pK a Determination of Newly Synthesized N‑(benzothiazole-2-yl)-2-(4,5-dimethyl-1-(phenylamino)-1H-imidazol-2-ylthio)acetamide Derivatives

In this work, nine drug precursors, 2-(4,5-dimethyl-1-(phenylamino)-1H-imidazol-2-ylthio)-N-(benzothiazole-2-yl) acetamide derivative compounds, were newly synthesized by reacting 4,5-dimethyl-1-(phenylamino)-1H-imidazole-2(3H)-thione derivatives with 2-chloro-N-(thiazol-2-yl) acetamide compounds. S...

Full description

Saved in:
Bibliographic Details
Published in:Industrial & engineering chemistry research 2013-06, Vol.52 (25), p.8355-8360
Main Authors: Duran, Murat, Canbaz, Mehmet Çetin
Format: Article
Language:English
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
cited_by
cites
container_end_page 8360
container_issue 25
container_start_page 8355
container_title Industrial & engineering chemistry research
container_volume 52
creator Duran, Murat
Canbaz, Mehmet Çetin
description In this work, nine drug precursors, 2-(4,5-dimethyl-1-(phenylamino)-1H-imidazol-2-ylthio)-N-(benzothiazole-2-yl) acetamide derivative compounds, were newly synthesized by reacting 4,5-dimethyl-1-(phenylamino)-1H-imidazole-2(3H)-thione derivatives with 2-chloro-N-(thiazol-2-yl) acetamide compounds. Structures of the synthesized compounds were confirmed by 1H NMR, FTIR (Fourier transform infrared), MS (mass spectroscopy), and elemental analysis. The acidity constants of these acetamide derivatives were determined via UV spectroscopic studies. It was found that the first protonation of these compounds occurs on the nitrogen at imidazole ring, while the second protonation of these compounds occurs on the nitrogen at benzothiazole ring. The first pK a values were found to vary between 5.91 and 8.34 while the second pK a values were varying between 3.02 and 4.72.
doi_str_mv 10.1021/ie400316r
format article
fullrecord <record><control><sourceid>acs</sourceid><recordid>TN_cdi_acs_journals_10_1021_ie400316r</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>b85355947</sourcerecordid><originalsourceid>FETCH-LOGICAL-a115t-62dad5f77c392c72e60a8b3609112429125bcdad9d55088cae155122f98f85e03</originalsourceid><addsrcrecordid>eNo9kD9PwzAQxS0EEqUw8A2yIDUSBp-TS50RlT9FVGUA5shNLoqrNK4SU5RO7Ex8RT4JLiCWu-Hu957eY-wUxAUICZeGYiEiSNo9NgCUgqOIcZ8NhFKKo1J4yI66bimEQIzjAftYPwQ6uCZH7co02hnbBLYM5vRW98FT37iKOrOlIph_vX-OFtRsrauM3tqauOR9Hfo5is-RF2ZFruprDny0rqjpa-0Fbchhys3KFDvkh_C4DXVOzt8L8tat2XjfDXXH7KDUdUcnf3vIXm5vnidTPnu8u59czbgGQMcTWegCy_E4j1KZjyUlQqtFlIgUQMYyBYmL3L-kBaKPnWsCRJCyTFWpkEQ0ZGe_ujrvsqV9bRvvloHIdg1m_w1G3zKxZB4</addsrcrecordid><sourcetype>Publisher</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>pK a Determination of Newly Synthesized N‑(benzothiazole-2-yl)-2-(4,5-dimethyl-1-(phenylamino)-1H-imidazol-2-ylthio)acetamide Derivatives</title><source>American Chemical Society:Jisc Collections:American Chemical Society Read &amp; Publish Agreement 2022-2024 (Reading list)</source><creator>Duran, Murat ; Canbaz, Mehmet Çetin</creator><creatorcontrib>Duran, Murat ; Canbaz, Mehmet Çetin</creatorcontrib><description>In this work, nine drug precursors, 2-(4,5-dimethyl-1-(phenylamino)-1H-imidazol-2-ylthio)-N-(benzothiazole-2-yl) acetamide derivative compounds, were newly synthesized by reacting 4,5-dimethyl-1-(phenylamino)-1H-imidazole-2(3H)-thione derivatives with 2-chloro-N-(thiazol-2-yl) acetamide compounds. Structures of the synthesized compounds were confirmed by 1H NMR, FTIR (Fourier transform infrared), MS (mass spectroscopy), and elemental analysis. The acidity constants of these acetamide derivatives were determined via UV spectroscopic studies. It was found that the first protonation of these compounds occurs on the nitrogen at imidazole ring, while the second protonation of these compounds occurs on the nitrogen at benzothiazole ring. The first pK a values were found to vary between 5.91 and 8.34 while the second pK a values were varying between 3.02 and 4.72.</description><identifier>ISSN: 0888-5885</identifier><identifier>EISSN: 1520-5045</identifier><identifier>DOI: 10.1021/ie400316r</identifier><language>eng</language><publisher>American Chemical Society</publisher><ispartof>Industrial &amp; engineering chemistry research, 2013-06, Vol.52 (25), p.8355-8360</ispartof><rights>Copyright © 2013 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids></links><search><creatorcontrib>Duran, Murat</creatorcontrib><creatorcontrib>Canbaz, Mehmet Çetin</creatorcontrib><title>pK a Determination of Newly Synthesized N‑(benzothiazole-2-yl)-2-(4,5-dimethyl-1-(phenylamino)-1H-imidazol-2-ylthio)acetamide Derivatives</title><title>Industrial &amp; engineering chemistry research</title><addtitle>Ind. Eng. Chem. Res</addtitle><description>In this work, nine drug precursors, 2-(4,5-dimethyl-1-(phenylamino)-1H-imidazol-2-ylthio)-N-(benzothiazole-2-yl) acetamide derivative