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- Publisher Website: 10.1021/jo962185r
- Scopus: eid_2-s2.0-0031559392
- PMID: 11543606
- WOS: WOS:A1997XP91100039
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Article: Glycolonitrile Oligomerization: Structure of Isolated Oxazolines, Potential Heterocycles on the Early Earth
Title | Glycolonitrile Oligomerization: Structure of Isolated Oxazolines, Potential Heterocycles on the Early Earth |
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Authors | |
Issue Date | 1997 |
Citation | Journal of Organic Chemistry, 1997, v. 62, n. 16, p. 5522-5525 How to Cite? |
Abstract | A study of glycolonitrile polymerization has led to the isolation and characterization of two 2,5-dihydro-4-aminooxazoles, 4 and 5. Previous reports have misassigned these structures as s-triazines or pyrimidines. X-ray diffraction analysis of crystals of 4 and an acetylated oxazole derivative of 5 (6) confirm the proposed structures. Ab initio computations are used to assess the relative thermodynamic stability of three trimer isomers (an s-triazine, an aminohydroxypyrimidine, and an aminooxazoline), and the results indicate that 4 is a novel kinetic product. Mechanistic considerations rationalize kinetic oxazole formation over the more customary triazine or pyrimidine trimers. |
Persistent Identifier | http://hdl.handle.net/10722/341460 |
ISSN | 2023 Impact Factor: 3.3 2023 SCImago Journal Rankings: 0.724 |
ISI Accession Number ID |
DC Field | Value | Language |
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dc.contributor.author | Arrhenius, Gustaf | - |
dc.contributor.author | Baldridge, Kim K. | - |
dc.contributor.author | Richards-Gross, Sarah | - |
dc.contributor.author | Siegel, Jay S. | - |
dc.date.accessioned | 2024-03-13T08:42:59Z | - |
dc.date.available | 2024-03-13T08:42:59Z | - |
dc.date.issued | 1997 | - |
dc.identifier.citation | Journal of Organic Chemistry, 1997, v. 62, n. 16, p. 5522-5525 | - |
dc.identifier.issn | 0022-3263 | - |
dc.identifier.uri | http://hdl.handle.net/10722/341460 | - |
dc.description.abstract | A study of glycolonitrile polymerization has led to the isolation and characterization of two 2,5-dihydro-4-aminooxazoles, 4 and 5. Previous reports have misassigned these structures as s-triazines or pyrimidines. X-ray diffraction analysis of crystals of 4 and an acetylated oxazole derivative of 5 (6) confirm the proposed structures. Ab initio computations are used to assess the relative thermodynamic stability of three trimer isomers (an s-triazine, an aminohydroxypyrimidine, and an aminooxazoline), and the results indicate that 4 is a novel kinetic product. Mechanistic considerations rationalize kinetic oxazole formation over the more customary triazine or pyrimidine trimers. | - |
dc.language | eng | - |
dc.relation.ispartof | Journal of Organic Chemistry | - |
dc.title | Glycolonitrile Oligomerization: Structure of Isolated Oxazolines, Potential Heterocycles on the Early Earth | - |
dc.type | Article | - |
dc.description.nature | link_to_subscribed_fulltext | - |
dc.identifier.doi | 10.1021/jo962185r | - |
dc.identifier.pmid | 11543606 | - |
dc.identifier.scopus | eid_2-s2.0-0031559392 | - |
dc.identifier.volume | 62 | - |
dc.identifier.issue | 16 | - |
dc.identifier.spage | 5522 | - |
dc.identifier.epage | 5525 | - |
dc.identifier.isi | WOS:A1997XP91100039 | - |