structural:scholar_edition, information:extraction, linguistic:translation
Charge delocalization

In the case of ions it is common to speak about delocalized charge (charge delocalization). An example of delocalized charge in ions can be found in the carboxylate group, wherein the negative charge is centered equally on the two oxygen atoms. Charge delocalization in anions is an important factor determining their reactivity (generally: the higher the extent of delocalization the lower the reactivity) and, specifically, the acid strength of their conjugate acids. As a general rule, the better delocalized is the charge in an anion the stronger is its conjugate acid. For example, the negative charge in perchlorate anion (ClO) is evenly distributed among the symmetrically oriented oxygen atoms (and a part of it is also kept by the central chlorine atom). This excellent charge delocalization combined with the high number of oxygen atoms (four) and high electronegativity of the central chlorine atom leads to perchloric acid being one of the strongest known acids with a p K value of −10. The extent of charge delocalization in an anion can be quantitatively expressed via the WAPS (weighted average positive sigma) parameter parameter and an analogous WANS (weighted average negative sigma) parameter is used for cations.