{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,29]],"date-time":"2026-09-29T02:50:32Z","timestamp":1790650232432,"version":"4.1.0"},"reference-count":78,"publisher":"MDPI AG","issue":"13","license":[{"start":{"date-parts":[[2025,6,21]],"date-time":"2025-06-21T00:00:00Z","timestamp":1750464000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Ministry of Science, Technological Development, and Innovation of the Republic of Serbia","award":["451-03-137\/2025-03\/200146"],"award-info":[{"award-number":["451-03-137\/2025-03\/200146"]}]},{"name":"Ministry of Science, Technological Development, and Innovation of the Republic of Serbia","award":["451-03-136\/2025-03\/200146"],"award-info":[{"award-number":["451-03-136\/2025-03\/200146"]}]},{"name":"Ministry of Science, Technological Development, and Innovation of the Republic of Serbia","award":["451-03-137\/2025-03\/200125"],"award-info":[{"award-number":["451-03-137\/2025-03\/200125"]}]},{"name":"Ministry of Science, Technological Development, and Innovation of the Republic of Serbia","award":["451-03-136\/2025-03\/200125"],"award-info":[{"award-number":["451-03-136\/2025-03\/200125"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>This study investigates the structural and energetic properties of hydrogen-bonded complexes between indole and a range of aliphatic, cyclic, and aromatic ketones using a combined vibrational spectroscopic and quantum-chemical approach. FTIR measurements in CCl4 revealed redshifts in the N-H stretching vibration of indole upon complexation, with formation constants (Ka) ranging from 0.3 to 6.6 M\u22121. Cyclohexanone displayed the strongest binding, while benzophenone exhibited the weakest interaction. Quantum-chemical calculations, employing CREST and MMFF94 conformational sampling, along with M06-2X\/6-311++G(d,p) optimizations, confirmed the formation of hydrogen bonds and additional weak interactions that govern the stability of the complex. QTAIM analysis revealed moderate closed-shell hydrogen bonds with electron densities at the bond critical points (\u03c1) ranging from 0.010 to 0.019 a.u. and potential energy densities (V) from \u221218.4 to \u221236.4 kJ mol\u22121. Multivariate regression analysis established strong correlations (R2 = 0.928 and 0.957) between experimental binding constants and theoretical descriptors, including binding energy, NBO charge on oxygen atom, ionization potential, and electrophilicity index, highlighting the interplay between geometric, electronic, and global reactivity factors. This comprehensive study underlines the predictive power of spectroscopic and quantum descriptors for assessing hydrogen bonding in biologically relevant systems.<\/jats:p>","DOI":"10.3390\/molecules30132685","type":"journal-article","created":{"date-parts":[[2025,6,23]],"date-time":"2025-06-23T04:50:05Z","timestamp":1750654205000},"page":"2685","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":4,"title":["Vibrational Spectroscopic and Quantum-Chemical Study of Indole\u2013Ketone Hydrogen-Bonded Complexes"],"prefix":"10.3390","volume":"30","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-4018-8461","authenticated-orcid":false,"given":"Branislav","family":"Jovi\u0107","sequence":"first","affiliation":[{"name":"Faculty of Sciences, University of Novi Sad, Trg Dositeja Obradovi\u0107a 3, 21000 Novi Sad, Serbia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0008-7032-6205","authenticated-orcid":false,"given":"Nata\u0161a","family":"Negru","sequence":"additional","affiliation":[{"name":"Faculty of Sciences, University of Novi Sad, Trg Dositeja Obradovi\u0107a 3, 21000 Novi Sad, Serbia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8127-5396","authenticated-orcid":false,"given":"Du\u0161an","family":"Dimi\u0107","sequence":"additional","affiliation":[{"name":"Faculty of Physical Chemistry, University of Belgrade, Studentski Trg 12-16, 11000 Belgrade, Serbia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1626-1881","authenticated-orcid":false,"given":"Branko","family":"Kordi\u0107","sequence":"additional","affiliation":[{"name":"Faculty of Sciences, University of Novi Sad, Trg Dositeja Obradovi\u0107a 3, 21000 Novi Sad, Serbia"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2025,6,21]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"419","DOI":"10.1016\/j.bbamem.2013.10.011","article-title":"Importance of Indole NH Hydrogen Bonding in the Organization and Dynamics of Gramicidin Channels","volume":"1838","author":"Chaudhuri","year":"2014","journal-title":"Biochim. 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