Boron-π interactions in two 3-(dihydroxyboryl)anilinium salts analyzed by crystallographic studies and supported by the noncovalent interactions (NCI) index theoretical approach.
Jacobo Rivera-Segura, Victor Barba, Iran F Hernandez-Ahuactzi, Hugo Tlahuext
{"title":"Boron-π interactions in two 3-(dihydroxyboryl)anilinium salts analyzed by crystallographic studies and supported by the noncovalent interactions (NCI) index theoretical approach.","authors":"Jacobo Rivera-Segura, Victor Barba, Iran F Hernandez-Ahuactzi, Hugo Tlahuext","doi":"10.1107/S2053229623005065","DOIUrl":null,"url":null,"abstract":"<p><p>In the title compounds, 3-(dihydroxyboryl)anilinium bisulfate monohydrate, C<sub>6</sub>H<sub>9</sub>BNO<sub>2</sub><sup>+</sup>·HSO<sub>4</sub><sup>-</sup>·H<sub>2</sub>O (I), and 3-(dihydroxyboryl)anilinium methyl sulfate, C<sub>6</sub>H<sub>9</sub>BNO<sub>2</sub><sup>+</sup>·CH<sub>3</sub>SO<sub>4</sub><sup>-</sup> (II), the almost planar boronic acid molecules are linked by pairs of O-H...O hydrogen bonds, forming centrosymmetric motifs that can be described by the graph-set R<sub>2</sub><sup>2</sup>(8) motif. In both crystals, the B(OH)<sub>2</sub> group acquires a syn-anti conformation (with respect to the H atoms). The presence of the hydrogen-bonding functional groups B(OH)<sub>2</sub>, NH<sub>3</sub><sup>+</sup>, HSO<sub>4</sub><sup>-</sup>, CH<sub>3</sub>SO<sub>4</sub><sup>-</sup> and H<sub>2</sub>O generates three-dimensional hydrogen-bonded networks, in which the bisulfate (HSO<sub>4</sub><sup>-</sup>) and methyl sulfate (CH<sub>3</sub>SO<sub>4</sub><sup>-</sup>) counter-ions act as the central building blocks within the crystal structures. Furthermore, in both structures, the packing is stabilized by weak boron-π interactions, as shown by noncovalent interactions (NCI) index calculations.</p>","PeriodicalId":7115,"journal":{"name":"Acta Crystallographica Section C Structural Chemistry","volume":null,"pages":null},"PeriodicalIF":0.7000,"publicationDate":"2023-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Acta Crystallographica Section C Structural Chemistry","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1107/S2053229623005065","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
Abstract
In the title compounds, 3-(dihydroxyboryl)anilinium bisulfate monohydrate, C6H9BNO2+·HSO4-·H2O (I), and 3-(dihydroxyboryl)anilinium methyl sulfate, C6H9BNO2+·CH3SO4- (II), the almost planar boronic acid molecules are linked by pairs of O-H...O hydrogen bonds, forming centrosymmetric motifs that can be described by the graph-set R22(8) motif. In both crystals, the B(OH)2 group acquires a syn-anti conformation (with respect to the H atoms). The presence of the hydrogen-bonding functional groups B(OH)2, NH3+, HSO4-, CH3SO4- and H2O generates three-dimensional hydrogen-bonded networks, in which the bisulfate (HSO4-) and methyl sulfate (CH3SO4-) counter-ions act as the central building blocks within the crystal structures. Furthermore, in both structures, the packing is stabilized by weak boron-π interactions, as shown by noncovalent interactions (NCI) index calculations.
期刊介绍:
Acta Crystallographica Section C: Structural Chemistry is continuing its transition to a journal that publishes exciting science with structural content, in particular, important results relating to the chemical sciences. Section C is the journal of choice for the rapid publication of articles that highlight interesting research facilitated by the determination, calculation or analysis of structures of any type, other than macromolecular structures. Articles that emphasize the science and the outcomes that were enabled by the study are particularly welcomed. Authors are encouraged to include mainstream science in their papers, thereby producing manuscripts that are substantial scientific well-rounded contributions that appeal to a broad community of readers and increase the profile of the authors.