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Mendeleev Communications, 2006, Volume 16, Issue 4, Pages 222–223
DOI: https://doi.org/10.1070/MC2006v016n04ABEH002195
(Mi mendc3596)
 

This article is cited in 20 scientific papers (total in 20 papers)

Pyramidal amide nitrogen in N-acyloxy-N-alkoxyureas and N-acyloxy-N-alkoxycarbamates

O. V. Shishkina, R. I. Zubatyuka, V. G. Shtamburgb, A. V. Tsygankovb, E. A. Klotsb, A. V. Mazepac, R. G. Kostyanovskyd

a STC 'Institute for Single Crystals', National Academy of Sciences of Ukraine, Kharkov, Ukraine
b Department of Chemistry, Dnepropetrovsk National University, Dnepropetrovsk, Ukraine
c A.V. Bogatsky Physico-Chemical Institute, National Academy of Sciences of Ukraine, Odessa, Ukraine
d N.N. Semenov Federal Research Center for Chemical Physics, Russian Academy of Sciences, Moscow, Russian Federation
Abstract: The XRD studies of N-acyloxy-N-alkoxyamides 1, 2 have revealed a highly pyramidal configuration of amide nitrogen in the O–N–O group
Document Type: Article
Language: English


Citation: O. V. Shishkin, R. I. Zubatyuk, V. G. Shtamburg, A. V. Tsygankov, E. A. Klots, A. V. Mazepa, R. G. Kostyanovsky, “Pyramidal amide nitrogen in N-acyloxy-N-alkoxyureas and N-acyloxy-N-alkoxycarbamates”, Mendeleev Commun., 16:4 (2006), 222–223
Linking options:
  • https://www.mathnet.ru/eng/mendc3596
  • https://www.mathnet.ru/eng/mendc/v16/i4/p222
  • This publication is cited in the following 20 articles:
    1. V.G. Shtamburg, E.A. Klots, V.V. Shtamburg, A.A. Anishchenko, S.V. Shishkina, S.V. Kravchenko, A.V. Mazepa, “Structure of N-acetoxy-N-benzyloxyurea”, Vopr. Khim. Khim. Tekhnol., 2024, no. 4, 88  crossref
    2. Vasiliy G. Shtamburg, Evgeniy A. Klots, Victor V. Shtamburg, Andrey A. Anishchenko, Svitlana V. Shishkina, Alexander V. Mazepa, “Nucleophilic substitution at nitrogen atom. N-Alkoxy-N-(dimethoxyphosphoryl)ureas, synthesis and structure”, Journal of Molecular Structure, 1277 (2023), 134865  crossref
    3. Stephen A. Glover, Adam A. Rosser, Amide Bond Activation, 2022, 29  crossref
    4. Stephen A. Glover, Rhiannon R. Schumacher, “Mutagenicity of N-acyloxy-N-alkoxyamides as an indicator of DNA intercalation: The role of fluorene and fluorenone substituents as DNA intercalators”, Mutation Research/Genetic Toxicology and Environmental Mutagenesis, 863-864 (2021), 503299  crossref
    5. Irina G. Tkachenko, Sergey A. Komykhov, Eugene S. Gladkov, Vladimir I. Musatov, Valentyn A. Chebanov, Sergey M. Desenko, “Acetic aldehyde in multicomponent synthesis of azolopyrimidine derivatives in water”, Chem Heterocycl Comp, 55:4-5 (2019), 392  crossref
    6. Stephen A. Glover, Adam A. Rosser, “Heteroatom Substitution at Amide Nitrogen—Resonance Reduction and HERON Reactions of Anomeric Amides”, Molecules, 23:11 (2018), 2834  crossref
    7. Stephen A. Glover, Adam A. Rosser, “The role of substituents in the HERON reaction of anomeric amides”, Can. J. Chem., 94:12 (2016), 1169  crossref
    8. V. G. Shtamburg, R. G. Kostyanovsky, A. V. Tsygankov, V. V. Shtamburg, O. V. Shishkin, R. I. Zubatyuk, A. V. Mazepa, S. V. Kravchenko, “Geminal systems”, Russ Chem Bull, 64:1 (2015), 62  crossref