compounds, were newly synthesized by reacting 4,5-dimethyl-1-(phenylamino)-1H-imidazole-2(3H)-thione derivatives with 2-chloro-N-(thiazol-2-yl) acetamide compounds. Structures of the synthesized compounds were confirmed by 1H NMR, FTIR (Fourier transform infrared), MS (mass spectroscopy), and elemental analysis. The acidity constants of these acetamide derivatives were determined via UV spectroscopic studies. It was found that the first protonation of these compounds occurs on the nitrogen at imidazole ring, while the second protonation of these compounds occurs on the nitrogen at benzothiazole ring. The first pK a values were found to vary between 5.91 and 8.34 while the second pK a values were varying between 3.02 and 4.72.</description><issn>0888-5885</issn><issn>1520-5045</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><sourceid/><recordid>eNo9kD9PwzAQxS0EEqUw8A2yIDUSBp-TS50RlT9FVGUA5shNLoqrNK4SU5RO7Ex8RT4JLiCWu-Hu957eY-wUxAUICZeGYiEiSNo9NgCUgqOIcZ8NhFKKo1J4yI66bimEQIzjAftYPwQ6uCZH7co02hnbBLYM5vRW98FT37iKOrOlIph_vX-OFtRsrauM3tqauOR9Hfo5is-RF2ZFruprDny0rqjpa-0Fbchhys3KFDvkh_C4DXVOzt8L8tat2XjfDXXH7KDUdUcnf3vIXm5vnidTPnu8u59czbgGQMcTWegCy_E4j1KZjyUlQqtFlIgUQMYyBYmL3L-kBaKPnWsCRJCyTFWpkEQ0ZGe_ujrvsqV9bRvvloHIdg1m_w1G3zKxZB4</recordid><startdate>20130626</startdate><enddate>20130626</enddate><creator>Duran, Murat</creator><creator>Canbaz, Mehmet Çetin</creator><general>American Chemical Society</general><scope/></search><sort><creationdate>20130626</creationdate><title>pK a Determination of Newly Synthesized N‑(benzothiazole-2-yl)-2-(4,5-dimethyl-1-(phenylamino)-1H-imidazol-2-ylthio)acetamide Derivatives</title><author>Duran, Murat ; Canbaz, Mehmet Çetin</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a115t-62dad5f77c392c72e60a8b3609112429125bcdad9d55088cae155122f98f85e03</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Duran, Murat</creatorcontrib><creatorcontrib>Canbaz, Mehmet Çetin</creatorcontrib><jtitle>Industrial &amp; engineering chemistry research</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Duran, Murat</au><au>Canbaz, Mehmet Çetin</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>pK a Determination of Newly Synthesized N‑(benzothiazole-2-yl)-2-(4,5-dimethyl-1-(phenylamino)-1H-imidazol-2-ylthio)acetamide Derivatives</atitle><jtitle>Industrial &amp; engineering chemistry research</jtitle><addtitle>Ind. Eng. Chem. Res</addtitle><date>2013-06-26</date><risdate>2013</risdate><volume>52</volume><issue>25</issue><spage>8355</spage><epage>8360</epage><pages>8355-8360</pages><issn>0888-5885</issn><eissn>1520-5045</eissn><abstract>In this work, nine drug precursors, 2-(4,5-dimethyl-1-(phenylamino)-1H-imidazol-2-ylthio)-N-(benzothiazole-2-yl) acetamide derivative compounds, were newly synthesized by reacting 4,5-dimethyl-1-(phenylamino)-1H-imidazole-2(3H)-thione derivatives with 2-chloro-N-(thiazol-2-yl) acetamide compounds. Structures of the synthesized compounds were confirmed by 1H NMR, FTIR (Fourier transform infrared), MS (mass spectroscopy), and elemental analysis. The acidity constants of these acetamide derivatives were determined via UV spectroscopic studies. It was found that the first protonation of these compounds occurs on the nitrogen at imidazole ring, while the second protonation of these compounds occurs on the nitrogen at benzothiazole ring. The first pK a values were found to vary between 5.91 and 8.34 while the second pK a values were varying between 3.02 and 4.72.</abstract><pub>American Chemical Society</pub><doi>10.1021/ie400316r</doi><tpages>6</tpages></addata></record>
fulltext fulltext
identifier ISSN: 0888-5885
ispartof Industrial & engineering chemistry research, 2013-06, Vol.52 (25), p.8355-8360
issn 0888-5885
1520-5045
language eng
recordid cdi_acs_journals_10_1021_ie400316r
source American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
title pK a Determination of Newly Synthesized N‑(benzothiazole-2-yl)-2-(4,5-dimethyl-1-(phenylamino)-1H-imidazol-2-ylthio)acetamide Derivatives
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-07T15%3A27%3A25IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-acs&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=pK%20a%20Determination%20of%20Newly%20Synthesized%20N%E2%80%91(benzothiazole-2-yl)-2-(4,5-dimethyl-1-(phenylamino)-1H-imidazol-2-ylthio)acetamide%20Derivatives&rft.jtitle=Industrial%20&%20engineering%20chemistry%20research&rft.au=Duran,%20Murat&rft.date=2013-06-26&rft.volume=52&rft.issue=25&rft.spage=8355&rft.epage=8360&rft.pages=8355-8360&rft.issn=0888-5885&rft.eissn=1520-5045&rft_id=info:doi/10.1021/ie400316r&rft_dat=%3Cacs%3Eb85355947%3C/acs%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-a115t-62dad5f77c392c72e60a8b3609112429125bcdad9d55088cae155122f98f85e03%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_id=info:pmid/&rfr_iscdi=true