Reactivity of cyclohex-1-enylcarboxylic and 2-methylcyclohex-1-enylcarboxylic acids with diazodiphenylmethane in aprotic solvents
Reaktivnost cikloheks-1-enilkarbonske i 2-metilcikloheks-1-enilkarbonske kiseline sa diazodifenilmetanom u aprotičnim rastvaračima
2000
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Članak u časopisu (Objavljena verzija)
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Rate constants for the reaction of diazodiphenylmethane with cyclohex-1-enylcarboxylic acid and 2-methylcyclohex-1-enylcarboxylic acid were determined in nine aprotic solvents, as well as in seven protic solvents, at 30 ºC using the appropriate UV-spectroscopic method. In protic solvents the unsubsituted acid displayed higher reaction rates than the methyl-substituted one. The results in aprotic solvents showed quite the opposite, and the reaction rates were considerably lower. In order to explain the obtained results through solvent effects, reaction rate constants (k) of the examined acids were correlated using the total solvatochromic equation of the form: log k = log k0 + sπ* + aα + bβ, where π* is the measure of the solvent polarity, α represents the scale of the solvent hydrogen bond donor acidities (HBD) and β represents the scale of the solvent hydrogen bond acceptor basicities (HBA). The correlation of the kinetic data were carried out by means of multiple linear regression an...alysis and the opposite effects of aprotic solvents, as well as the difference in the influence of protic and aprotic solvents on the reaction of the two examined acids with DDM were discussed. The results presented in this paper for cyclohex-1-enylcarboxylic and 2-methylcyclohex-1-enylcarboxylic acids were compared with the kinetic data for benzoic acid obtained in the same chemical reaction, under the same experimental conditions. .
Konstante brzine za reakciju između diazodifenilmetana (DDM) i cikloheks-1-enilkarbonske, kao i 2-methilcikloheks-1-enilkarbonske kiseline su određene u devet aprotičnih i sedam protičnih rastvarača, odgovarajućom UV-spektrofotometrijskom metodom. U protičnim rastvaračima nesupstituisana kiselina je pokazala veće reakcione brzine od supstituisane. Rezultati u aprotičnim rastvaračima su pokazali upravo suprotno i brzine su znatno manje. Da bi se dobijeni rezultati objasnili kroz efekte rastvarača, konstante brzine reakcije (k) su korelisane totalnom solvatohromnom jednačinom oblika: log k = log k0 + sπ* + aα + bβ, gde je π* mera polarnosti rastvarača, α predstavlja skalu baznosti rastvarača kao akceptora protona u vodoničnoj vezi, a β predstavlja skalu kiselosti rastvarača kao donora protona u vodoničnoj vezi. Korelacija kinetičkih podataka je izvršena metodom multiple linearne regresije i razmatrani su suprotni efekti aprotičnih rastvarača, kao i razlika u uticaju protičnih i aprotični...h rastvarača na reakciju dve ispitivane kiseline i DDM-a. Rezultati prikazani u ovom radu za cikloheks-1-enilkarbonsku i 2-methil-cikloheks-1-enilkarbonsku kiselinu su upoređeni sa kinetičkim podacima za benzoevu kiselinu, dobijenim u istoj hemijskoj reakciji pod istim eksperimentalnim uslovima. .
