Unexpectedly High Acidity of Water-Soluble Phosphacoumarins

Описание

Тип публикации: статья из журнала

Год издания: 2025

Идентификатор DOI: 10.3390/chemistry7060175

Аннотация: <jats:p>In this work, we report the one-pot synthesis and characterization of four water-soluble 2-hydroxybenzo[e][1,2]oxaphosphinine 2-oxides. The compounds were obtained by cascade reactions of (2-ethoxyvinyl)phosphonic dichloride with phenol or naphthol derivatives, and their acid–base, structural, and photophysical properties wПоказать полностьюere investigated using a combination of experimental and computational methods. These compounds exhibit UV–vis absorption maxima at 209–341 nm and fluorescence maxima at 300–394 nm. Notably, these cyclic phosphonic acids exhibit unusually strong acidity with pKa values from −1.3 to 0, comparable to mineral acids; complete protonation is not achieved even in concentrated HCl. The acidity trends and spectra were further analyzed by DFT using both explicit and implicit solvation models.</jats:p>

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Издание

Журнал: Chemistry

Выпуск журнала: Т. 7, 6

Номера страниц: 175

ISSN журнала: 26248549

Место издания: Basel

Издатель: MDPI

Персоны

  • Ivanenko Timur Yu. (Siberian Federal University)
  • Zalaltdinova Alena V. (Arbuzov Institute of Organic and Physical Chemistry, Federal Research Center «Kazan Scientific Center», Russian Academy of Science)
  • Darmagambet Klara Kh. (Laboratory of Engineering Profile “Physical and Chemical Methods of Analysis”, Korkyt Ata Kyzylorda University)
  • Gerasimova Marina A. (Siberian Federal University)
  • Sadykova Yulia M. (Arbuzov Institute of Organic and Physical Chemistry, Federal Research Center «Kazan Scientific Center», Russian Academy of Science)
  • Levandovski Valeriy D. (Siberian Federal University)
  • Gazizov Almir S. (Arbuzov Institute of Organic and Physical Chemistry, Federal Research Center «Kazan Scientific Center», Russian Academy of Science)
  • Akylbekov Nurgali I. (Laboratory of Engineering Profile “Physical and Chemical Methods of Analysis”, Korkyt Ata Kyzylorda University)
  • Appazov Nurbol O. (Laboratory of Engineering Profile “Physical and Chemical Methods of Analysis”, Korkyt Ata Kyzylorda University)
  • Burilov Alexander R. (Arbuzov Institute of Organic and Physical Chemistry, Federal Research Center «Kazan Scientific Center», Russian Academy of Science)
  • Lutoshkin Maxim A. (Federal Research Center «Krasnoyarsk Science Center of the Siberian Branch of the Russian Academy of Science»)

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