{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,17]],"date-time":"2026-08-17T22:20:10Z","timestamp":1787005210844,"version":"build-2736575974"},"reference-count":54,"publisher":"AIP Publishing","issue":"19","content-domain":{"domain":["pubs.aip.org"],"crossmark-restriction":true},"short-container-title":[],"published-print":{"date-parts":[[2008,5,21]]},"abstract":"<jats:p>The characteristics of the interaction between phenol and acetonitrile, methyl fluoride and methyl chloride were studied. The most stable structures for clusters containing one or two CH3X molecules and one phenol moiety were located by means of ab initio and density functional theory calculations. Phenol-acetonitrile dimer presents two almost equally stable structures; one of them is a typical linearly hydrogen bonded minimum, whereas in the other one, a C\u2013H\u22ef\u03c0 contact is established accompanied by a distorted O\u2013H\u22efN hydrogen bond. Although the latter minimum presents the larger interaction energy, deformation effects favor the formation of the linear hydrogen bonded one. In complexes with methyl fluoride and methyl chloride, this arrangement is the most stable structure and no linear hydrogen bonded structures were located. Our best estimates for the interaction energies amount to \u221227.8, \u221221.6, and \u221219.7kJ\u2215mol for clusters of phenol with acetonitrile, methyl fluoride, and methyl chloride, respectively. The main contribution to the stabilization of these clusters is of electrostatic nature, although in structures where a C\u2013H\u22ef\u03c0 contact is present, the dispersion contribution is also significant. In clusters formed by phenol and two CH3X units, the most stable arrangement corresponds to a head to tail disposal with O\u2013H\u22efX, C\u2013H\u22efX, and C\u2013H\u22ef\u03c0 contacts forming a cycle. Only for this type of arrangement, three body effects are non-negligible even though they constitute a minor effect. The results also indicate that interactions with methyl fluoride and methyl chloride are of similar intensity, although weaker than with acetonitrile. Significant frequency shifts are predicted for the O\u2013H stretching, which increase when increasing the number of CH3X molecules.<\/jats:p>","DOI":"10.1063\/1.2919128","type":"journal-article","created":{"date-parts":[[2008,5,22]],"date-time":"2008-05-22T18:54:14Z","timestamp":1211482454000},"update-policy":"https:\/\/doi.org\/10.1063\/aip-crossmark-policy-page","source":"Crossref","is-referenced-by-count":12,"title":["Study of the interaction in clusters formed by phenol and CH3X\u2008(X=CN,F,Cl) molecules"],"prefix":"10.1063","volume":"128","author":[{"given":"Enrique M.","family":"Cabaleiro-Lago","sequence":"first","affiliation":[{"name":"Universidade de Santiago de Compostela 1 Departamento de Qu\u00edmica F\u00edsica, Facultade de Ciencias, , Campus de Lugo, Avda. 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