Investigations of the reactivity of pyridine carboxylic acids with diazodiphenylmethane in protic and aprotic solvents: Part II: Pyridine mono-carboxylic acid N-oxides
Ispitivanje reaktivnosti piridin-N-oksid-monokarbonskih kiselina u reakciji sa diazodifenilmetanom u protičnim i aprotičnim rastvaračima - drugi deo
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The rate constants for the reaction of three isomeric pyridine mono-carbocylic acid N-oxides with diazodiphenylmethane were determined at 30 ºC in thirty two protic and aprotic solvents by the well known UV spectrophotometric method. The rate constants are generally higher than for pyridine mono-carboxylic acids in a similar range of solvents, except for picolinic acid N-oxide, and also higher in protic than in aprotic solvents. The determined rate constants were correlated with solvent parameters using the Kamlet-Taft solvatochromic equation bymeans of multiple regression analysis. The sign of the equation coefficients were in agreement with the postulated reaction mechanism. The mode of the influences of the solvent is discussed on the basis of the correlation coefficients, taking into account the specific structures of the pyridine mono-carboxylic acid N-oxides.
Konstante brzina reakcije između diazodifenilmetana i izomernih piridin-N-oksidkarbonskih kiselina određene u trideset dva protična i aprotična rastvarača na 30 ºC, korišćenjem poznate UV spektrofotometrijske metode, analizirane su u funkciji efekata rastvarača. Vrednosti konstanti brzina su generalno veće za piridin-N-oksid- karbonske kiseline u odnosu na piridin-monokarbonske kiseline, izuzev pikolin-N-oksid-kiseline, a takođe vrednosti konstanti brzina su veće u protičnim rastvarač ima u poređenju sa aprotičnim za obe serije kiselina. Određene konstante brzina su korelisane sa parametrima rastvarača korišćenjem Kamlet-Taft solvatohromne jednačine izvedene metodom višestruke regresione analize. Znak koeficijenata u dobijenim korelacijama je u saglasnosti sa pretpostavljenim reakcionim mehanizmom. Uticaj rastvarača na vrednosti reakcionih konstanti je diskutovan na osnovu dobijenih korelacionih rezultata, uzimajući u obzir specifičnu strukturu piridin- N-oksid-monokarbonskih kiselina.
Keywords:
pyridine carboxylic acids / pyridine carboxylic acid N-oxides / diazodiphenylmethane / rate constants / solvent parameters / protic and aprotic solventsSource:
Journal of the Serbian Chemical Society, 2006, 71, 2, 89-101Publisher:
- Serbian Chemical Society, Belgrade
Institution/Community
Tehnološko-metalurški fakultetTY - JOUR AU - Drmanić, Saša AU - Jovanović, Bratislav Ž. AU - Marinković, Aleksandar AU - Misić-Vuković, Milica PY - 2006 UR - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/994 AB - The rate constants for the reaction of three isomeric pyridine mono-carbocylic acid N-oxides with diazodiphenylmethane were determined at 30 ºC in thirty two protic and aprotic solvents by the well known UV spectrophotometric method. The rate constants are generally higher than for pyridine mono-carboxylic acids in a similar range of solvents, except for picolinic acid N-oxide, and also higher in protic than in aprotic solvents. The determined rate constants were correlated with solvent parameters using the Kamlet-Taft solvatochromic equation bymeans of multiple regression analysis. The sign of the equation coefficients were in agreement with the postulated reaction mechanism. The mode of the influences of the solvent is discussed on the basis of the correlation coefficients, taking into account the specific structures of the pyridine mono-carboxylic acid N-oxides. AB - Konstante brzina reakcije između diazodifenilmetana i izomernih piridin-N-oksidkarbonskih kiselina određene u trideset dva protična i aprotična rastvarača na 30 ºC, korišćenjem poznate UV spektrofotometrijske metode, analizirane su u funkciji efekata rastvarača. Vrednosti konstanti brzina su generalno veće za piridin-N-oksid- karbonske kiseline u odnosu na piridin-monokarbonske kiseline, izuzev pikolin-N-oksid-kiseline, a takođe vrednosti konstanti brzina su veće u protičnim rastvarač ima u poređenju sa aprotičnim za obe serije kiselina. Određene konstante brzina su korelisane sa parametrima rastvarača korišćenjem Kamlet-Taft solvatohromne jednačine izvedene metodom višestruke regresione analize. Znak koeficijenata u dobijenim korelacijama je u saglasnosti