Urotropine Isomer (1,4,6,10-Tetraazaadamantane): Synthesis, Structure, and Chemistry

Autor:	Vladimir A. Tartakovsky, Alexey Yu. Sukhorukov, Sema L. Ioffe, Artem N. Semakin, Yulia V. Nelyubina, Yulia A. Khomutova
Rok vydání:	2014
Předmět:	Electron pair Functional importance Atomic orbital chemistry Computational chemistry Organic Chemistry Structural isomer chemistry.chemical_element Hyperconjugation Nitrogen
Zdroj:	The Journal of Organic Chemistry. 79:6079-6086
ISSN:	1520-6904 0022-3263
DOI:	10.1021/jo5007703
Popis:	The first synthesis of 1,4,6,10-tetraazaadamantane, the C3v-symmetrical structural isomer of urotropine (1,3,5,7-tetraazaadamantane), and a series of its derivatives is reported. X-ray and quantum-chemical studies revealed remarkable distinctions in structures of urotropine and "isourotropine" cations, probably arising from different types of hyperconjugation between lone electron pairs of nitrogen atoms and σ*C-N orbitals in these heterocage systems. Since substitution at bridge and bridgehead nitrogen atoms can be easily introduced, 1,4,6,10-tetraazaadamantane may be considered as a new rigid multivalent (3 + 1) scaffold for the design of functional molecules and materials.
Databáze:	OpenAIRE
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