Naslov
The Proton Affinity of Some Substituted Naphtalenes

Autori
Eckert-Maksić, Mirjana ; Antol, Ivana ; Klessinger, Martin ; Maksić, Zvonimir B.

Izvornik
Journal of physical organic chemistry (0894-3230) 12 (1999); 597-604

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

Ključne riječi
Polysubstituted naphthalenes; Proton Affinity; Additivity rule; Ab initio calculations

Sažetak
The absolute proton affinity (PA) pertaining aromatic carbons of the monosubstituted naphtalenes involving CH3, OH, CHO, NO2 and Cl substituents is calculated at the MP2(fc)/6-31G**//HF/6-31G* + ZPVE(HF/6-31G*) level of theory. Increments corresponding to unsubstituted positions within the naphtalene skeleton are estimated. They can be used in estimating PAs in multiply substituted naphtalenes by using a simple additivity rule based on the independent substituent approximation (ISA). It is shown that increments are good indicators of the electrophylic substitution reactivity. The proton affinities of a large number of polysubstituted methylnaphtalenes is examined employing the additivity formula. It is found that the protonated forms, which exhibit the largest PAs corresponding to arenium ions observed by the NMR technique in the superacid media.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

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