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https://doi.org/10.5562/cca2476

Mechanochemical and Conformational Study of N-heterocyclic Carbonyl-Oxime Transformations

Ines Primožič   ORCID icon orcid.org/0000-0003-1154-4735 ; Department of Chemistry, Faculty of Science, University of Zagreb, Horvatovac 102a, HR-10000 Zagreb, Croatia
Tomica Hrenar ; Department of Chemistry, Faculty of Science, University of Zagreb, Horvatovac 102a, HR-10000 Zagreb, Croatia
Krešimir Baumann ; Department of Chemistry, Faculty of Science, University of Zagreb, Horvatovac 102a, HR-10000 Zagreb, Croatia
Lucija Krišto ; Department of Chemistry, Faculty of Science, University of Zagreb, Horvatovac 102a, HR-10000 Zagreb, Croatia
Ivana Križić ; Department of Chemistry, Faculty of Science, University of Zagreb, Horvatovac 102a, HR-10000 Zagreb, Croatia
Srđanka Tomić ; Department of Chemistry, Faculty of Science, University of Zagreb, Horvatovac 102a, HR-10000 Zagreb, Croatia

Puni tekst: engleski, pdf (3 MB) str. 153-160 preuzimanja: 709* citiraj
APA 6th Edition
Primožič, I., Hrenar, T., Baumann, K., Krišto, L., Križić, I. i Tomić, S. (2014). Mechanochemical and Conformational Study of N-heterocyclic Carbonyl-Oxime Transformations. Croatica Chemica Acta, 87 (2), 153-160. https://doi.org/10.5562/cca2476
MLA 8th Edition
Primožič, Ines, et al. "Mechanochemical and Conformational Study of N-heterocyclic Carbonyl-Oxime Transformations." Croatica Chemica Acta, vol. 87, br. 2, 2014, str. 153-160. https://doi.org/10.5562/cca2476. Citirano 14.11.2019.
Chicago 17th Edition
Primožič, Ines, Tomica Hrenar, Krešimir Baumann, Lucija Krišto, Ivana Križić i Srđanka Tomić. "Mechanochemical and Conformational Study of N-heterocyclic Carbonyl-Oxime Transformations." Croatica Chemica Acta 87, br. 2 (2014): 153-160. https://doi.org/10.5562/cca2476
Harvard
Primožič, I., et al. (2014). 'Mechanochemical and Conformational Study of N-heterocyclic Carbonyl-Oxime Transformations', Croatica Chemica Acta, 87(2), str. 153-160. https://doi.org/10.5562/cca2476
Vancouver
Primožič I, Hrenar T, Baumann K, Krišto L, Križić I, Tomić S. Mechanochemical and Conformational Study of N-heterocyclic Carbonyl-Oxime Transformations. Croatica Chemica Acta [Internet]. 2014 [pristupljeno 14.11.2019.];87(2):153-160. https://doi.org/10.5562/cca2476
IEEE
I. Primožič, T. Hrenar, K. Baumann, L. Krišto, I. Križić i S. Tomić, "Mechanochemical and Conformational Study of N-heterocyclic Carbonyl-Oxime Transformations", Croatica Chemica Acta, vol.87, br. 2, str. 153-160, 2014. [Online]. https://doi.org/10.5562/cca2476

Sažetak
New mechanochemical pathways for the transformation of six N-heterocyclic carbonyl compounds into oximes using hydroxylamine hydrochloride were explored. Reactions were performed first without any base since the heterocyclic moieties (imidazole, benzimidazole, pyridine and quinuclidine) have an intrinsic basic nitrogen atom. This green, solvent free method was suitable for all compounds (up to quantitative yields) except for N-benzyl substituted imidazole and benzimidazole-2-carbaldehyde. For the slower reacting aldehydes, reactions with liquid assisted grinding and addition of sodium hydroxide were performed as well. Conformational analysis and quantum-chemical calculations revealed steric and electronic reasons for the lower reactivity of N-benzyl substituted derivatives.

Ključne riječi
nitrogen heterocycles; oximes; mechanochemical synthesis; conformational analysis; DFT

Hrčak ID: 127914

URI
https://hrcak.srce.hr/127914

Posjeta: 950 *