Nucleophilicity and solvent effects on the kinetics of 4-(pyren-1-yl)thiazol-2-amine interaction with 4,6-dinitrobenzofuroxan
A multistep synthesis of novel pyrene-based thiazole moiety been has been realized following some synthetic challenges and complications. The chemical structure of the synthesized compound has been established on the basis of both spectroscopic and analytical tools. Its nucleophilic reactivity with...
| Main Authors: | , , , , , , , , , , |
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| Format: | Article |
| Language: | English |
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Elsevier
2020-02-01
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| Series: | Arabian Journal of Chemistry |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S1878535220300034 |
| _version_ | 1811325070187954176 |
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| author | Nizar El Guesmi Essam M. Hussein Basim H. Asghar Rami J. Obaid Rabab S. Jassas Ahmed Alharbi Hatem M. Altass Ismail I. Althagafi Moataz Morad Ziad Moussa Saleh A. Ahmed |
| author_facet | Nizar El Guesmi Essam M. Hussein Basim H. Asghar Rami J. Obaid Rabab S. Jassas Ahmed Alharbi Hatem M. Altass Ismail I. Althagafi Moataz Morad Ziad Moussa Saleh A. Ahmed |
| author_sort | Nizar El Guesmi |
| collection | DOAJ |
| description | A multistep synthesis of novel pyrene-based thiazole moiety been has been realized following some synthetic challenges and complications. The chemical structure of the synthesized compound has been established on the basis of both spectroscopic and analytical tools. Its nucleophilic reactivity with 4,6-dinitrobenzofuroxan (DNBF) has been successfully studied in solution. A kinetic study of the covalent electrophile/nucleophile combination of dinitrobenzofuroxan (DNBF, electrophile) and 4-(pyren-1-yl)thiazol-2-amine (nucleophile) resulting in the formation of the corresponding σ-adduct in solution is reported. The rate constant (k1) of the second-order relating to the CC bond forming step of this complexation process has been found to fit into the linear correlation log k = sN (N + E), thereby permitting the evaluation of the nucleophilicity parameter (N) of the 4-(pyren-1-yl)thiazol-2-amine. 4-(Pyren-1-yl)thiazol-2-amine has been subsequently ranked according to its reactivity profile on the general nucleophilicity scale developed recently by Mayr et al., leading to an interesting and direct comparison over a large domain of π-, σ-, and n-nucleophiles. Keywords: Pyrene-based heterocycles, Nucleophilicity parameters, Dinitrobenzofuroxan, Kinetic study |
| first_indexed | 2024-04-13T14:26:33Z |
| format | Article |
| id | doaj.art-a1db03192559478c93543e1728ea6886 |
| institution | Directory Open Access Journal |
| issn | 1878-5352 |
| language | English |
| last_indexed | 2024-04-13T14:26:33Z |
| publishDate | 2020-02-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Arabian Journal of Chemistry |
| spelling | doaj.art-a1db03192559478c93543e1728ea68862022-12-22T02:43:19ZengElsevierArabian Journal of Chemistry1878-53522020-02-0113237023713Nucleophilicity and solvent effects on the kinetics of 4-(pyren-1-yl)thiazol-2-amine interaction with 4,6-dinitrobenzofuroxanNizar El Guesmi0Essam M. Hussein1Basim H. Asghar2Rami J. Obaid3Rabab S. Jassas4Ahmed Alharbi5Hatem M. Altass6Ismail I. Althagafi7Moataz Morad8Ziad Moussa9Saleh A. Ahmed10Department of Chemistry, Faculty of Applied Science, Umm Al-Qura University, 21955 Makkah, Saudi Arabia; Département de Chimie, Faculté des Sciences de Monastir, Avenue de l’Environnement, 5019 Monastir, TunisiaDepartment of Chemistry, Faculty of Applied Science, Umm Al-Qura University, 21955 Makkah, Saudi Arabia; Department of Chemistry, Faculty of Science, Assiut University, 71516 Assiut, EgyptDepartment of Chemistry, Faculty of