Abstract
Conformational studies of symmetric diesters, dimethyl maleate, dimethyl 5,6-isopropylidenedioxybicyclo[2.2.1]hepta-2-ene- 2,3-dicarboxylate, and dimethyl succinate have been performed. It was found that the conformation wherein one of the carbonyl oxygens interacts with the carbon of the other carbonyl is the most stable in all the cases. In particular, in dimethyl maleate and dimethyl 5,6- isopropylidenedioxybicyclo[2.2.1]hepta-2-ene-2,3-dicarboxylate, it was found that the structures wherein one of the carbonyl groups is oriented near-perpendicular with respect to the C=C bond and the other carbonyl group is oriented near-parallel with respect to the C=C bond have the lowest energies, showing good agreement with the X-ray crystal structures. Bonding interaction between the carbonyl oxygen and the other carbonyl carbon was also found in all these structures. These results suggest the existence of the n->π* interaction between the two carbonyl groups and are expected to provide insight into the non-covalent interaction between the two carbonyl groups in these symmetric diesters.
Keywords: Carbonyl group, Conformation, n->π* interaction; Selectivity, Symmetric diesters, Theoretical studies
Call for Papers in Thematic Issues
Advances of Heterocyclic Chemistry with Pesticide Activity
Global food safety and security will continue to be a global concern for the next 50 years and beyond. Plant diseases have had a significant impact on food safety and security throughout the entire food chain, from primary production to consumption. While conventional chemical pesticides have been traditionally used for ...read more
Calculation design of covalent/metal organic framework based catalysts
This research area combines theoretical computation and screening with machine learning for the design of covalent/metal organic framework-based catalysts, bridging the disciplines of organic chemistry, physical chemistry, computational chemistry, materials science, and machine learning. It covers several critical aspects: designing and synthesizing organic catalysts for improved performance, applying computational methods ...read more
Carbohydrates conversion in biofuels and bioproducts
Biomass pretreatment, hydrolysis, and saccharification of carbohydrates, and sugars bioconversion in biofuels and bioproducts within a biorefinery framework. Carbohydrates derived from woody biomass, agricultural wastes, algae, sewage sludge, or any other lignocellulosic feedstock are included in this issue. Simulation, techno-economic analysis, and life cycle analysis of a biorefinery process are ...read more
Catalytic C-H bond activation as a tool for functionalization of heterocycles
The major topic is the functionalization of heterocycles through catalyzed C-H bond activation. The strategies based on C-H activation not only provide straightforward formation of C-C or C-X bonds but, more importantly, allow for the avoidance of pre-functionalization of one or two of the cross-coupling partners. The beneficial impact of ...read more
Related Books
Advances in Organic Synthesis
The Synthetic Methods, Structures, and Properties of the Ca-C σ Bond Organocalcium Containing Compounds
Advances in Organic Synthesis
Chemistry of Bipyrazoles: Synthesis and Applications
Advances in Organic Synthesis
Advanced Nanocatalysis for Organic Synthesis and Electroanalysis
Advances in Organic Synthesis
Advances in Organic Synthesis
12