高等有机化学课件Chapter 1 Chemical Bonding.ppt

Crown Ether Complexes and Cryptates 穴合物 穴状配体 杯芳烃 Among other hosts for inclusion and/or clathrate compounds are deoxycholic acid, cholic acid, anthracene compounds, such as 34, dibenzo-24-crown-8, and the compound 35, which has been called a carcerand. When carcerandtype molecules trap ions or other molecules (called guests), the resulting complex is called a carciplex. It has been shown that in some cases, the motion of the guest within the carciplex is restricted. 瓜环 甘脲 The Rules of Resonance 1. All the canonical forms must be bona fide Lewis structures (see p. 14). For example, none of them may have a carbon with five bonds. 2. The positions of the nuclei must be the same in all the structures. This means that when we draw the various canonical forms, all we are doing is putting in the electrons in different ways. For this reason, shorthand ways of representing resonance are easy to devise: 3. All atoms taking part in the resonance, that is, covered by delocalized electrons, must lie in a plane or nearly so. This, of course, does not apply to atoms that have the same bonding in all the canonical forms. The reason for planarity is maximum overlap of the p orbitals. 4. All canonical forms must have the same number of unpaired electrons. Thus .CH2CHCHCH2. is not a valid canonical form for butadiene. 5. The energy of the actual molecule is lower than that of any form, obviously. Therefore, delocalization is a stabilizing phenomenon. 6. All canonical forms do not contribute equally to the true molecule. Each form contributes in proportion to its stability, the most stable form contributing most. Thus, for ethylene, the form tCH2CH2 has such a high energy compared to CH2CH2 that it essentially does not contribute at all. We have seen the argument that such structures do not contribute even in such cases as butadiene.36 Equivalent canonical forms, such as 1 and 2, contribute equally. The greater the number of significant structures that can be written and the more