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Ber."},{"key":"ref12\/cit12a","first-page":"5","volume":"226","author":"Davis A. P.","year":"1999","journal-title":"Chem.Commun."},{"key":"ref12\/cit12b","doi-asserted-by":"crossref","first-page":"4933","DOI":"10.1016\/S0040-4039(01)00880-2","volume":"42","author":"Prohens R.","year":"2001","journal-title":"Tetrahedron Lett."},{"key":"ref12\/cit12c","doi-asserted-by":"crossref","first-page":"2302","DOI":"10.1021\/jo035546t","volume":"69","author":"Rotger M. C.","year":"2004","journal-title":"J. Org. Chem."},{"key":"ref13\/cit13","unstructured":"The addition of Br\u2212or I\u2212to1(or2)did not lead to any solvent-polarity dependent NMR spectral shifts. For F\u2212, CH3CO2\u2212, and H2PO4\u2212there were no spectral changes in CHCl3but in CH3CN, a 77 nm bathochromic shift in the UV\u2212vis spectra was identical to that generated by the addition of OH\u2212indicating deprotonation of the squaramide (see theSupporting Information)."},{"key":"ref14\/cit14","unstructured":"Similar spectral shifts were observed in solvent mixtures such as 9:1 (v\/v) CD3CN\/DMSO-d6or CD3CN\/CDCl3(9:1) but not in neat DMSO-d6or pyridine-d5. Compounds1and2were insoluble in methanol-d4."},{"key":"ref15\/cit15","doi-asserted-by":"crossref","first-page":"4003","DOI":"10.1021\/ol035624z","volume":"5","author":"Kim Y. K.","year":"2003","journal-title":"Org. Lett."},{"key":"ref16\/cit16","unstructured":"Aggregation of the uncomplexed squaramides was examined separately but was considered unlikely since in the NMR spectra of1and2only minor changes (\u0394\u03b4 < 0.01) were observed over a 10-fold (0.5\u22125 mM) variation in concentration in both CDCl3and CD3CN. For3, a linear relationship between absorbance and concentration (20\u22122 \u03bcM) excluded aggregation."},{"key":"ref17\/cit17","first-page":"928","volume":"180","author":"Job P.","year":"1925","journal-title":"Compt. Rend."},{"key":"ref18\/cit18","unstructured":"Although significant changes were observed in both the NH and the aromatic regions of the NMR spectra, tracking of the latter signals was difficult due to peak overlap."},{"key":"ref19\/cit19","doi-asserted-by":"crossref","first-page":"9","DOI":"10.1016\/0022-2860(92)80205-V","volume":"271","author":"Denisov G. S.","year":"1992","journal-title":"J. Mol. Struct."},{"key":"ref20\/cit20","unstructured":"Numerous attempts to record IR spectra of1and2in CH3CN, as additional evidence for hydrogen bond disruption, were not fruitful. 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