    9. Stephen A. Glover, Adam A. Rosser, Avat (Arman) Taherpour, Ben W. Greatrex, “Formation and HERON Reactivity of Cyclic N,N-Dialkoxyamides”, Aust. J. Chem., 67:3 (2014), 507  crossref
    10. V. G. Shtamburg, O. V. Shishkin, V. V. Shtamburg, R. I. Zubatyuk, A. V. Mazepa, R. G. Kostyanovsky, “N-Alkoxy-N-chloroureas in the synthesis of 3,4-dihydro-1H-2,1-benzoxazine-1-carboxamide and 1-alkoxy-1,3-dihydrobenzimidazol-2-ones”, Chem Heterocycl Comp, 49:8 (2013), 1195  crossref
    11. S. Kubik, Knowledge Updates 2013/3, 2013  crossref
    12. V. G. Shtamburg, A. V. Tsygankov, O. V. Shishkin, R. I. Zubatyuk, V. V. Shtamburg, M. V. Gerasimenko, A. V. Mazepa, R. G. Kostyanovsky, “1-Alkoxyamino-4-dimethylaminopyridinium derivatives as new representatives of O–N–N+ geminal systems and their structure†”, Mendeleev Commun., 22:2 (2012), 92–94  mathnet  crossref
    13. V. G. Shtamburg, A. V. Tsygankov, O. V. Shishkin, R. I. Zubatyuk, B. V. Uspensky, V. V. Shtamburg, A. V. Mazepa, R. G. Kostyanovsky, “The properties and structure of N-chloro-N-methoxy-4-nitrobenzamide”, Mendeleev Commun., 22:3 (2012), 164–166  mathnet  crossref
    14. V. G. Shtamburg, A. V. Tsygankov, M. V. Gerasimenko, O. V. Shishkin, R. I. Zubatyuk, A. V. Mazepa, R. G. Kostyanovsky, “New approach to N,N-dialkoxy-N′-arylureas and N,N-dialkoxycarbamates”, Mendeleev Commun., 21:1 (2011), 50–52  mathnet  crossref
    15. Stephen A. Glover, Patai's Chemistry of Functional Groups, 2010  crossref
    16. Jennifer P. Johns, Arjan van Losenoord, Clément Mary, Pierre Garcia, Damian S. Pankhurst, Adam A. Rosser, Stephen A. Glover, “Thermal Decomposition of N-Acyloxy-N-alkoxyamides - a New HERON Reaction”, Aust. J. Chem., 63:12 (2010), 1717  crossref
    17. Oleg V. Shishkin, Vasiliy G. Shtamburg, Roman I. Zubatyuk, Dmitriy A. Olefir, Alexander V. Tsygankov, Alexander V. Prosyanik, Alexander V. Mazepa, Remir G. Kostyanovsky, “Chiral ureas with two electronegative substituents at 1‐N: An unusual case of coexisting pyramidal and almost planar 1‐N atoms in the same crystal”, Chirality, 21:7 (2009), 642  crossref
    18. Stephen A. Glover, Advances in Physical Organic Chemistry, 42, Advances in Physical Organic Chemistry Volume 42, 2007, 35  crossref
    19. V. G. Shtamburg, O. V. Shishkin, R. I. Zubatyuk, S. V. Kravchenko, A. V. Tsygankov, V. V. Shtamburg, V. B. Distanov, R. G. Kostyanovsky, “Synthesis, structure and properties of N-alkoxy-N-(1-pyridinium)urea salts, N-alkoxy-N-acyloxyureas and N,N-dialkoxyureas”, Mendeleev Commun., 17:3 (2007), 178–180  mathnet  crossref
    20. V. G. Shtamburg, O. V. Shishkin, R. I. Zubatyuk, S. V. Kravchenko, A. V. Tsygankov, A. V. Mazepa, E. A. Klots, R. G. Kostyanovsky, “N-Chloro-N-alkoxyureas: synthesis, structure and properties”, Mendeleev Commun., 16:6 (2006), 323–325  mathnet  crossref
    Citing articles in Google Scholar: Russian citations, English citations
    Related articles in Google Scholar: Russian articles, English articles
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