Applied Science, Umm Al-Qura University, 21955 Makkah, Saudi ArabiaDepartment of Chemistry, Faculty of Applied Science, Umm Al-Qura University, 21955 Makkah, Saudi ArabiaDepartment of Chemistry, Jamoum University College, Umm Al-Qura University, 21955 Makkah, Saudi ArabiaDepartment of Chemistry, Faculty of Applied Science, Umm Al-Qura University, 21955 Makkah, Saudi ArabiaDepartment of Chemistry, Faculty of Applied Science, Umm Al-Qura University, 21955 Makkah, Saudi ArabiaDepartment of Chemistry, Faculty of Applied Science, Umm Al-Qura University, 21955 Makkah, Saudi ArabiaDepartment of Chemistry, Faculty of Applied Science, Umm Al-Qura University, 21955 Makkah, Saudi ArabiaDepartment of Chemistry, College of Science, United Arab Emirates University, P.O. Box 15551, Al Ain, Abu Dhabi, United Arab EmiratesDepartment of Chemistry, Faculty of Applied Science, Umm Al-Qura University, 21955 Makkah, Saudi Arabia; Department of Chemistry, Faculty of Science, Assiut University, 71516 Assiut, Egypt; Corresponding author at: Department of Chemistry, Faculty of Applied Science, Umm Al-Qura University, 21955 Makkah, Saudi Arabia. Tel./Fax: +966 530435760.A multistep synthesis of novel pyrene-based thiazole moiety been has been realized following some synthetic challenges and complications. The chemical structure of the synthesized compound has been established on the basis of both spectroscopic and analytical tools. Its nucleophilic reactivity with 4,6-dinitrobenzofuroxan (DNBF) has been successfully studied in solution. A kinetic study of the covalent electrophile/nucleophile combination of dinitrobenzofuroxan (DNBF, electrophile) and 4-(pyren-1-yl)thiazol-2-amine (nucleophile) resulting in the formation of the corresponding σ-adduct in solution is reported. The rate constant (k1) of the second-order relating to the CC bond forming step of this complexation process has been found to fit into the linear correlation log k = sN (N + E), thereby permitting the evaluation of the nucleophilicity parameter (N) of the 4-(pyren-1-yl)thiazol-2-amine. 4-(Pyren-1-yl)thiazol-2-amine has been subsequently ranked according to its reactivity profile on the general nucleophilicity scale developed recently by Mayr et al., leading to an interesting and direct comparison over a large domain of π-, σ-, and n-nucleophiles. Keywords: Pyrene-based heterocycles, Nucleophilicity parameters, Dinitrobenzofuroxan, Kinetic studyhttp://www.sciencedirect.com/science/article/pii/S1878535220300034 |
| spellingShingle | Nizar El Guesmi Essam M. Hussein Basim H. Asghar Rami J. Obaid Rabab S. Jassas Ahmed Alharbi Hatem M. Altass Ismail I. Althagafi Moataz Morad Ziad Moussa Saleh A. Ahmed Nucleophilicity and solvent effects on the kinetics of 4-(pyren-1-yl)thiazol-2-amine interaction with 4,6-dinitrobenzofuroxan Arabian Journal of Chemistry |
| title | Nucleophilicity and solvent effects on the kinetics of 4-(pyren-1-yl)thiazol-2-amine interaction with 4,6-dinitrobenzofuroxan |
| title_full | Nucleophilicity and solvent effects on the kinetics of 4-(pyren-1-yl)thiazol-2-amine interaction with 4,6-dinitrobenzofuroxan |
| title_fullStr | Nucleophilicity and solvent effects on the kinetics of 4-(pyren-1-yl)thiazol-2-amine interaction with 4,6-dinitrobenzofuroxan |
| title_full_unstemmed | Nucleophilicity and solvent effects on the kinetics of 4-(pyren-1-yl)thiazol-2-amine interaction with 4,6-dinitrobenzofuroxan |
| title_short | Nucleophilicity and solvent effects on the kinetics of 4-(pyren-1-yl)thiazol-2-amine interaction with 4,6-dinitrobenzofuroxan |
| title_sort | nucleophilicity and solvent effects on the kinetics of 4 pyren 1 yl thiazol 2 amine interaction with 4 6 dinitrobenzofuroxan |
| url | http://www.sciencedirect.com/science/article/pii/S1878535220300034 |
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