Attempted synthesis of esters of tricarballylic acid and 3,5-dibromosalicylic acid. Structure and properties of tricarballylic acid, its anhydrides and some of their derivatives, and an investigation of the reaction pathways of anhydride formation by 1H NMR spectroscopy, MNDO and molecular mechanics methods

Anna Razyńska, Janusz Rak, Clara Fronticelli, Enrico Bucci

Research output: Contribution to journalArticle

Abstract

Reactions ordinarily leading to the formation of esters of carboxy acids afford, in the case of tricarballylic acid, the cyclic anhydride. A comparison of the experimental and simulated 1H NMR spectra reveals that the product contains a five-membered ring structure. To explain the experimental findings, theoretical calculations were performed at the level of molecular mechanics and MNDO methods, in order to obtain information on the structure and thermodynamic stability of various substrate conformations and reaction products, as well as on the reaction pathways of anhydride formation. Theoretical predictions reveal that the formation of the five-membered ring structure is preferred in the case of tricarballylic acid anhydride.

Original languageEnglish (US)
Pages (from-to)1531-1540
Number of pages10
JournalJournal of the Chemical Society. Perkin Transactions 2
Issue number10
StatePublished - 1991
Externally publishedYes

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Molecular mechanics
Anhydrides
Nuclear magnetic resonance spectroscopy
Esters
Derivatives
Reaction products
Conformations
Thermodynamic stability
Nuclear magnetic resonance
Acids
Substrates
3,5-dibromosalicylic acid
tricarballylic acid

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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abstract = "Reactions ordinarily leading to the formation of esters of carboxy acids afford, in the case of tricarballylic acid, the cyclic anhydride. A comparison of the experimental and simulated 1H NMR spectra reveals that the product contains a five-membered ring structure. To explain the experimental findings, theoretical calculations were performed at the level of molecular mechanics and MNDO methods, in order to obtain information on the structure and thermodynamic stability of various substrate conformations and reaction products, as well as on the reaction pathways of anhydride formation. Theoretical predictions reveal that the formation of the five-membered ring structure is preferred in the case of tricarballylic acid anhydride.",
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T1 - Attempted synthesis of esters of tricarballylic acid and 3,5-dibromosalicylic acid. Structure and properties of tricarballylic acid, its anhydrides and some of their derivatives, and an investigation of the reaction pathways of anhydride formation by 1H NMR spectroscopy, MNDO and molecular mechanics methods

AU - Razyńska, Anna

AU - Rak, Janusz

AU - Fronticelli, Clara

AU - Bucci, Enrico

PY - 1991

Y1 - 1991

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AB - Reactions ordinarily leading to the formation of esters of carboxy acids afford, in the case of tricarballylic acid, the cyclic anhydride. A comparison of the experimental and simulated 1H NMR spectra reveals that the product contains a five-membered ring structure. To explain the experimental findings, theoretical calculations were performed at the level of molecular mechanics and MNDO methods, in order to obtain information on the structure and thermodynamic stability of various substrate conformations and reaction products, as well as on the reaction pathways of anhydride formation. Theoretical predictions reveal that the formation of the five-membered ring structure is preferred in the case of tricarballylic acid anhydride.

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