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Competition between intramolecular hydrogen and pnictogen bonds in protonated systems

AuthorsSánchez-Sanz, Goar; Trujillo, Cristina; Alkorta, Ibon CSIC ORCID ; Elguero, José CSIC ORCID
KeywordsHydrogen bonds
Non-covalent interactions
Interaction energy
Intramolecular interactions
Pnictogen bonds
Issue Date2016
CitationTheoretical Chemistry Accounts 135 (2016)
AbstractA theoretical study of the competition between hydrogen (HB) and pnictogen bonds (ZB) in three different families of compounds, (Z)-1,2-disubstituted ethenes (Eth), 1,2-disubstituted benzenes (Phe) and 1,8-disubstituted naphthalenes (Naph), with a charged group, ZH and a neutral one, Z′H (Z, Z′ = N, P, As) as interacting moieties, has been carried out. In those structures with a NH motif, intramolecular hydrogen bond structures are minima while pnictogen interactions are transition states. The opposite is true for PH and AsH moieties. An analysis of isodesmic energies (E), interaction energies (E) and deformation energies (E) shows that in Eth derivatives, the most stable compound corresponds to P–N ZB while in the Phe and Naph ones, the N–N HB interaction presents the largest negative isodesmic energy. Also, Eth and Phe derivatives show negative E values for all the compounds under study; however, in some cases of Naph derivatives positive isodesmic energies have been found. The Atoms in Molecules (AIM) analysis of the electron density, natural bond orbital (NBO) second-order orbital energies and electron density shift maps (EDS) have been used to better understand these intramolecular interactions.
DescriptionThe online version of this article (doi:10.1007/s00214-016-1895-8) contains supplementary material, which is available to authorized users.
Publisher version (URL)
Identifiersdoi: 10.1007/s00214-016-1895-8
issn: 1432-881X
e-issn: 1432-2234
Appears in Collections:(IQM) Artículos

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