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Pregled bibliografske jedinice broj: 687252

Design, Synthesis, and X-ray Structural Analyses of Diamantane Diammonium Salts: Guests for Cucurbit[n]uril (CB[n]) Hosts


Šekutor, Marina; Molčanov, Krešimir; Cao, Liping; Isaacs, Lyle; Glaser, Robert; Mlinarić-Majerski, Kata
Design, Synthesis, and X-ray Structural Analyses of Diamantane Diammonium Salts: Guests for Cucurbit[n]uril (CB[n]) Hosts // European journal of organic chemistry, (2014), 2; 2533-2542 doi:10.1002/ejoc.201301844 (međunarodna recenzija, članak, znanstveni)


Naslov
Design, Synthesis, and X-ray Structural Analyses of Diamantane Diammonium Salts: Guests for Cucurbit[n]uril (CB[n]) Hosts

Autori
Šekutor, Marina ; Molčanov, Krešimir ; Cao, Liping ; Isaacs, Lyle ; Glaser, Robert ; Mlinarić-Majerski, Kata

Izvornik
European journal of organic chemistry (1434-193X) (2014), 2; 2533-2542

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
Diamantane diamines; cucurbit[n]uril; CB[n]/diamine complexes; stereochemistry; X-ray crystallography

Sažetak
New bisprimary and bisquaternary diamantane-1, 6- and -4, 9-diammonium/diaminium salts were synthesized, and characterized by NMR spectroscopy and X-ray crystallography. The impetus for these syntheses were previously reported X-ray crystallographic investigations of adamantane mono- and bisquaternary ammonium ions [3, 5-diMeAda-1-NH3 or Ada-1, 3-di(NMe3)] complexed with cucurbit[n]uril (n = 7, 8). The crystal structures were analyzed with the goal to ascertain possible structural hypotheses for high binding affinity guests bound within various diameter pumpkin-shaped hosts. While Diam-4, 9-di(NMe3I) 5 could be readily prepared from the bisprimary precursor, the corresponding Diam-1, 6-di(NMe3I) 14 could not be obtained even under strong reaction conditions. Stereochemical analysis of this situation suggests very severe steric non-bonding cis-1, 3-diaxial type H…H interactions between the 'axial'-type NMe3 group and neighboring 'axial' proton neighbors. These same interactions are found in Ada-2, 6-di(NMe3I) analogues, but they are alleviated in this smaller polycyclic skeleton via tilting the axial C(methylene)—NMe3 bond away from its axial neighbors. However, similar structural relief for Diam-1, 6-di(NMe3I) is not possible, since the C(methine)—NMe3 bond therein is ligated to the diamondoid's rigid skeleton.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Projekt / tema
098-0982933-2911 - Kavezasti spojevi: ugradbene jedinice u molekularnim sustavima (Kata Majerski, )
098-1191344-2943 - Protein-ligand međudjelovanja na atomnoj razini (Marija Luić, )

Ustanove
Institut "Ruđer Bošković", Zagreb

Časopis indeksira:


  • Current Contents Connect (CCC)
  • Web of Science Core Collection (WoSCC)
    • Science Citation Index Expanded (SCI-EXP)
    • SCI-EXP, SSCI i/ili A&HCI
  • Scopus


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