A comparative study of the linear solvation energy relationship for the reactivity of pyridine carboxylic acids with diazodiphenylmethane in protic and aprotic solvents
Komparativna studija linearne korelacije slobodnih energija za reaktivnost piridin-karboksilnih kiselina sa diazodifenil-metanom u protičnim i aprotičnim rastvaračima
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The effects of protic and aprotic solvents on the reactivity of picolinic, nicotinic and isonicotinic acid, as well as of some substituted nicotinic acids, with diazodiphenylmethane (DDM) were investigated. In order to explain the kinetic results through solvent effects, the second-order rate constants for the reaction of the examined acids with DDM were correlated using the Camlet-Taft Solvatochromic Equation. The correlations of the kinetic data were realized by means of multiple linear regression analysis and the solvent effects on the reaction rates were analyzed in terms of the contributions of the initial and the transition state. The signs of the coefficients of the Equation support the already known reaction mechanism. Solvation models for all the investigated acids are suggested and related to their specific structure.
U ovom radu analiziran je uticaj protičnih i aprotičnih rastvarača na reaktivnost pikolinske, nikotinske i izonikotinske kiseline, kao i nekoliko supstituisanih nikotinskih kiselina sa diazodifenilmetanom (DDM). Da bi se dobijeni kinetički podaci mogli objasniti pomoću efekata rastvarača, konstante drugog reda za reakciju ispitivanih kiselina i DDM-a su korelisane Kamlet-Taftovom totalnom solvatohromnom jednačinom. Korelacija kinetičkih podataka urađena je višestrukom linearnom regresionom analizom i efekat rastvarača je posmatran sa strane osnovnog stanja, odnosno reaktanata, i prelaznog stanja u reakciji. Aritmetički znaci ispred koeficijenata u jednačini su u skladu sa poznatim mehanizmom ispitivane reakcije. Solvatacioni modeli za sve ispitivane kiseline su predloženi i povezani sa specifičnostima njihovih struktura.
Кључне речи:
pyridine carboxylic acids / linear solvation energy relationship / diazodiphenylmethane / protic and aprotic solventsИзвор:
Journal of the Serbian Chemical Society, 2012, 77, 10, 1311-1338Издавач:
- Serbian Chemical Society, Belgrade
Финансирање / пројекти:
- Проучавање синтезе, структуре и активности органских једињења природног и синтетског порекла (RS-MESTD-Basic Research (BR or ON)-172013)
Институција/група
Tehnološko-metalurški fakultetTY - JOUR AU - Drmanić, Saša AU - Nikolić, Jasmina AU - Marinković, Aleksandar AU - Jovanović, Bratislav Ž. PY - 2012 UR - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/2073 AB - The effects of protic and aprotic solvents on the reactivity of picolinic, nicotinic and isonicotinic acid, as well as of some substituted nicotinic acids, with diazodiphenylmethane (DDM) were investigated. In order to explain the kinetic results through solvent effects, the second-order rate constants for the reaction of the examined acids with DDM were correlated using the Camlet-Taft Solvatochromic Equation. The correlations of the kinetic data were realized by means of multiple linear regression analysis and the solvent effects on the reaction rates were analyzed in terms of the contributions of the initial and the transition state. The signs of the coefficients of the Equation support the already known reaction mechanism. Solvation models for all the investigated acids are suggested and related to their specific structure. AB - U ovom radu analiziran je uticaj protičnih i aprotičnih rastvarača na reaktivnost pikolinske, nikotinske i izonikotinske kiseline, kao i nekoliko supstituisanih nikotinskih kiselina sa diazodifenilmetanom (DDM). Da bi se dobijeni kinetički podaci mogli objasniti pomoću efekata rastvarača, konstante drugog reda za reakciju ispitivanih kiselina i DDM-a su korelisane Kamlet-Taftovom totalnom solvatohromnom jednačinom. Korelacija kinetičkih podataka urađena je višestrukom linearnom regresionom analizom i efekat rastvarača je posmatran sa strane osnovnog stanja, odnosno reaktanata, i prelaznog stanja u reakciji. Aritmetički znaci ispred koeficijenata