Enthalpy-entropy compensation combined with cohesive free-energy densities for tuning the melting temperatures of cyanobiphenyl derivatives
This work illustrates how minor structural perturbations produced by methylation of 4′-(dodecyloxy)-4-cyanobiphenyl leads to enthalpy-entropy compensation for their melting processes, a trend which can be analyzed within the frame of a simple intermolecular cohesive model. The transformation of the melting thermodynamic parameters collected at variable temperatures into cohesive free-energy densities expressed at a common reference temperature results in a novel linear correlation, from which melting temperatures can be simply predicted from molecular volumes. In tune with temperature! The transformation of the melting thermodynamic parameters into cohesive free-energy densities (CFED) for 4′-(n-oxy)-i′-methyl-j-methyl-4-cyanobiphenyl (CnLi′,j) provides a novel linear correlation for predicting melting temperatures in a simple way. Copyright
Dutronc, Thibault,Terazzi, Emmanuel,Guenee, Laure,Buchwalder, Kerry-Lee,Spoerri, Aurore,Emery, Daniel,Mareda, Jiri,Floquet, Sebastien,Piguet, Claude
p. 8447 - 8456
(2013/07/19)
Enantioenriched synthesis of Escitalopram using lithiation-borylation methodology
The asymmetric synthesis of Escitalopram has been completed using a lithiation-borylation reaction as the key step. Suitably functionalized enantioenriched carbamate (er 98:2) and boronic ester coupling partners were prepared and following deprotonation with s-BuLi and borylation, the tertiary alcohol was obtained in 42% yield and 93:7 er. The lithiation-borylation reaction was found to tolerate nitrile, benzylic alcohol and N-Boc functionalities. The tertiary alcohol was converted to Escitalopram in three further steps.
Partridge, Benjamin M.,Thomas, Stephen P.,Aggarwal, Varinder K.
p. 10082 - 10088
(2012/02/05)
Modular Solid-Phase Synthetic Approach to Optimize Structural and Electronic Properties of Oligoboronic Acid Receptors and Sensors for the Aqueous Recognition of Oligosaccharides
This article describes the design and optimization of the first entirely modular, parallel solid-phase synthetic approach for the generation of well-defined polyamine oligoboronic acid receptors and fluorescence sensors for complex oligosaccharides. The s
Stones, Duane,Manku, Sukhdev,Lu, Xiaosong,Hall, Dennis G.
p. 92 - 100
(2007/10/03)
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