Determination of pKa values of some benzoxazoline derivatives and the structure-activity relationship

Hayati Celik; Mahmure Büyükaǧa; Mustafa Çelebier; Ebru Turkoz Acar; Melek Sirin Baymak; Nesrin Gökhan-Kelekçi; Erhan Palaska; Hakki Erdoǧan

doi:10.1021/je3012919

Determination of pK_a values of some benzoxazoline derivatives and the structure-activity relationship

Hayati Celik
, Mahmure Büyükaǧa
, Mustafa Çelebier
, Ebru Turkoz Acar
, Melek Sirin Baymak
, Nesrin Gökhan-Kelekçi
, Erhan Palaska
, Hakki Erdoǧan

Yeditepe University
Near East University
Marmara University

Research output: Contribution to journal › Article › peer-review

11 Citations (Scopus)

Abstract

The acid ionization constant (pK_a) values of 2-(3H)-benzoxazolinone and its 17 derivatives were determined in buffered solutions by UV-vis spectrophotometry, potentiometry, and capillary zone electrophoresis techniques. The pK_a values of the studied compounds are found to be in the range of 9.01 to 7.15. The advantages and limitations of each technique are discussed. The results suggest that the removal of a proton from the molecule occurred on the nitrogen atom of the 2-(3H)-benzoxazolinone ring and the analgesic/anti-inflammatory activities of the benzoxazolinone derivatives decrease when the pK_a values of the compounds increase.

Original language	English
Pages (from-to)	1589-1596
Number of pages	8
Journal	Journal of Chemical and Engineering Data
Volume	58
Issue number	6
DOIs	https://doi.org/10.1021/je3012919
Publication status	Published - 13 Jun 2013

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10.1021/je3012919

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title = "Determination of pKa values of some benzoxazoline derivatives and the structure-activity relationship",

abstract = "The acid ionization constant (pKa) values of 2-(3H)-benzoxazolinone and its 17 derivatives were determined in buffered solutions by UV-vis spectrophotometry, potentiometry, and capillary zone electrophoresis techniques. The pKa values of the studied compounds are found to be in the range of 9.01 to 7.15. The advantages and limitations of each technique are discussed. The results suggest that the removal of a proton from the molecule occurred on the nitrogen atom of the 2-(3H)-benzoxazolinone ring and the analgesic/anti-inflammatory activities of the benzoxazolinone derivatives decrease when the pKa values of the compounds increase.",

author = "Hayati Celik and Mahmure B{\"u}y{\"u}kaǧa and Mustafa {\c C}elebier and \{Turkoz Acar\}, Ebru and Baymak, \{Melek Sirin\} and Nesrin G{\"o}khan-Kelek{\c c}i and Erhan Palaska and Hakki Erdoǧan",

year = "2013",

month = jun,

day = "13",

doi = "10.1021/je3012919",

language = "English",

volume = "58",

pages = "1589--1596",

journal = "Journal of Chemical and Engineering Data",

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TY - JOUR

T1 - Determination of pKa values of some benzoxazoline derivatives and the structure-activity relationship

AU - Celik, Hayati

AU - Büyükaǧa, Mahmure

AU - Çelebier, Mustafa

AU - Turkoz Acar, Ebru

AU - Baymak, Melek Sirin

AU - Gökhan-Kelekçi, Nesrin

AU - Palaska, Erhan

AU - Erdoǧan, Hakki

PY - 2013/6/13

Y1 - 2013/6/13

N2 - The acid ionization constant (pKa) values of 2-(3H)-benzoxazolinone and its 17 derivatives were determined in buffered solutions by UV-vis spectrophotometry, potentiometry, and capillary zone electrophoresis techniques. The pKa values of the studied compounds are found to be in the range of 9.01 to 7.15. The advantages and limitations of each technique are discussed. The results suggest that the removal of a proton from the molecule occurred on the nitrogen atom of the 2-(3H)-benzoxazolinone ring and the analgesic/anti-inflammatory activities of the benzoxazolinone derivatives decrease when the pKa values of the compounds increase.

AB - The acid ionization constant (pKa) values of 2-(3H)-benzoxazolinone and its 17 derivatives were determined in buffered solutions by UV-vis spectrophotometry, potentiometry, and capillary zone electrophoresis techniques. The pKa values of the studied compounds are found to be in the range of 9.01 to 7.15. The advantages and limitations of each technique are discussed. The results suggest that the removal of a proton from the molecule occurred on the nitrogen atom of the 2-(3H)-benzoxazolinone ring and the analgesic/anti-inflammatory activities of the benzoxazolinone derivatives decrease when the pKa values of the compounds increase.

UR - https://www.scopus.com/pages/publications/84879078204

U2 - 10.1021/je3012919

DO - 10.1021/je3012919

M3 - Article

AN - SCOPUS:84879078204

SN - 0021-9568

VL - 58

SP - 1589

EP - 1596

JO - Journal of Chemical and Engineering Data

JF - Journal of Chemical and Engineering Data

IS - 6

ER -

Determination of pK_a values of some benzoxazoline derivatives and the structure-activity relationship

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