Nalazite se na CroRIS probnoj okolini. Ovdje evidentirani podaci neće biti pohranjeni u Informacijskom sustavu znanosti RH. Ako je ovo greška, CroRIS produkcijskoj okolini moguće je pristupi putem poveznice www.croris.hr
izvor podataka: crosbi

Strong acidity of some polycyclic aromatics annelated to the cyclopentadiene moiety and their cyano derivatives - A density functional B3LYP study (CROSBI ID 113012)

Prilog u časopisu | izvorni znanstveni rad | međunarodna recenzija

Vianello, Robert ; Maksić, Zvonimir Strong acidity of some polycyclic aromatics annelated to the cyclopentadiene moiety and their cyano derivatives - A density functional B3LYP study // European journal of organic chemistry, 16 (2005), 3571-3580-x

Podaci o odgovornosti

Vianello, Robert ; Maksić, Zvonimir

engleski

Strong acidity of some polycyclic aromatics annelated to the cyclopentadiene moiety and their cyano derivatives - A density functional B3LYP study

Acidity of the parent 1H-benz[f]indene (1a), 1H-benz[e]indene (2a), 1H-benz[fg]acenaphthylene (3a) and 1H-cyclopenta[l]phenanthrene (4a) and their polycyano derivatives is examined in the gas-phase and DMSO by the DFT-B3LYP methods. It is shown that pure hydrocarbons exhibit modest acidities, whereas dramatic increase in acidity is observed upon multiple cyanation leading to hyperstrong neutral organic superacids. It is found that polycyano derivatives undergo prototropic tautomerism with a consequence that the most stable tautomer contains keteneimine C=C=NH functionality. The origin of their highly pronounced acidity is identified as a very strong anionic resonance effect, cooperatively and efficiently assisted by a large number of CN groups. It is stressed that the polycyanated anions are very stable and have highly dispersed negative charge, which should lead to a low nucleophilicity and weak coordinating properties, thus making them potentially very useful in academic research and technological applications.

anionic resonance; acidity; polarized continuum model; substituent effects; superacidic systems

nije evidentirano

nije evidentirano

nije evidentirano

nije evidentirano

nije evidentirano

nije evidentirano

Podaci o izdanju

16

2005.

3571-3580-x

objavljeno

1434-193X

Povezanost rada

Kemija

Indeksiranost