CHEM266 Study Guide - Orbital Hybridisation, Lone Pair
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2 Dec 2012
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The energy of the actual molecule as a whole is lower than the energy of any single contributing resonance form: the lowering of energy is called resonance stabilization. The more equivalent resonance structures a molecule has, the more stable it is. As a whole, resonance structures have bonds of equal length and charges spread equally: resonance hybrid: a mixture of all the resonance structures. When n is already associated with a double bond, it"s lone pair is hybridized, and cannot be (cannot participate in resonance) delocalized. Therefore, in order for a lone pair delocalized (participate in resonance), it must not be hybridized; the lone pair must be located in the p orbital in order to participate in pi bonds. Even though this n has 4 surrounding things around it (3 atoms an 1 lone pair), it is sp2 hybridized instead of sp3.
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