Step-by-Step Replacement of Cyano Groups by Tricyanovinyls-The Influence on the Acidity

Acid-base properties are the simplest expression of compounds' coordinating ability. In the present work, we studied in silico how the gas-phase Brønsted acidity (GA) of several polycyano-substituted compounds change when cyano (CN) groups are replaced by 1,2,2-tricyanovinyl (TCNV) groups in (i...

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Published inMolecules (Basel, Switzerland) Vol. 28; no. 24; p. 8157
Main Author Kütt, Agnes
Format Journal Article
LanguageEnglish
Published Switzerland MDPI AG 01.12.2023
Subjects
Acetonitrile
acid-base properties
Comparative analysis
COSMO-RS
cyanocarbon acids
gas-phase acidity
Hydrogen
Hydrogen-ion concentration
polycyano compounds
Solvents
tricyanovinyl
polycyano compounds
acid-base properties
COSMO-RS
cyanocarbon acids
tricyanovinyl
gas-phase acidity
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Summary:Acid-base properties are the simplest expression of compounds' coordinating ability. In the present work, we studied in silico how the gas-phase Brønsted acidity (GA) of several polycyano-substituted compounds change when cyano (CN) groups are replaced by 1,2,2-tricyanovinyl (TCNV) groups in (iso)cyanic acid, dicyanoamine, cyanoform, and hydrogen tetracyanoborate. Different tautomers and conformers/isomers are included in this study. Gas-phase acidity values are compared with the acidities of various acids, including percyanated protonated monocarba- -dodecaborate (carborane acid) and dodecaborate, as well as hydrogen cyanide and 1,2,2-tricyanoethene. An estimation of acetonitrile (MeCN), dimethylsufoxide (DMSO), and 1,2-dichloroethane (DCE) acidities is presented using the COSMO-RS method and correlation analysis. The strongest acid with four TCNV groups shows remarkable acidic properties.
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ISSN:1420-3049
1420-3049
DOI:10.3390/molecules28248157