Ključne reči:
cyclohex-1-enylcarboxylic acid / 2-methylcyclohex-1-enylcarboxylic acid / diazodiphenyulmethane / kinetic measurements / protic and aprotic solventsIzvor:
Journal of the Serbian Chemical Society, 2000, 65, 12, 839-846Izdavač:
- Serbian Chemical Society, Belgrade
Institucija/grupa
Tehnološko-metalurški fakultetTY - JOUR AU - Nikolić, Jasmina AU - Ušćumlić, Gordana AU - Krstić, Vera V. PY - 2000 UR - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/285 AB - Rate constants for the reaction of diazodiphenylmethane with cyclohex-1-enylcarboxylic acid and 2-methylcyclohex-1-enylcarboxylic acid were determined in nine aprotic solvents, as well as in seven protic solvents, at 30 ºC using the appropriate UV-spectroscopic method. In protic solvents the unsubsituted acid displayed higher reaction rates than the methyl-substituted one. The results in aprotic solvents showed quite the opposite, and the reaction rates were considerably lower. In order to explain the obtained results through solvent effects, reaction rate constants (k) of the examined acids were correlated using the total solvatochromic equation of the form: log k = log k0 + sπ* + aα + bβ, where π* is the measure of the solvent polarity, α represents the scale of the solvent hydrogen bond donor acidities (HBD) and β represents the scale of the solvent hydrogen bond acceptor basicities (HBA). The correlation of the kinetic data were carried out by means of multiple linear regression analysis and the opposite effects of aprotic solvents, as well as the difference in the influence of protic and aprotic solvents on the reaction of the two examined acids with DDM were discussed. The results presented in this paper for cyclohex-1-enylcarboxylic and 2-methylcyclohex-1-enylcarboxylic acids were compared with the kinetic data for benzoic acid obtained in the same chemical reaction, under the same experimental conditions. . AB - Konstante brzine za reakciju između diazodifenilmetana (DDM) i cikloheks-1-enilkarbonske, kao i 2-methilcikloheks-1-enilkarbonske kiseline su određene u devet aprotičnih i sedam protičnih rastvarača, odgovarajućom UV-spektrofotometrijskom metodom. U protičnim rastvaračima nesupstituisana kiselina je pokazala veće reakcione brzine od supstituisane. Rezultati u aprotičnim rastvaračima su pokazali upravo suprotno i brzine su znatno manje. Da bi se dobijeni rezultati objasnili kroz efekte rastvarača, konstante brzine reakcije (k) su korelisane totalnom solvatohromnom jednačinom oblika: log k = log k0 + sπ* + aα + bβ, gde je π* mera polarnosti rastvarača, α predstavlja skalu baznosti rastvarača kao akceptora protona u vodoničnoj vezi, a β predstavlja skalu kiselosti rastvarača kao donora protona u vodoničnoj vezi. Korelacija kinetičkih podataka je izvršena metodom multiple linearne regresije i razmatrani su suprotni efekti aprotičnih rastvarača, kao i razlika u uticaju protičnih i aprotičnih rastvarača na reakciju dve ispitivane kiseline i DDM-a. Rezultati prikazani u ovom radu za cikloheks-1-enilkarbonsku i 2-methil-cikloheks-1-enilkarbonsku kiselinu su upoređeni sa kinetičkim podacima za benzoevu kiselinu, dobijenim u istoj hemijskoj reakciji pod istim eksperimentalnim uslovima. . PB - Serbian Chemical Society, Belgrade T2 - Journal of the Serbian Chemical Society T1 - Reactivity of cyclohex-1-enylcarboxylic and 2-methylcyclohex-1-enylcarboxylic acids with diazodiphenylmethane in aprotic solvents T1 - Reaktivnost cikloheks-1-enilkarbonske i 2-metilcikloheks-1-enilkarbonske kiseline sa diazodifenilmetanom u aprotičnim rastvaračima EP - 846 IS - 12 SP - 839 VL - 65 UR - https://hdl.handle.net/21.15107/rcub_technorep_285 ER -
