Product Details of 78-39-7. Wang, X; Shyshov, O; Hanzevacki, M; Jager, CM; von Delius, M in [Wang, Xiang; Shyshov, Oleksandr; von Delius, Max] Univ Ulm, Inst Organ Chem & Adv Mat, Albert Einstein Allee 11, D-89081 Ulm, Germany; [Hanzevacki, Marko; Jager, Christof M.] Univ Nottingham, Dept Chem & Environm Engn, Univ Pk, Nottingham NG7 2RD, England; [Hanzevacki, Marko] Rudjer Boskovic Inst, Bijenicka 54, Zagreb 10000, Croatia published Ammonium Complexes of Orthoester Cryptands Are Inherently Dynamic and Adaptive in 2019.0, Cited 52.0. The Name is 1,1,1-Triethoxyethane. Through research, I have a further understanding and discovery of 78-39-7.
Fluxional chemical species such as bullvalene have been a valuable source of inspiration and fundamental insight into the nature of chemical bonds. A supramolecular analogue of bullvalene, i.e., a fluxional host-guest system, in which the ensemble of a well-defined host and guest is engaged in continuous, degenerate constitutional rearrangements, is still elusive, however. Here, we report experimental and computational evidence for guest-induced dynamic covalent rearrangements in the ammonium complexes of self-assembled orthoester cryptands. This unique behavior is made possible by the ammonium guest playing a dual role: it is sufficiently acidic to initiate dynamic covalent exchange reactions at the orthoester bridgeheads, and as a hydrogen bond donor it acts as a supramolecular template, governing the outcome of a multitude of possible intra- and intermolecular rearrangement reactions. One particularly striking example of inherent dynamic behavior was observed in host-guest complex [Na-4(+)subset of o-Me-2-2.1.1], which spontaneously rearranged into the larger and thermodynamically more stable complex [NH4+subset of o-Me-2-2.2.1], even though this process led to the formation of poor host o-Me-2-1.1.1 as a consequence of the excess of one subcomponent (diethylene glycol; 1 in our nomenclature). These inherently adaptive host-guest networks represent a unique platform for exploring the interrelationship between kinetic and thermodynamic stability. For instance, as a result of optimal NH4+ binding, complex [NH4+subset of o-Me-2-2.2.1] was found to be thermodynamically stable (negligible intermolecular rearrangements over weeks), whereas computational studies indicate that the compound is far from kinetically stable (intramolecular rearrangements).
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