognition Scaffolds E-Journal of Chemistry |
| title | Synthesis of Glucose Based Water Soluble Molecular Tweezers as Molecular Recognition Scaffolds |
| title_full | Synthesis of Glucose Based Water Soluble Molecular Tweezers as Molecular Recognition Scaffolds |
| title_fullStr | Synthesis of Glucose Based Water Soluble Molecular Tweezers as Molecular Recognition Scaffolds |
| title_full_unstemmed | Synthesis of Glucose Based Water Soluble Molecular Tweezers as Molecular Recognition Scaffolds |
| title_short | Synthesis of Glucose Based Water Soluble Molecular Tweezers as Molecular Recognition Scaffolds |
| title_sort | synthesis of glucose based water soluble molecular tweezers as molecular recognition scaffolds |
| url | http://dx.doi.org/10.1155/2011/274236 |
| work_keys_str_mv | AT lalitsharma synthesisofglucosebasedwatersolublemoleculartweezersasmolecularrecognitionscaffolds |