sa pretpostavljenim reakcionim mehanizmom. Uticaj rastvarača na vrednosti reakcionih konstanti je diskutovan na osnovu dobijenih korelacionih rezultata, uzimajući u obzir specifičnu strukturu piridin- N-oksid-monokarbonskih kiselina. PB - Serbian Chemical Society, Belgrade T2 - Journal of the Serbian Chemical Society T1 - Investigations of the reactivity of pyridine carboxylic acids with diazodiphenylmethane in protic and aprotic solvents: Part II: Pyridine mono-carboxylic acid N-oxides T1 - Ispitivanje reaktivnosti piridin-N-oksid-monokarbonskih kiselina u reakciji sa diazodifenilmetanom u protičnim i aprotičnim rastvaračima - drugi deo EP - 101 IS - 2 SP - 89 VL - 71 UR - https://hdl.handle.net/21.15107/rcub_technorep_994 ER -
@article{ author = "Drmanić, Saša and Jovanović, Bratislav Ž. and Marinković, Aleksandar and Misić-Vuković, Milica", year = "2006", abstract = "The rate constants for the reaction of three isomeric pyridine mono-carbocylic acid N-oxides with diazodiphenylmethane were determined at 30 ºC in thirty two protic and aprotic solvents by the well known UV spectrophotometric method. The rate constants are generally higher than for pyridine mono-carboxylic acids in a similar range of solvents, except for picolinic acid N-oxide, and also higher in protic than in aprotic solvents. The determined rate constants were correlated with solvent parameters using the Kamlet-Taft solvatochromic equation bymeans of multiple regression analysis. The sign of the equation coefficients were in agreement with the postulated reaction mechanism. The mode of the influences of the solvent is discussed on the basis of the correlation coefficients, taking into account the specific structures of the pyridine mono-carboxylic acid N-oxides., Konstante brzina reakcije između diazodifenilmetana i izomernih piridin-N-oksidkarbonskih kiselina određene u trideset dva protična i aprotična rastvarača na 30 ºC, korišćenjem poznate UV spektrofotometrijske metode, analizirane su u funkciji efekata rastvarača. Vrednosti konstanti brzina su generalno veće za piridin-N-oksid- karbonske kiseline u odnosu na piridin-monokarbonske kiseline, izuzev pikolin-N-oksid-kiseline, a takođe vrednosti konstanti brzina su veće u protičnim rastvarač ima u poređenju sa aprotičnim za obe serije kiselina. Određene konstante brzina su korelisane sa parametrima rastvarača korišćenjem Kamlet-Taft solvatohromne jednačine izvedene metodom višestruke regresione analize. Znak koeficijenata u dobijenim korelacijama je u saglasnosti sa pretpostavljenim reakcionim mehanizmom. Uticaj rastvarača na vrednosti reakcionih konstanti je diskutovan na osnovu dobijenih korelacionih rezultata, uzimajući u obzir specifičnu strukturu piridin- N-oksid-monokarbonskih kiselina.", publisher = "Serbian Chemical Society, Belgrade", journal = "Journal of the Serbian Chemical Society", title = "Investigations of the reactivity of pyridine carboxylic acids with diazodiphenylmethane in protic and aprotic solvents: Part II: Pyridine mono-carboxylic acid N-oxides, Ispitivanje reaktivnosti piridin-N-oksid-monokarbonskih kiselina u reakciji sa diazodifenilmetanom u protičnim i aprotičnim rastvaračima - drugi deo", pages = "101-89", number = "2", volume = "71", url = "https://hdl.handle.net/21.15107/rcub_technorep_994" }
Drmanić, S., Jovanović, B. Ž., Marinković, A.,& Misić-Vuković, M.. (2006). Investigations of the reactivity of pyridine carboxylic acids with diazodiphenylmethane in protic and aprotic solvents: Part II: Pyridine mono-carboxylic acid N-oxides. in Journal of the Serbian Chemical Society Serbian Chemical Society, Belgrade., 71(2), 89-101. https://hdl.handle.net/21.15107/rcub_technorep_994
Drmanić S, Jovanović BŽ, Marinković A, Misić-Vuković M. Investigations of the reactivity of pyridine carboxylic acids with diazodiphenylmethane in protic and aprotic solvents: Part II: Pyridine mono-carboxylic acid N-oxides. in Journal of the Serbian Chemical Society. 2006;71(2):89-101. https://hdl.handle.net/21.15107/rcub_technorep_994 .
Drmanić, Saša, Jovanović, Bratislav Ž., Marinković, Aleksandar, Misić-Vuković, Milica, "Investigations of the reactivity of pyridine carboxylic acids with diazodiphenylmethane in protic and aprotic solvents: Part II: Pyridine mono-carboxylic acid N-oxides" in Journal of the Serbian Chemical Society, 71, no. 2 (2006):89-101, https://hdl.handle.net/21.15107/rcub_technorep_994 .