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Herein, HF forms the classical red\u2010shifting HBs whereas CHF<jats:sub>3<\/jats:sub> forms the unconventional blue\u2010shifting HBs with the cyclic ketones. The red\u2010shifting F\uf8ffH\u00b7\u00b7\u00b7O HBs are found to be characterized by predominantly shared\u2010shell interaction as contrary to the closed\u2010shell (electrostatic) interaction governing the blue\u2010shifting F<jats:sub>3<\/jats:sub>C\uf8ffH\u00b7\u00b7\u00b7O HBs. This is seen to be consistent with the dominance of hyperconjugative ( charge transfer) effect over the rehybridization effect underlying the redshifting F\uf8ffH\u00b7\u00b7\u00b7O HBs, while the reverse situation prevails for blueshifting F<jats:sub>3<\/jats:sub>C\uf8ffH\u00b7\u00b7\u00b7O HBs. The geometry and electronic structure parameters of the cyclic ketones (HB acceptors) show that the polarity of the carbonyl (C\uf8feO) moiety can be correlated with the ring size to rationalize the electrostatic stabilization of the HBs. The performance of the three density functionals is compared for characterizing the HBs in combination with the triple\u2010\u03b6 basis set 6\u2010311++g(d,p).<\/jats:p>","DOI":"10.1002\/cphc.202500057","type":"journal-article","created":{"date-parts":[[2025,4,19]],"date-time":"2025-04-19T01:35:56Z","timestamp":1745026556000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":10,"title":["Red\u2010 and Blue\u2010shifting Hydrogen Bonds of Cyclic Ketones of Varying Ring Sizes with HF and CHF<sub>3<\/sub>: Comparison of the Results of B3LYP, O3LYP, and M06\u20102X Functionals"],"prefix":"10.1002","volume":"26","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-3839-2113","authenticated-orcid":false,"given":"Bijan K.","family":"Paul","sequence":"first","affiliation":[{"name":"Department of Chemistry Mahadevananda Mahavidyalaya  Kolkata 700 120 India"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2025,5,7]]},"reference":[{"key":"e_1_2_7_2_1","doi-asserted-by":"publisher","DOI":"10.1007\/978-3-642-85135-3"},{"key":"e_1_2_7_3_1","volume-title":"An Introduction to Hydrogen Bonding","author":"Jeffrey G. 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