Hydrogen bonding and protonation effects in amino acids' anthraquinone derivatives - spectroscopic and electrochemical studies
Sandra Ramotowska , Dorota Zarzeczańska , Iwona Dąbkowska , Anna Wcisło , Paweł Niedziałkowski , Elżbieta Czaczyk , Beata Grobelna , Tadeusz Ossowski
AbstractSix novel amino acid chromophores were synthesized and their spectroscopic, acid-base, and electrochemical properties are discussed in this work. In studied compounds, selected amino acid residues (L-Aspartic acid, LGlutamic acid, L-Glutamine, L-Histidine, L-Lysine, L-Arginine) are attached to the 1-(piperazine) 9,10-anthraquinone skeleton via the amide bond between the carboxyl group of amino acid and nitrogen atomof the piperazine ring. All derivatives have been characterized using a variety of spectroscopic techniques (mass spectrometry, 1HNMR, UV–Vis, IR spectroscopy), acid-base (electrochemical and UV–Vis) titrations, and cyclic voltammetry methods. Basing on observed experimental effects, supported by quantum chemical simulations, the structureproperties links were established. They are indicative of the specific interactions within and/or in-between amino acid side groups,which are prone to formboth, intra- and intermolecular hydrogen bonds aswell as electrostatic interactions with the anthraquinone system.
|Journal series||Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, ISSN 1386-1425, (N/A 100 pkt)|
|Publication size in sheets||0.5|
|Keywords in English||Anthraquinone, amino acids, pyroglutamic acid, hydrogen bonding, protonation, electrochemistry|
|ASJC Classification||; ; ;|
|Score||= 100.0, 28-01-2020, ArticleFromJournal|
|Publication indicators||= 0; : 2017 = 1.104; : 2018 = 2.931 (2) - 2018=2.665 (5)|
|Citation count*||1 (2020-01-29)|
* presented citation count is obtained through Internet information analysis and it is close to the number calculated by the Publish or Perish system.