Investigation of electronic effects in the reaction of diazodiphenylmethane with pyridine and pyridine N-oxide carboxylic acids

Autor:	Živorad D. Tadić, M. Muškatriović, Djordje M. Dimitrijević, Milica Mišić-Vuković
Rok vydání:	1974
Předmět:	chemistry.chemical_compound Diazodiphenylmethane chemistry Hydrogen bond Intramolecular force Pyridine Electronic effect Polar effect Pyridine-N-oxide Organic chemistry Alkaline hydrolysis (body disposal) Medicinal chemistry
Zdroj:	J. Chem. Soc., Perkin Trans. 2. :1051-1055
ISSN:	1364-5471 0300-9580
DOI:	10.1039/p29740001051
Popis:	The empirical Hammett treatment has been applied to the investigation of structure–reactivity relationships for pyridine and pyridine N-oxide carboxylic acids in the reaction with diazodiphenylmethane. The values obtained for the pyridine aza-group (σ2 0·878, σ3 0·740, σ41·105) are in good agreement with the literature values for the alkaline hydrolysis of the corresponding esters. For the N-oxide group, the σ values for the 3- and 4-positions (σ3 1·312, σ41·140) indicate that the overall effect is electron withdrawing. The negative value for the 2-position (σ2–0·395) can be explained on the basis of intramolecular hydrogen bonding. It is also shown that the Hammett relationship holds for pyridinecarboxylic acids with a fixed ortho-substituent as well.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::de8d760a692720bbd5074d06b7f9fbb6 https://doi.org/10.1039/p29740001051 Zobrazit plný text záznamu