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Legon Fig. 18 The n-pair/π-pair model of furan together with the experimental geometries of furan· · ·HCl and furan· · ·ClF. Furan· · ·HCl, which has a planar geometry of C2v symmetry with HCl lying along the C2 axis, clearly obeys rule 3 but the observed face-on arrangement for furan· · ·ClF demonstrates that rule 3 is violated in this case. See Fig. 1 for key to the colour coding of atoms The behaviour of the n-pair/aromatic π-pair donors can be understood by considering the electric charge distributions for the series of heterocyclic molecules pyridine, furan and thiophene.
2 Angular Geometries of B· · ·ClF and B· · ·HCl in Which B is a π-Pair Donor According to the rules for predicting angular geometries of hydrogen-bonded complexes B· · ·HX, given earlier, the HX molecule lies along the local symmetry axis of a π orbital when B carries no non-bonding electron pairs and only π pairs. In this section, we examine whether this rule also applies to halogen-bonded complexes B· · ·XY. We consider first Lewis bases that offer only a single π pair. 1 B Carries a Single-π-Pair The experimentally determined geometries of the complexes of the simplest π electron donor, ethene, with HCl [128] and ClF [65] are displayed in Fig.
There is a polar flattening of the atom X in the molecule XY of the type suggested by Stone et al. [180]. This result has been shown to hold for the cases XY = Cl2 [174], BrCl [175], ClF [176] and ICl [178], but not for F2 , in which the F atom in the molecule appears (admittedly on the basis of only a few examples) to be more nearly spherical [177]. The second conclusion concerns the difference ∆r = rB· · · HX (Z · · · X) – rB· · · XY (Z · · · X) between the Z to X distances in the two series B· · ·HX and B· · ·XY.