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Pregled bibliografske jedinice broj: 800974

Steric hindrance to the syntheses and stabilities of 1, 5- and 2, 6- naphthalene N-permethylated diammonium salts


Škalamera, Ðani; Cao, Liping; Isaacs, Lyle; Glaser, Robert; Mlinarić-Majerski, Kata
Steric hindrance to the syntheses and stabilities of 1, 5- and 2, 6- naphthalene N-permethylated diammonium salts // Tetrahedron, 72 (2016), 12; 1541-1546 doi:10.1016/j.tet.2016.02.002 (međunarodna recenzija, članak, znanstveni)


Naslov
Steric hindrance to the syntheses and stabilities of 1, 5- and 2, 6- naphthalene N-permethylated diammonium salts

Autori
Škalamera, Ðani ; Cao, Liping ; Isaacs, Lyle ; Glaser, Robert ; Mlinarić-Majerski, Kata

Izvornik
Tetrahedron (0040-4020) 72 (2016), 12; 1541-1546

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

Ključne riječi
Naphthalene diamines Quaternary aminium salts H/D-exchange Stereochemistry 1; 8-Type peri-strain

Sažetak
A series of naphthalene-1, 5- and 2, 6-diamines and their N-methyl derivatives were synthesized and characterized. 1H NMR spectroscopy showed that an aqueous solution of naphthalene-2, 6-di(NMe3I) (2) underwent considerable demethylation over a 24 h period after its initial preparation. Exchange of the iodide nucleophilic anion by the triflate non-nucleophilic counter-ion afforded a stable quaternary aminium salt. H/D α-position exchange in D2O solutions of naphthalene-2, 6-di(NH2MeCl) (3·HCl) and naphthalene-2, 6-di(NHMe2Cl) (4·HCl) with acidic +NH protons was observed, but not in those of naphthalene-2, 6-di(NMe3I) or triflate (2 or 5). Exhaustive per-N-methylation of naphthalene-1, 5-di(NMe2) (7) afforded only the mixed naphthalene-1-NMe3I-5-NHMe2I quaternary aminium-tertiary ammonium salt due to severe 1, 8-type peri-strain.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Projekt / tema
098-0982933-2911 - Kavezasti spojevi: ugradbene jedinice u molekularnim sustavima (Kata Majerski, )

Ustanove
Institut "Ruđer Bošković", Zagreb

Časopis indeksira:


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


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