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A polar nature of benzoic acids extrusion from nitroalkyl benzoates: DFT mechanistic study.

Jasiński R, Kącka A - J Mol Model (2015)

Bottom Line: It was discovered, that these reactions proceed via polar, but one-step mechanism.It turned out that depending on the nature of the substituent in the ester molecule and on medium polarity, the studied reactions may take place via transition states with varied synchronicity—from E1-like structures, to E1cb-like structures.A purely ionic, two-stage mechanism was not identified in any of the cases.

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Affiliation: Institute of Organic Chemistry and Technology, Cracow University of Technology,, Warszawska 24, 31-155, Cracow, Poland, radomir@chemia.pk.edu.pl.

ABSTRACT
Using DFT calculations at various theory levels, quantum-chemical simulations of decomposition paths were performed for a series of nitroalkyl benzoates. It was discovered, that these reactions proceed via polar, but one-step mechanism. It turned out that depending on the nature of the substituent in the ester molecule and on medium polarity, the studied reactions may take place via transition states with varied synchronicity—from E1-like structures, to E1cb-like structures. A purely ionic, two-stage mechanism was not identified in any of the cases.

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Benzoic acids extrusion from nitroalkyl benzoates
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Sch1: Benzoic acids extrusion from nitroalkyl benzoates

Mentions: The most universal strategies for their synthesis are based on the decomposition of esters of appropriate β-nitroalcohols [4]. These may be, e.g., benzoic acid esters [9], which are easy to synthesize and isolate (e.g., Scheme 1).Scheme 1


A polar nature of benzoic acids extrusion from nitroalkyl benzoates: DFT mechanistic study.

Jasiński R, Kącka A - J Mol Model (2015)

Benzoic acids extrusion from nitroalkyl benzoates
© Copyright Policy - OpenAccess
Related In: Results  -  Collection

Show All Figures
getmorefigures.php?uid=PMC4339780&req=5

Sch1: Benzoic acids extrusion from nitroalkyl benzoates
Mentions: The most universal strategies for their synthesis are based on the decomposition of esters of appropriate β-nitroalcohols [4]. These may be, e.g., benzoic acid esters [9], which are easy to synthesize and isolate (e.g., Scheme 1).Scheme 1

Bottom Line: It was discovered, that these reactions proceed via polar, but one-step mechanism.It turned out that depending on the nature of the substituent in the ester molecule and on medium polarity, the studied reactions may take place via transition states with varied synchronicity—from E1-like structures, to E1cb-like structures.A purely ionic, two-stage mechanism was not identified in any of the cases.

View Article: PubMed Central - PubMed

Affiliation: Institute of Organic Chemistry and Technology, Cracow University of Technology,, Warszawska 24, 31-155, Cracow, Poland, radomir@chemia.pk.edu.pl.

ABSTRACT
Using DFT calculations at various theory levels, quantum-chemical simulations of decomposition paths were performed for a series of nitroalkyl benzoates. It was discovered, that these reactions proceed via polar, but one-step mechanism. It turned out that depending on the nature of the substituent in the ester molecule and on medium polarity, the studied reactions may take place via transition states with varied synchronicity—from E1-like structures, to E1cb-like structures. A purely ionic, two-stage mechanism was not identified in any of the cases.

No MeSH data available.