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 language | English (US) |
|---|---|
| Pages (from-to) | 1531-1540 |
| Number of pages | 10 |
| Journal | Journal of the Chemical Society. Perkin Transactions 2 |
| Issue number | 10 |
| State | Published - 1991 |
| Externally published | Yes |
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- Chemistry(all)
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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. / Razyńska, Anna; Rak, Janusz; Fronticelli, Clara; Bucci, Enrico.
In: Journal of the Chemical Society. Perkin Transactions 2, No. 10, 1991, p. 1531-1540.Research output: Contribution to journal › Article
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TY - JOUR
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
N2 - 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.
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.
UR - http://www.scopus.com/inward/record.url?scp=37049090757&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=37049090757&partnerID=8YFLogxK
M3 - Article
AN - SCOPUS:37049090757
SP - 1531
EP - 1540
JO - Journal of the Chemical Society, Perkin Transactions 2
JF - Journal of the Chemical Society, Perkin Transactions 2
SN - 1470-1820
IS - 10
ER -