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The proton, lacking any electrons, is infinitely hard. In solution it does not exist as an independent entity but contributes to the hardness of some protonated species. Metal ion hardness increases with oxidation state as the electron cloud contracts with the removal of each successive electron. All these as 22 23 24 R. G. Pearson and J. Songstad, J. Am. Chem. , 89, 1827 (1967); R. G. Pearson, J. Chem. , 45, 581, 643 (1968). R. G. Pearson, Inorg. Chim. Acta, 240, 93 (1995). P. K. Chattaraj, H.
In this case, the two charged structures are not equivalent. Fig. 5. Contour map of electron density for 1,3butadiene in the plane of the molecule. Electron density was calculated at the HF/6-311G level. Dayles, J. Compt. , 22, 545-559 (2001). Structure B is a better structure than C because it places the negative charge on a more electronegative element, oxygen (resonance criteria 3c). Structure D accounts for the polarity of the C=O bond. The real molecular structure should then reflect the character of A > B ∼ D > C ∼ E.
Cedillo, R. G. M. Arnett, J. Org. , 60, 4707 (1995). P. R. Reddy, T. V. R. Rao, and R. Viswanath, J. Am. Chem. , 111, 2914 (1989). R. J. W. Le Fevre, Adv. Phys. Org. , 3, 1 (1965). K. von Auwers, Chem. , 68, 1635 (1935); A. I. Vogel, J. Chem. , 1842 (1948); J. W. , 235, 1 (1986); J. W. , 236, 233 (1986). 2. 12 a. From R J. W. Le Fevre, Adv. Phys. Org. , 3, 1 (1965). The concepts of electronegativity, polarizability, hardness, and softness are all interrelated. For the kind of qualitative applications we make in discussing reactivity, the concept that initial interactions between reacting molecules can be dominated by either partial electron transfer and bond formation (soft reactants) or by electrostatic interaction (hard reactants) is an important generalization.