Mechanochemical reaction of ninhydrin with aromatics, enols and amines: Synthesis, crystal structure and supramolecular self-assembly of cyclic and acyclic adducts
Ninhydrin and related indanone scaffolds are employed as effective synthon in organic and bioorganic chemistry. In the present work, the reactivity of ninhydrin is exploited to synthesize various cyclic and acyclic compounds using mortar and pestle grinding method. The reaction of ninhydrin with var...
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| Format: | Article |
| Language: | English |
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Elsevier
2023-01-01
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| Series: | Results in Chemistry |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2211715622004325 |
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| author | Suven Das Purak Das Suvendu Maity Prasanta Ghosh Arpita Dutta |
| author_facet | Suven Das Purak Das Suvendu Maity Prasanta Ghosh Arpita Dutta |
| author_sort | Suven Das |
| collection | DOAJ |
| description | Ninhydrin and related indanone scaffolds are employed as effective synthon in organic and bioorganic chemistry. In the present work, the reactivity of ninhydrin is exploited to synthesize various cyclic and acyclic compounds using mortar and pestle grinding method. The reaction of ninhydrin with various naphthols, phenols, acetylacetone/ethylacetoacetate under grinding condition led to fused/spirocyclic products. On the other hand, 2-methoxynaphthalene, 4-hydroxycoumarin, 1,3-indanedione, indole reacted with ninhydrin to afford simple C-2 arylated acyclic adducts. Single crystal X-ray diffraction study revealed that, ninhydrin-o-cresol adduct, which preferentially remains in the cyclic hemiketal form 6, self-assembled to adopt zipper architecture. However, ninhydrin-2-methoxynaphthalene adduct 7 was found to display corrugated sheet like arrangement. Scanning electron microscopy (SEM) study reveals that cyclic adducts 6, 8, 10 exhibit fibrillar morphology, whereas acyclic adducts 7, 12, 15 disclose sheet morphology. |
| first_indexed | 2024-03-13T04:14:08Z |
| format | Article |
| id | doaj.art-fa26bb7725be408a9bfff1c381c9f9d4 |
| institution | Directory Open Access Journal |
| issn | 2211-7156 |
| language | English |
| last_indexed | 2024-03-13T04:14:08Z |
| publishDate | 2023-01-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Results in Chemistry |
| spelling | doaj.art-fa26bb7725be408a9bfff1c381c9f9d42023-06-21T06:51:42ZengElsevierResults in Chemistry2211-71562023-01-015100713Mechanochemical reaction of ninhydrin with aromatics, enols and amines: Synthesis, crystal structure and supramolecular self-assembly of cyclic and acyclic adductsSuven Das0Purak Das1Suvendu Maity2Prasanta Ghosh3Arpita Dutta4Department of Chemistry, Rishi Bankim Chandra College for Women, Naihati, 24-Parganas (N), Pin-743165, India; Corresponding author.Department of Chemistry, Rishi Bankim Chandra College for Women, Naihati, 24-Parganas (N), Pin-743165, IndiaDepartment of Chemistry, R K Mission Residential College, Narendrapur, Kolkata 103, IndiaDepartment of Chemistry, R K Mission Residential College, Narendrapur, Kolkata 103, IndiaDepartment of Chemistry, Rishi Bankim Chandra Evening College, Naihati, 24-Parganas (N), Pin-743165, IndiaNinhydrin and related indanone scaffolds are employed as effective synthon in organic and bioorganic chemistry. In the present work, the reactivity of ninhydrin is exploited to synthesize various cyclic and acyclic compounds using mortar and pestle grinding method. The reaction of ninhydrin with various naphthols, phenols, acetylacetone/ethylacetoacetate under grinding condition led to fused/spirocyclic products. On the other hand, 2-methoxynaphthalene, 4-hydroxycoumarin, 1,3-indanedione, indole reacted with ninhydrin to afford simple C-2 arylated acyclic adducts. Single crystal X-ray diffraction study revealed that, ninhydrin-o-cresol adduct, which preferentially remains in the cyclic hemiketal form 6, self-assembled to adopt zipper architecture. However, ninhydrin-2-methoxynaphthalene adduct 7 was found to display corrugated sheet like arrangement. Scanning electron microscopy (SEM) study reveals that cyclic adducts 6, 8, 10 exhibit fibrillar morphology, whereas acyclic adducts 7, 12, 15 disclose sheet morphology.http://www.sciencedirect.com/science/article/pii/S2211715622004325NinhydrinMechanochemistryCyclic hemiketalX-ray crystal structureSEM study |
| spellingShingle | Suven Das Purak Das Suvendu Maity Prasanta Ghosh Arpita Dutta Mechanochemical reaction of ninhydrin with aromatics, enols and amines: Synthesis, crystal structure and supramolecular self-assembly of cyclic and acyclic adducts Results in Chemistry Ninhydrin Mechanochemistry Cyclic hemiketal X-ray crystal structure SEM study |
| title | Mechanochemical reaction of ninhydrin with aromatics, enols and amines: Synthesis, crystal structure and supramolecular self-assembly of cyclic and acyclic adducts |
| title_full | Mechanochemical reaction of ninhydrin with aromatics, enols and amines: Synthesis, crystal structure and supramolecular self-assembly of cyclic and acyclic adducts |
| title_fullStr | Mechanochemical reaction of ninhydrin with aromatics, enols and amines: Synthesis, crystal structure and supramolecular self-assembly of cyclic and acyclic adducts |
| title_full_unstemmed | Mechanochemical reaction of ninhydrin with aromatics, enols and amines: Synthesis, crystal structure and supramolecular self-assembly of cyclic and acyclic adducts |
| title_short | Mechanochemical reaction of ninhydrin with aromatics, enols and amines: Synthesis, crystal structure and supramolecular self-assembly of cyclic and acyclic adducts |
| title_sort | mechanochemical reaction of ninhydrin with aromatics enols and amines synthesis crystal structure and supramolecular self assembly of cyclic and acyclic adducts |
| topic | Ninhydrin Mechanochemistry Cyclic hemiketal X-ray crystal structure SEM study |
| url | http://www.sciencedirect.com/science/article/pii/S2211715622004325 |
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