A series of metal complexes of 2-aminobenzoquinoline prepared by C–H activation show molecular recognition effects. For example, ketones bound both by N–H⋯O hydrogen bonding and by coordination to a metal show selectivity of binding and dynamic properties not found when the hydrogen bonding function is omitted. N-heterocyclic carbenes (NHCs) are prepared by C–H activation reactions of imidazolium salts with the goal of understanding and using molecular recognition effects in homogeneous catalysis. Abnormal binding via C5 is seen in some cases.
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Robert H. Crabtree (2003) studied this question.
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