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Title

Theoretical study of intramolecular interactions in peri-substituted naphthalenes: Chalcogen and hydrogen bonds

AuthorsSánchez-Sanz, Goar; Alkorta, Ibon ; Elguero, José
KeywordsMP2
non-covalent interactions
hydrogen bonds
intramolecular interactions
interaction energy
chalcogen bonds
Issue Date2017
PublisherMolecular Diversity Preservation International
CitationMolecules 22 (2017)
AbstractA theoretical study of the peri interactions, both intramolecular hydrogen (HB) and chalcogen bonds (YB), in 1-hydroxy-8YH-naphthalene, 1,4-dihydroxy-5,8-di-YH-naphthalene, and 1,5-dihydroxy-4,8-di-YH-naphthalene, with Y = O, S, and Se was carried out. The systems with a OH:Y hydrogen bond are the most stable ones followed by those with a chalcogen O:Y interaction, those with a YH:O hydrogen bond (Y = S and Se) being the least stable ones. The electron density values at the hydrogen bond critical points indicate that they have partial covalent character. Natural Bond Orbital (NBO) analysis shows stabilization due to the charge transfer between lone pair orbitals towards empty Y-H that correlate with the interatomic distances. The electron density shift maps and non-covalent indexes in the different systems are consistent with the relative strength of the interactions. The structures found on the CSD were used to compare the experimental and calculated results.
Publisher version (URL)http://dx.doi.org/10.3390/molecules22020227
URIhttp://hdl.handle.net/10261/148214
DOI10.3390/molecules22020227
Identifiersdoi: 10.3390/molecules22020227
issn: 1420-3049
e-issn: 1420-3049
Appears in Collections:(IQM) Artículos
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