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The resulting 24\u2010member macrocycles can be characterized by NMR spectroscopy, mass spectrometry, and single crystal X\u2010ray diffraction. In the solid state, both homodimers adopt a taco\u2010like conformation. Although each shows \u03c0\u2013\u03c0 stacking between the triazine rings, different patterns of hydrogen bonds emerge. The crystal structure of the isopropyl dimer shows that it includes two molecules of trifluoracetic acid per macrocycle. The trifluoroacetate anion charge balances the protonated triazines, which engage in bifurcated hydrogen bonds with the carbonyl acceptor of the distant glycine. This carbonyl also forms a hydrogen bond with the NH of the proximate glycine. The crystal structure of the benzyl derivative does not include trifluoracetic acid. Instead, two hydrogen bonds form, each between a glycine NH and the lone pair of the C=N nitrogen of the hydrazine group. In the solid state, both molecules present the alkyl side chains and morpholine groups in close proximity. A heterodimer is accessible in approximately statistical yields\u2014along with both homodimers\u2014by mixing the two protected monomers prior to subjecting them to deprotection.<\/jats:p>","DOI":"10.1002\/cbic.201800475","type":"journal-article","created":{"date-parts":[[2018,10,11]],"date-time":"2018-10-11T22:15:22Z","timestamp":1539296122000},"page":"241-246","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":11,"title":["Synthesis of Macrocycles Derived from Substituted Triazines"],"prefix":"10.1002","volume":"20","author":[{"given":"Akop","family":"Yepremyan","sequence":"first","affiliation":[{"name":"Department of Chemistry and Biochemistry Texas Christian University  2800 S. University Avenue Fort Worth TX 76109 USA"}]},{"given":"Arshad","family":"Mehmood","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Biochemistry Texas Christian University  2800 S. University Avenue Fort Worth TX 76109 USA"}]},{"given":"Parham","family":"Asgari","sequence":"additional","affiliation":[{"name":"Shimadzu Center of the University of Texas at Arlington  505 W. Nedderman Drive Arlington TX 76019 USA"}]},{"given":"Benjamin G.","family":"Janesko","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Biochemistry Texas Christian University  2800 S. University Avenue Fort Worth TX 76109 USA"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3195-4523","authenticated-orcid":false,"given":"Eric E.","family":"Simanek","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Biochemistry Texas Christian University  2800 S. 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