Download Heterocyclic Supramolecules II by Hiroyuki Suga (auth.), Kiyoshi Matsumoto, Naoto Hayashi PDF

By Hiroyuki Suga (auth.), Kiyoshi Matsumoto, Naoto Hayashi (eds.)

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Heterocyclic Supramolecules II

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O + N H . H N+ O _ 20 Fig. 4°) experimental fold angles recorded by us in the solid state. These angles are measured between the points indicated by the solid circles [50, 51] Supramolecular Host-Guest Chemistry 49 between 80° and 115° but, occasionally, extreme values are encountered. 0° in the apohost 19 crystal structure is the lowest that we have observed [50]. In this case, generation of an A-shaped molecular conformation leads to compact layers and generation of an efficient network of intermolecular halogen…π and aryl EF attractions.

But, when an electron-withdrawing 32 N. Hayashi et al. group is substituted onto the benzene, ∆ q will increase to negatively decrease MEP, so that basicity will be weakened again. Conclusively, substitution of an electronwithdrawing group will decrease basicity of the heteroaromatic moiety, whether the configuration of the complex is p stack or T-shaped. Mignon et al. also investigated influences of p stacking on the hydrogen-bonding acceptability of DNA/RNA bases, such as adenine, cytosine, uracil, and guanine [99], and found that, while hydrogen bond acceptabilities of those DNA/RNA bases are diminished by formation of p stacking in the optimized structures, they are enhanced in the actual structures.

When benzene was added into CCl4 solution of BC and IND, hypsochromic shifts of the NH vibration peak were observed. Changes when the other p molecules were added may be categorized into two types. The first is inertness of the peak position shift of the N–H vibration with increased association constant (K), which was observed when naphthalene and phenanthrene were used instead of benzene. The virtually constant N–H peak position shifts are indicative of the same magnitude of NH/p interactions of BC–benzene, BC–naphthalene, and BC–phenanthrene, and the increase of K results from the increased number of the acceptor sites (that is, benzene ring).

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