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Molecules 2017, 22(2), 227; doi:10.3390/molecules22020227

Theoretical Study of Intramolecular Interactions in Peri-Substituted Naphthalenes: Chalcogen and Hydrogen Bonds

1
Irish Centre of High-End Computing, Grand Canal Quay, Dublin 2, Ireland
2
Instituto de Química Médica, CSIC, Juan de la Cierva, 3, E–28006 Madrid, Spain
*
Author to whom correspondence should be addressed.
Received: 14 December 2016 / Accepted: 26 January 2017 / Published: 2 February 2017
(This article belongs to the Special Issue Intramolecular Hydrogen Bonding 2017)
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Abstract

A 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. View Full-Text
Keywords: chalcogen bonds; non-covalent interactions; MP2; interaction energy; intramolecular interactions; hydrogen bonds chalcogen bonds; non-covalent interactions; MP2; interaction energy; intramolecular interactions; hydrogen bonds
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Sánchez–Sanz, G.; Alkorta, I.; Elguero, J. Theoretical Study of Intramolecular Interactions in Peri-Substituted Naphthalenes: Chalcogen and Hydrogen Bonds. Molecules 2017, 22, 227.

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