Hückelovo pravidlo
Aby byla daná latka aromatická, musí být molekula planární, monocyklická, mít dokonale konjugovaný systém vazeb a splňovat právě onu Hückelovu podmínku. Ta říká, že počet pí-elektronů ve sloučenině musí být roven číslu 4n+2, tedy matematicky P= 4n+2, kde P je počet pí-elektronů a n je libovolné celé nezáporné číslo.
Ovšem proč zrovna 4n+2??? Co je na této kombinaci tak speciálního? Proč tedy zrovna 2, 6, 10, 14... pí-elektronů vede k aromaticitě a poměrně vysoké stabilitě, zatímco ostatní kombinace vedou k větší či menší nestabilitě. Odpověď se skrývá v "tajemné" teorii molekulových orbitalů (MO).
Pokud se totiž spočítají energetické hladiny molekulových orbitalů pro cyklické konjugované molekuly, ukáže se, že vždy existuje jeden nejníže ležící MO, nad kterým existují MO v degenerovaných párech. Tedy, při zaplňováníí MO je vždy potřeba dvou elektronů na zaplnění nejníže ležícího osamoceného MO a poté vždy čtyř elektronů na zaplnění každé z n následujících energetických hladin - dohromady tedy 2 + 4n. Každý jiný počet zanechá energetickou hladinu částečně nezaplněnou a tedy méně stabilní.

OBR: Molekulové orbitaly pro benzen:
1. Šipka vlevo ukazuje růst energie systému
2. Šest nedegenerovaných 2p atomových orbitalů (AO) šesti atomů uhlíku v cyklu benzenu s jedním elektronem v každém z nich
3. Při konjugaci a vzniku molekulových orbitalů vznikají tři vazebné MO o nižší energii než měly puvodní AO (dva jsou degenerované) a tři protivazebné MO o vyšší energii než měly původní AO (dva jsou opět degenerované)
4. Vazebné MO jsou zaplněny elektrony - je vidět, proč jich musí být právě 4n + 2 - tak dojde k zaplnění všech vazebných MO, kdyby jich byl jiný počet, některá místa by byla zbytečně volná.
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???
(ZUZU, 5. 6. 2012 16:51)
"Aby byla daná latka aromatická, musí být molekula planární, monocyklická......"
Nechapem vsak naftalen alebo antracen su tiez aromaticke uhlovodiky a nie su monocyklicke... tak ako to potom je s tym Huckelovym pravidlom???
Re: ???
(tom, 8. 6. 2012 9:33)
je hezke, ze nad tim uvazujete. samozrejme mate pravdu, molekula nemusi byt monocyklicka, viz vaze priklady.
dulezita je pouze ta planarita, mit 4n+2 elektronu v p-orbitalech a vsechny atomy se musi podilet na tvorbe delokalizovaneho systemu bud volnym el. parem anebo p-orbitalem
Re: ???
(Ondra, 23. 3. 2014 18:46)Ta podminka je spatne. Nejde o monocykly, ale vseobecne cykly a tudiz i o kondenzovane polycykly, jako treba naftalen, anthracen apod.
?
(inka , 2. 5. 2013 13:50)Mohla bych se zeptat, jaké je odůvodnění rozdílu aromaticity u cyklopropenu/-idu/-ylia, když jestli to chápu správně počet "pi-elektronu" je stejný?
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