Abstract:
The crystal structures of (+)-3, (±)-4 and P-(–)-5 were studied; the competitive H-bonding of carboxylic groups in (+)-3 and (±)-4 leads to disruption of crystal structure elements, used previously in crystal engineering of chiral bis(lactams); the new structure elements may be described as 1D homochiral R22(10) tapes; the diastereomeric resolution in P-(–)-5 is rationalised using an analogy between the H-bonded structure of the salt and 2,5-diaza-3,6-dioxobicyclo[2.2.2]octane-1,4-dicarboxylic acid dihydrate.
Document Type:
Article
Language: English
Citation:
D. A. Lenev, K. A. Lyssenko, R. G. Kostyanovsky, “Crystal engineering strategies in alkane-bis(ammonium) 2,5-diaza-3,6-dioxobicyclo[2.2.2]octane-1,4-dicarboxylates”, Mendeleev Commun., 14:6 (2004), 312–314
Linking options:
https://www.mathnet.ru/eng/mendc3924
https://www.mathnet.ru/eng/mendc/v14/i6/p312
This publication is cited in the following 6 articles:
Sirinan Kulchat, Jean‐Marie Lehn, “Dynamic Covalent Chemistry of Nucleophilic Substitution Component Exchange of Quaternary Ammonium Salts”, Chemistry — An Asian Journal, 10:11 (2015), 2484
Eugene A. Mash, “Crystal engineering with 1,4-piperazine-2,5-diones”, CrystEngComm, 16:37 (2014), 8620
Kirk E. Wells, Robin A. Weatherhead, Francis N. Murigi, Gary S. Nichol, Michael D. Carducci, Hugh D. Selby, Eugene A. Mash, “Organic Crystal Engineering with 1,4-Piperazine-2,5-diones. 8. Synthesis, Crystal Packing, and Thermochemistry of Piperazinediones Derived from 2-Amino-4,7-dialkoxyindan-2-carboxylic Acids”, Crystal Growth & Design, 12:10 (2012), 5056
Nathan W. Polaske, Gary S. Nichol, Lajos Z. Szabó, Bogdan Olenyuk, “Molecular Solids from Symmetrical Bis(piperazine-2,5-diones) with Open- and Closed-Monomer Conformations”, Crystal Growth & Design, 9:5 (2009), 2191
R. G. Kostyanovsky, K. A. Lyssenko, O. N. Krutius, V. R. Kostyanovsky, “Isomorphism of chiral ammonium salts Ph(All)N+Et(Me)X–·CHCl3”, Mendeleev Commun., 19:1 (2009), 19–20
Deogratias Ntirampebura, Bhumasamudram Jagadish, Gary S. Nichol, Michael D. Carducci, Alice Dawson, Asha Rajapakshe, Allen G. Oliver, William Clegg, Ross W. Harrington, Larry Layne, Jason I. Margolis, Eugene A. Mash, “Organic Crystal Engineering with 1,4-Piperazine-2,5-diones. 7. Crystal Packing of Piperazinediones Derived from 2-Amino-7-nitro-4-methoxyindan-2-carboxylic Acid”, Crystal Growth & Design, 8:9 (2008), 3257
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