{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,1,18]],"date-time":"2026-01-18T21:02:32Z","timestamp":1768770152308,"version":"3.49.0"},"reference-count":48,"publisher":"Wiley","issue":"7","license":[{"start":{"date-parts":[[2009,4,16]],"date-time":"2009-04-16T00:00:00Z","timestamp":1239840000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Magnetic Reson in Chemistry"],"published-print":{"date-parts":[[2009,7]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p><jats:sup>1<\/jats:sup>H and <jats:sup>13<\/jats:sup>C NMR chemical shift calculations using the density functional theory\u2013gauge including\/invariant atomic orbitals (DFT\u2013GIAO) approximation at the B3LYP\/6\u2010311G++(d,p) level of theory have been used to assign both natural diastereoisomers of 6\u03b2\u2010hydroxyhyoscyamine. The theoretical chemical shifts of the <jats:sup>1<\/jats:sup>H and <jats:sup>13<\/jats:sup>C atoms in both isomers were calculated using a previously determined conformational distribution, and the theoretical and experimental values were cross\u2010compared. For protons, the obtained average absolute differences and root mean square (rms) errors for each comparison showed that the experimental chemical shifts of dextrorotatory and levorotatory 6\u03b2\u2010hydroxyhyoscyamines correlated well with the theoretical values calculated for the (3<jats:italic>R<\/jats:italic>,6<jats:italic>R<\/jats:italic>,2\u2032<jats:italic>S<\/jats:italic>) and (3<jats:italic>S<\/jats:italic>,6<jats:italic>S<\/jats:italic>,2\u2032<jats:italic>S<\/jats:italic>) configurations, respectively, whereas for <jats:sup>13<\/jats:sup>C atoms the calculations were unable to differentiate between isomers. The nature of the relatively large chemical shift differences observed in nuclei that share similar chemical environments between isomers was asserted from the same calculations. It is shown that the anisotropic effect of the phenyl group in the tropic ester moiety, positioned under the tropane ring, has a larger shielding effect over one ring side than over the other one. Copyright \u00a9 2009 John Wiley &amp; Sons, Ltd.<\/jats:p>","DOI":"10.1002\/mrc.2432","type":"journal-article","created":{"date-parts":[[2009,4,16]],"date-time":"2009-04-16T04:33:56Z","timestamp":1239856436000},"page":"578-584","source":"Crossref","is-referenced-by-count":26,"title":["DFT\u2010GIAO <sup>1<\/sup>H and <sup>13<\/sup>C NMR prediction of chemical shifts for the configurational assignment of 6\u03b2\u2010hydroxyhyoscyamine diastereoisomers"],"prefix":"10.1002","volume":"47","author":[{"given":"Marcelo A.","family":"Mu\u00f1oz","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Pedro","family":"Joseph\u2010Nathan","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2009,4,16]]},"reference":[{"key":"e_1_2_1_2_2","first-page":"1","volume-title":"The Alkaloids","author":"Lounasmaa 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