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0344668790
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note
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w = 0.1186 (all data), CCDC 217630. See the Supporting Information for CIF files.
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12
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0035820052
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3Bpyrr = lithium pyrrolidinoborohydride was synthesized according to the literature; see: Thomas, L. S.; Collins, C. J.; Cuzens, J. R.; Spiciarich, D.; Goralski, C. T.; Singaram, B. J. Org. Chem. 2001, 66, 1999.
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Singaram, B.6
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16
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0345531060
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note
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We performed molecular modeling calculations, using HyperChem, v7.1 in order to calculate the rotational barrier for the C2-C6 and C11-C12 bonds (numbering of the atoms is according with the X-ray structure). We used the di-tert-butyl analogues of both 7 and 8 so as to keep the calculations tractable. The PM3 semiempirical method in conjunction with the Conformation Search module was used to determine the structure with the minimum energy. The criteria for convergence was a difference in energy between two sequential structures below 0.01 kcal/(A mol). The results of these calculation show that the rotational barrier is 37% higher in the case of 8 vs 7. This is consistent with preorganization and conformation affects being significant aryl bridged dipyrrole anion receptors, and more so in the case of the larger dipyrrolylquinoxalines than in the smaller dipyrrolylpyrazines.
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