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In this paper, structurally related architectures featuring two alternative hydrogen bonding motifs were compared to ascertain the structural and functional origin of their binding differences and the advantages that can be expected in monosaccharide recognition. A set of structurally related macrocyclic receptors were prepared, and their binding properties were measured by NMR and ITC techniques in chloroform vs a common saccharidic target, namely, the \u03b2\u2010octyl glycoside of D\u2010glucose. Results showed that the diaminocarbazolic motif, recently reported as the constituting unit of highly effective receptors for saccharides in water, is a superior hydrogen bonding motif compared to the previously described diaminopyrrolic motif, which was successfully employed in molecular recognition of carbohydrates in polar organic solvents, due to intrinsic structural and functional factors, rather than to hydrophobic contributions. In addition, the occurrence of a rare example of a thermodynamic template effect exerted by the beta\u2010glucoside has been ascertained, enhancing the synthesis outcome of the otherwise low yielding preparation of the described macrocyclic receptors.<\/jats:p>","DOI":"10.1002\/cphc.201900907","type":"journal-article","created":{"date-parts":[[2019,12,2]],"date-time":"2019-12-02T22:30:27Z","timestamp":1575325827000},"page":"257-262","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":25,"title":["A Preorganized Hydrogen\u2010Bonding Motif for the Molecular Recognition of Carbohydrates"],"prefix":"10.1002","volume":"21","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-6155-4926","authenticated-orcid":false,"given":"Oscar","family":"Francesconi","sequence":"first","affiliation":[{"name":"Department of Chemistry \u201cUgo Schiff\u201d and INSTM University of Florence Polo Scientifico e Tecnologico  50019 Sesto Fiorentino, Firenze Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Federico","family":"Cicero","sequence":"additional","affiliation":[{"name":"Department of Chemistry \u201cUgo Schiff\u201d and INSTM University of Florence Polo Scientifico e Tecnologico  50019 Sesto Fiorentino, Firenze Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6312-3230","authenticated-orcid":false,"given":"Cristina","family":"Nativi","sequence":"additional","affiliation":[{"name":"Department of Chemistry \u201cUgo Schiff\u201d and INSTM University of Florence Polo Scientifico e Tecnologico  50019 Sesto Fiorentino, Firenze Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9763-3263","authenticated-orcid":false,"given":"Stefano","family":"Roelens","sequence":"additional","affiliation":[{"name":"Department of Chemistry \u201cUgo Schiff\u201d and INSTM University of Florence Polo Scientifico e Tecnologico  50019 Sesto Fiorentino, Firenze Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2020,1,9]]},"reference":[{"key":"e_1_2_6_1_1","unstructured":"\u00a0"},{"key":"e_1_2_6_2_2","unstructured":"A.\u2005P. 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