Synthesis and Basicity Studies of Quinolino[7,8‑h]quinoline Derivatives

Rowlands, Gareth J.; Severinsen, Rebecca J.; Buchanan, Jenna K.; Shaffer, Karl J.; Jameson, Heather T.; Thennakoon, Nishani; Leito, Ivo; Lõkov, Märt; Kütt, Agnes; Vianello, Robert; Despotović, Ines; Radić, Nena; Plieger, Paul G.

doi:10.1021/acs.joc.0c01428

Pregled bibliografske jedinice broj: 1099185

Synthesis and Basicity Studies of Quinolino[7,8‑h]quinoline Derivatives

Rowlands, Gareth J.; Severinsen, Rebecca J.; Buchanan, Jenna K.; Shaffer, Karl J.; Jameson, Heather T.; Thennakoon, Nishani; Leito, Ivo; Lõkov, Märt; Kütt, Agnes; Vianello, Robert et al.

Synthesis and Basicity Studies of Quinolino[7,8‑h]quinoline Derivatives // Journal of organic chemistry, 85 (2020), 11297-11308 doi:10.1021/acs.joc.0c01428 (međunarodna recenzija, članak, znanstveni)

CROSBI ID: 1099185 Za ispravke kontaktirajte CROSBI podršku putem web obrasca

Naslov
Synthesis and Basicity Studies of Quinolino[7,8‑h]quinoline Derivatives

Autori
Rowlands, Gareth J. ; Severinsen, Rebecca J. ; Buchanan, Jenna K. ; Shaffer, Karl J. ; Jameson, Heather T. ; Thennakoon, Nishani ; Leito, Ivo ; Lõkov, Märt ; Kütt, Agnes ; Vianello, Robert ; Despotović, Ines ; Radić, Nena ; Plieger, Paul G.

Izvornik
Journal of organic chemistry (0022-3263) 85 (2020); 11297-11308

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

Ključne riječi
Superbases

Sažetak
Quinolino[7, 8-h]quinoline is a superbasic compound, with a pKaH in acetonitrile greater than that of 1, 8-bis(dimethylaminonaphthalene) (DMAN), although its synthesis and the synthesis of its derivatives can be problematic. The use of halogen derivatives 4, 9-dichloroquinolino[7, 8-h]quinoline (16) and 4, 9-dibromoquinolino[7, 8-h]quinoline (17) as precursors has granted the formation of a range of substituted quinolinoquinolines. The basicity and other properties of quinolinoquinolines can be modified by the inclusion of suitable functionalities. The experimentally obtained pKaH values of quinolino[7, 8-h]quinoline derivatives show that N4, N4, N9, N9-tetraethylquinolino[7, 8- h]quinoline-4, 9-diamine (26) is more superbasic than quinolino[7, 8-h]quinoline. Computationally derived pKaH values of quinolinoquinolines functionalized with dimethylamino (NMe2), 1, 1, 3, 3- tetramethylguanidino (N=C(NMe2)2) or N, N, N′, N′, N ″, N″-hexamethylphosphorimidic triamido (N=P(NMe2)3) groups are significantly greater than those of quinolino[7, 8-h]quinoline. Overall, electron-donating functionalities are observed to increase the basicity of the quinolinoquinoline moiety, while the substitution of electron- withdrawing groups lowers the basicity.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA

Projekti:
HRZZ-IP-2014-09-3386 - Dizajn i sinteza novih dušikovih heterocikličkih fluorofora i fluorescentnih nanomaterijala kao kemijskih senzora za pH i metalne ione (iNFiNiTE–SENS) (Vianello, Robert, HRZZ - 2014-09) ( CroRIS)

Ustanove:
Institut "Ruđer Bošković", Zagreb

Profili:

Ines Despotović (autor)