{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,18]],"date-time":"2026-08-18T04:58:29Z","timestamp":1787029109504,"version":"build-2736575974"},"reference-count":72,"publisher":"MDPI AG","issue":"3","license":[{"start":{"date-parts":[[2025,1,28]],"date-time":"2025-01-28T00:00:00Z","timestamp":1738022400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"The Ogasawara Toshiaki Memorial Foundation Grant","award":["22K05106"],"award-info":[{"award-number":["22K05106"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Complete assignments of the 1H and 13C NMR chemical shifts for the monoterpenes, borneol 1a and isoborneol 2a, as well as their derivatives (1b\u20131g and 2b\u20132g), in which the secondary hydroxy group is protected with various protecting groups, have been made in various solvents. Upon protection of the hydroxy groups in 1a and 2a, many protons and carbons within the bicyclic ring exhibited downfield or upfield shifts in their chemical shift values, facilitating the unambiguous assignments of these protons and carbons. These chemical shift values also showed excellent correlations with those obtained from density functional theory (DFT) calculations. Furthermore, the anisotropic effect of the benzene ring was estimated by the analysis of the iso-chemical shielding surface (ICSS) resulting from substituents introduced to the hydroxyl groups of 1a and 2a.<\/jats:p>","DOI":"10.3390\/molecules30030597","type":"journal-article","created":{"date-parts":[[2025,1,29]],"date-time":"2025-01-29T03:26:10Z","timestamp":1738121170000},"page":"597","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["Complete Assignments of 1H and 13C NMR Chemical Shift Changes Observed upon Protection of Hydroxy Group in Borneol and Isoborneol and Their DFT Verification"],"prefix":"10.3390","volume":"30","author":[{"given":"Baohe","family":"Lyu","sequence":"first","affiliation":[{"name":"Graduate School of Science and Technology, Hiroshima Institute of Technology, 2-1-1 Miyake, Saeki-ku, Hiroshima 731-5193, Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0009-5482-2038","authenticated-orcid":false,"given":"Yoshikazu","family":"Hiraga","sequence":"additional","affiliation":[{"name":"Graduate School of Science and Technology, Hiroshima Institute of Technology, 2-1-1 Miyake, Saeki-ku, Hiroshima 731-5193, Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8180-6297","authenticated-orcid":false,"given":"Ryukichi","family":"Takagi","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Graduate School of Advanced Science and Engineering, Hiroshima University, 1-3-1 Kagamiyama, Higashi-Hiroshima 739-8526, Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6385-5274","authenticated-orcid":false,"given":"Satomi","family":"Niwayama","sequence":"additional","affiliation":[{"name":"Graduate School of Engineering, Muroran Institute of Technology, 27-1 Mizumoto-cho, Muroran 050-8585, Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2025,1,28]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"S77","DOI":"10.1016\/j.fct.2008.06.031","article-title":"Fragrance material review on borneol","volume":"46","author":"Bhatia","year":"2008","journal-title":"Food Chem. 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