u jednačini su u skladu sa poznatim mehanizmom ispitivane reakcije. Solvatacioni modeli za sve ispitivane kiseline su predloženi i povezani sa specifičnostima njihovih struktura. PB - Serbian Chemical Society, Belgrade T2 - Journal of the Serbian Chemical Society T1 - A comparative study of the linear solvation energy relationship for the reactivity of pyridine carboxylic acids with diazodiphenylmethane in protic and aprotic solvents T1 - Komparativna studija linearne korelacije slobodnih energija za reaktivnost piridin-karboksilnih kiselina sa diazodifenil-metanom u protičnim i aprotičnim rastvaračima EP - 1338 IS - 10 SP - 1311 VL - 77 UR - https://hdl.handle.net/21.15107/rcub_technorep_2073 ER -
@article{ author = "Drmanić, Saša and Nikolić, Jasmina and Marinković, Aleksandar and Jovanović, Bratislav Ž.", year = "2012", abstract = "The effects of protic and aprotic solvents on the reactivity of picolinic, nicotinic and isonicotinic acid, as well as of some substituted nicotinic acids, with diazodiphenylmethane (DDM) were investigated. In order to explain the kinetic results through solvent effects, the second-order rate constants for the reaction of the examined acids with DDM were correlated using the Camlet-Taft Solvatochromic Equation. The correlations of the kinetic data were realized by means of multiple linear regression analysis and the solvent effects on the reaction rates were analyzed in terms of the contributions of the initial and the transition state. The signs of the coefficients of the Equation support the already known reaction mechanism. Solvation models for all the investigated acids are suggested and related to their specific structure., U ovom radu analiziran je uticaj protičnih i aprotičnih rastvarača na reaktivnost pikolinske, nikotinske i izonikotinske kiseline, kao i nekoliko supstituisanih nikotinskih kiselina sa diazodifenilmetanom (DDM). Da bi se dobijeni kinetički podaci mogli objasniti pomoću efekata rastvarača, konstante drugog reda za reakciju ispitivanih kiselina i DDM-a su korelisane Kamlet-Taftovom totalnom solvatohromnom jednačinom. Korelacija kinetičkih podataka urađena je višestrukom linearnom regresionom analizom i efekat rastvarača je posmatran sa strane osnovnog stanja, odnosno reaktanata, i prelaznog stanja u reakciji. Aritmetički znaci ispred koeficijenata u jednačini su u skladu sa poznatim mehanizmom ispitivane reakcije. Solvatacioni modeli za sve ispitivane kiseline su predloženi i povezani sa specifičnostima njihovih struktura.", publisher = "Serbian Chemical Society, Belgrade", journal = "Journal of the Serbian Chemical Society", title = "A comparative study of the linear solvation energy relationship for the reactivity of pyridine carboxylic acids with diazodiphenylmethane in protic and aprotic solvents, Komparativna studija linearne korelacije slobodnih energija za reaktivnost piridin-karboksilnih kiselina sa diazodifenil-metanom u protičnim i aprotičnim rastvaračima", pages = "1338-1311", number = "10", volume = "77", url = "https://hdl.handle.net/21.15107/rcub_technorep_2073" }
Drmanić, S., Nikolić, J., Marinković, A.,& Jovanović, B. Ž.. (2012). A comparative study of the linear solvation energy relationship for the reactivity of pyridine carboxylic acids with diazodiphenylmethane in protic and aprotic solvents. in Journal of the Serbian Chemical Society Serbian Chemical Society, Belgrade., 77(10), 1311-1338. https://hdl.handle.net/21.15107/rcub_technorep_2073
Drmanić S, Nikolić J, Marinković A, Jovanović BŽ. A comparative study of the linear solvation energy relationship for the reactivity of pyridine carboxylic acids with diazodiphenylmethane in protic and aprotic solvents. in Journal of the Serbian Chemical Society. 2012;77(10):1311-1338. https://hdl.handle.net/21.15107/rcub_technorep_2073 .
Drmanić, Saša, Nikolić, Jasmina, Marinković, Aleksandar, Jovanović, Bratislav Ž., "A comparative study of the linear solvation energy relationship for the reactivity of pyridine carboxylic acids with diazodiphenylmethane in protic and aprotic solvents" in Journal of the Serbian Chemical Society, 77, no. 10 (2012):1311-1338, https://hdl.handle.net/21.15107/rcub_technorep_2073 .