Electron delocalization direct measurement

Despite nearly two centuries of intense scrutiny, aromaticity remains a unique research stimulus in chemistry. The concept of aromaticity is elusive it is not directly observable. Numerous indirect measures have been devised, based on the manifestations and ramifications of aromaticity. One of the most recent and widely accepted definitions [2] described aromaticity as a manifestation of electron delocalization in... 

Generalized valence bond interaction energies were computed for mono/poly-nitrogenous five- and six-membered heterocycles.203 Results that diverged from those obtained by other methods were obtained only for poly-nitrogenous systems such as pyridazine, benzotriazole, and tetrazole, which may confirm Bird s earlier finding123 204 that electron delocalization is not a stand-alone and direct measure of aromaticity for nitrogenous heterocyclic compounds. 

The concept of the hydrogen bond has a number of aspects in common with that of resonance (or electron delocalization) in molecular structures some of their qualitative effects were- well recognized before their present names were acquired and both phenomena are of very general occurrence. For their elucidation the same types of question have to be answered (i) What is the resultant electronic distribution and how can this be simply represented (ii) What stabilisation energy is achieved in particular systems in practice (id) Can this be calculated theoretically and so predicted for cases not yet directly measured ... 

The difference between the dipole moments of the aromatic compound and the corresponding tetrahydro derivative is called the mesomeric moment and represents a measure of the -electron delocalization. The mesomeric dipole moment is directed, in all the congener systems, from the heteroatom toward the ring. The values obtained (furan 1.03 D, thiophene 1.35 D, selenophene 1.29 D, tellurophene 1.17 D) are in excellent quantitative agreement with other aromaticity indices based on structural and magnetic properties12 (see discussion in Section II,C). 

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