@article{ author = "Nikolić, Jasmina and Ušćumlić, Gordana and Krstić, Vera V.", year = "2000", abstract = "Rate constants for the reaction of diazodiphenylmethane with cyclohex-1-enylcarboxylic acid and 2-methylcyclohex-1-enylcarboxylic acid were determined in nine aprotic solvents, as well as in seven protic solvents, at 30 ºC using the appropriate UV-spectroscopic method. In protic solvents the unsubsituted acid displayed higher reaction rates than the methyl-substituted one. The results in aprotic solvents showed quite the opposite, and the reaction rates were considerably lower. In order to explain the obtained results through solvent effects, reaction rate constants (k) of the examined acids were correlated using the total solvatochromic equation of the form: log k = log k0 + sπ* + aα + bβ, where π* is the measure of the solvent polarity, α represents the scale of the solvent hydrogen bond donor acidities (HBD) and β represents the scale of the solvent hydrogen bond acceptor basicities (HBA). The correlation of the kinetic data were carried out by means of multiple linear regression analysis and the opposite effects of aprotic solvents, as well as the difference in the influence of protic and aprotic solvents on the reaction of the two examined acids with DDM were discussed. The results presented in this paper for cyclohex-1-enylcarboxylic and 2-methylcyclohex-1-enylcarboxylic acids were compared with the kinetic data for benzoic acid obtained in the same chemical reaction, under the same experimental conditions. ., Konstante brzine za reakciju između diazodifenilmetana (DDM) i cikloheks-1-enilkarbonske, kao i 2-methilcikloheks-1-enilkarbonske kiseline su određene u devet aprotičnih i sedam protičnih rastvarača, odgovarajućom UV-spektrofotometrijskom metodom. U protičnim rastvaračima nesupstituisana kiselina je pokazala veće reakcione brzine od supstituisane. Rezultati u aprotičnim rastvaračima su pokazali upravo suprotno i brzine su znatno manje. Da bi se dobijeni rezultati objasnili kroz efekte rastvarača, konstante brzine reakcije (k) su korelisane totalnom solvatohromnom jednačinom oblika: log k = log k0 + sπ* + aα + bβ, gde je π* mera polarnosti rastvarača, α predstavlja skalu baznosti rastvarača kao akceptora protona u vodoničnoj vezi, a β predstavlja skalu kiselosti rastvarača kao donora protona u vodoničnoj vezi. Korelacija kinetičkih podataka je izvršena metodom multiple linearne regresije i razmatrani su suprotni efekti aprotičnih rastvarača, kao i razlika u uticaju protičnih i aprotičnih rastvarača na reakciju dve ispitivane kiseline i DDM-a. Rezultati prikazani u ovom radu za cikloheks-1-enilkarbonsku i 2-methil-cikloheks-1-enilkarbonsku kiselinu su upoređeni sa kinetičkim podacima za benzoevu kiselinu, dobijenim u istoj hemijskoj reakciji pod istim eksperimentalnim uslovima. .", publisher = "Serbian Chemical Society, Belgrade", journal = "Journal of the Serbian Chemical Society", title = "Reactivity of cyclohex-1-enylcarboxylic and 2-methylcyclohex-1-enylcarboxylic acids with diazodiphenylmethane in aprotic solvents, Reaktivnost cikloheks-1-enilkarbonske i 2-metilcikloheks-1-enilkarbonske kiseline sa diazodifenilmetanom u aprotičnim rastvaračima", pages = "846-839", number = "12", volume = "65", url = "https://hdl.handle.net/21.15107/rcub_technorep_285" }
Nikolić, J., Ušćumlić, G.,& Krstić, V. V.. (2000). Reactivity of cyclohex-1-enylcarboxylic and 2-methylcyclohex-1-enylcarboxylic acids with diazodiphenylmethane in aprotic solvents. in Journal of the Serbian Chemical Society Serbian Chemical Society, Belgrade., 65(12), 839-846. https://hdl.handle.net/21.15107/rcub_technorep_285
Nikolić J, Ušćumlić G, Krstić VV. Reactivity of cyclohex-1-enylcarboxylic and 2-methylcyclohex-1-enylcarboxylic acids with diazodiphenylmethane in aprotic solvents. in Journal of the Serbian Chemical Society. 2000;65(12):839-846. https://hdl.handle.net/21.15107/rcub_technorep_285 .
Nikolić, Jasmina, Ušćumlić, Gordana, Krstić, Vera V., "Reactivity of cyclohex-1-enylcarboxylic and 2-methylcyclohex-1-enylcarboxylic acids with diazodiphenylmethane in aprotic solvents" in Journal of the Serbian Chemical Society, 65, no. 12 (2000):839-846, https://hdl.handle.net/21.15107/rcub_technorep_285 .