Isolobal Principle

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Isolobal Principle

Postby harperlacroix1a » Sun Nov 25, 2018 7:39 pm

Can someone explain the isolobal principle/analogy to me? In problem 3.101 of the 6th edition, they replace bonds of C-H in the benzene structure with nitrogen but I'm confused as to why this is possible or why it happens.

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Re: Isolobal Principle

Postby Timothy_Yueh_4L » Sun Nov 25, 2018 7:53 pm

The isolobal principle states that an element or group of elements with similar shape, symmetry and radial extent; with approximately the same energy; and with the same number of electrons available for cluster bonding is able to replace another. In the case of benzene, the C-H can be replaced by N because nitrogen can provide the same aspects of symmetry as C-H. In the C-C bond, carbon forms a double and single bind with another carbon molecule and between the C-H bond, carbon forms a single bond with a hydrogen atom. Nitrogen provides the same properties in that it can double and single bond with a neighboring carbon or nitrogen and the resulting lone pair would be the equivalent of a C-H bond.

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