SYNTHESIS AND CONFORMATION OF p-(AMINO)BUTOXYCALIX[4]ARENE
Derivatization of 5,11,17,23-tetra-t-butyl-25,26,27,28-tetrahydroxycalix[4]-arene to 5,11,17,23-tetra-amino-25,26,27,28-tetrabutoxycalix[4]arene compound via etherification, ipso nitration, and reduction reactions, respectively has been conducted. The etherification reaction was carried out by reflu...
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| Format: | Article |
| Language: | English |
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Department of Chemistry, Universitas Gadjah Mada
2010-06-01
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| Series: | Indonesian Journal of Chemistry |
| Online Access: | https://jurnal.ugm.ac.id/ijc/article/view/21712 |
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| author | Firdaus Firdaus Jumina Jumina Hardjono Sastrohamidjojo |
| author_facet | Firdaus Firdaus Jumina Jumina Hardjono Sastrohamidjojo |
| author_sort | Firdaus Firdaus |
| collection | DOAJ |
| description | Derivatization of 5,11,17,23-tetra-t-butyl-25,26,27,28-tetrahydroxycalix[4]-arene to 5,11,17,23-tetra-amino-25,26,27,28-tetrabutoxycalix[4]arene compound via etherification, ipso nitration, and reduction reactions, respectively has been conducted. The etherification reaction was carried out by refluxed the mixture of 5,11,17,23-tetra-t-butyl-25,26,27,28-tetrahydroxy-calix[4]arene, 1-bromobutane, NaI, and NaH in solvent mixture of THF-DMF (10:1 v/v) and nitrogen atmosphere for 4 hours to resulted 5,11,17,23-tetra-t-butyl-25,26,27,28-tetrabutoxycalix[4]-arene 84% in yield; ipso nitration reaction was carried out by stirred the mixture of 5,11,17,23-tetra-t-butyl-25,26,27,28-tetrabutoxycalix[4]arene and HNO3 100% in solvent mixture of dichloromethane-acetic acid glacial (1:1 v/v) for 2 hours and than refluxed for 1 hour to resulted 5,11,17,23-tetra-nitro-25,26,27,28-tetra-butoxycalix[4]arene 50% in yield; and reduction reaction was carried out by refluxed the mixture of 5,11,17,23-tetra-nitro-25,26,27,28-tetrabutoxycalix[4]arene and SnCl2/HCl reductor in ethanol solvent for 6 hours to resulted 5,11,17,23-tetra-amino-25,26,27,28-tetrabutoxycalix[4]arene 67% in yield. In the etherification reaction, the conformation of calix[4]arene compound was converted from cone to partial cone; but in the followed reactions, i.e. nitration and reduction reactions, the conformation of calix[4]arene compounds were remain in partial cone.
Keywords: aminobutoxycalixarene, conformation, etherification, ipso nitration, reduction |
| first_indexed | 2024-12-17T22:15:38Z |
| format | Article |
| id | doaj.art-477cd73fa5cd45c0ba3603e0a11c0688 |
| institution | Directory Open Access Journal |
| issn | 1411-9420 2460-1578 |
| language | English |
| last_indexed | 2024-12-17T22:15:38Z |
| publishDate | 2010-06-01 |
| publisher | Department of Chemistry, Universitas Gadjah Mada |
| record_format | Article |
| series | Indonesian Journal of Chemistry |
| spelling | doaj.art-477cd73fa5cd45c0ba3603e0a11c06882022-12-21T21:30:37ZengDepartment of Chemistry, Universitas Gadjah MadaIndonesian Journal of Chemistry1411-94202460-15782010-06-0171495710.22146/ijc.2171214810SYNTHESIS AND CONFORMATION OF p-(AMINO)BUTOXYCALIX[4]ARENEFirdaus Firdaus0Jumina Jumina1Hardjono Sastrohamidjojo2Department of Chemistry, Faculty of Mathematics and Natural Sciences, Hasanuddin University, Jl. Perintis Kemerdekaan Km 10 Makassar Indonesia 90245Department of Chemistry, Faculty of Mathematics and Natural Sciences, Gadjah Mada University, Sekip Utara Yogyakarta Indonesia 55281Department of Chemistry, Faculty of Mathematics and Natural Sciences, Gadjah Mada University, Sekip Utara Yogyakarta Indonesia 55281Derivatization of 5,11,17,23-tetra-t-butyl-25,26,27,28-tetrahydroxycalix[4]-arene to 5,11,17,23-tetra-amino-25,26,27,28-tetrabutoxycalix[4]arene compound via etherification, ipso nitration, and reduction reactions, respectively has been conducted. The etherification reaction was carried out by refluxed the mixture of 5,11,17,23-tetra-t-butyl-25,26,27,28-tetrahydroxy-calix[4]arene, 1-bromobutane, NaI, and NaH in solvent mixture of THF-DMF (10:1 v/v) and nitrogen atmosphere for 4 hours to resulted 5,11,17,23-tetra-t-butyl-25,26,27,28-tetrabutoxycalix[4]-arene 84% in yield; ipso nitration reaction was carried out by stirred the mixture of 5,11,17,23-tetra-t-butyl-25,26,27,28-tetrabutoxycalix[4]arene and HNO3 100% in solvent mixture of dichloromethane-acetic acid glacial (1:1 v/v) for 2 hours and than refluxed for 1 hour to resulted 5,11,17,23-tetra-nitro-25,26,27,28-tetra-butoxycalix[4]arene 50% in yield; and reduction reaction was carried out by refluxed the mixture of 5,11,17,23-tetra-nitro-25,26,27,28-tetrabutoxycalix[4]arene and SnCl2/HCl reductor in ethanol solvent for 6 hours to resulted 5,11,17,23-tetra-amino-25,26,27,28-tetrabutoxycalix[4]arene 67% in yield. In the etherification reaction, the conformation of calix[4]arene compound was converted from cone to partial cone; but in the followed reactions, i.e. nitration and reduction reactions, the conformation of calix[4]arene compounds were remain in partial cone. Keywords: aminobutoxycalixarene, conformation, etherification, ipso nitration, reductionhttps://jurnal.ugm.ac.id/ijc/article/view/21712 |
| spellingShingle | Firdaus Firdaus Jumina Jumina Hardjono Sastrohamidjojo SYNTHESIS AND CONFORMATION OF p-(AMINO)BUTOXYCALIX[4]ARENE Indonesian Journal of Chemistry |
| title | SYNTHESIS AND CONFORMATION OF p-(AMINO)BUTOXYCALIX[4]ARENE |
| title_full | SYNTHESIS AND CONFORMATION OF p-(AMINO)BUTOXYCALIX[4]ARENE |
| title_fullStr | SYNTHESIS AND CONFORMATION OF p-(AMINO)BUTOXYCALIX[4]ARENE |
| title_full_unstemmed | SYNTHESIS AND CONFORMATION OF p-(AMINO)BUTOXYCALIX[4]ARENE |
| title_short | SYNTHESIS AND CONFORMATION OF p-(AMINO)BUTOXYCALIX[4]ARENE |
| title_sort | synthesis and conformation of p amino butoxycalix 4 arene |
| url | https://jurnal.ugm.ac.id/ijc/article/view/21712 |
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