title: Behavior of carboxylic acids upon complexation with beryllium compounds.
abstract: A significant acidity enhancement and changes on aromaticity were previously observed in squaric acid and its derivatives when beryllium bonds are present in those systems. In order to know if these changes on the chemical properties could be considered a general behavior of carboxylic acids upon complexation with beryllium compounds, complexes between a set of representative carboxylic acids RCOOH (formic acid, acetic acid, propanoic acid, benzoic acid, and oxalic acid) and beryllium compounds BeX2 (X = H, F, Cl) were studied by means of density functional theory calculations. Complexes that contain a dihydrogen bond or a OH···X interaction are the most stable in comparison with other possible BeX2 complexation patterns in which no other weak interactions are involved apart from the beryllium bond. Formic, acetic, propanoic, benzoic, and oxalic acid complexes with BeX2 are much stronger acids than their related free forms. The analysis of the topology of the electron density helps to clarify the reasons behind this acidity enhancement. Importantly, when the halogen atom is replaced by hydrogen in the beryllium compound, the dihydrogen bond complex spontaneously generates a new neutral complex [RCOO:BeH] in which a hydrogen molecule is lost. This seems to be a trend for carboxylic acids on complexing BeX2 compounds.
authors.affiliation: Departamento de Química, Facultad de Ciencias, Módulo 13 Universidad Autónoma de Madrid Campus de Excelencia UAM-CSIC , Cantoblanco, 28049 Madrid, Spain.
authors.forename: Kateryna
authors.initials: K
authors.lastname: Mykolayivna-Lemishko
authors.forename: M Merced
authors.initials: MM
authors.lastname: Montero-Campillo
authors.forename: Otilia
authors.initials: O
authors.lastname: Mó
authors.forename: Manuel
authors.initials: M
authors.lastname: Yáñez
mesh_terms: D001608:Beryllium / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry*; D003198:Computer Simulation; D004583:Electrons; D005459:Fluorides / Q000737:chemistry*; D005740:Gases / Q000737:chemistry; D006859:Hydrogen / Q000737:chemistry; D008956:Models, Chemical; D011522:Protons
chemical_list: D002264:Carboxylic Acids; D005740:Gases; D011522:Protons; C035982:beryllium fluoride; C032776:beryllium chloride; D006859:Hydrogen; D001608:Beryllium; D005459:Fluorides